JP5308609B2 - ポリマー遷移金属錯体及びその用途 - Google Patents
ポリマー遷移金属錯体及びその用途 Download PDFInfo
- Publication number
- JP5308609B2 JP5308609B2 JP2001538538A JP2001538538A JP5308609B2 JP 5308609 B2 JP5308609 B2 JP 5308609B2 JP 2001538538 A JP2001538538 A JP 2001538538A JP 2001538538 A JP2001538538 A JP 2001538538A JP 5308609 B2 JP5308609 B2 JP 5308609B2
- Authority
- JP
- Japan
- Prior art keywords
- transition metal
- metal complex
- polymer
- ligand
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 229910052723 transition metal Inorganic materials 0.000 title claims abstract description 143
- 150000003624 transition metals Chemical class 0.000 title claims abstract description 129
- 229920000642 polymer Polymers 0.000 title claims description 147
- 239000003446 ligand Substances 0.000 claims abstract description 104
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 35
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052742 iron Inorganic materials 0.000 claims abstract description 14
- 229910052762 osmium Inorganic materials 0.000 claims abstract description 14
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 14
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 13
- 239000010941 cobalt Substances 0.000 claims abstract description 13
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 13
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical class N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims abstract description 7
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims abstract 9
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000006850 spacer group Chemical group 0.000 claims description 54
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 34
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 13
- 150000002500 ions Chemical class 0.000 claims description 13
- 125000000524 functional group Chemical group 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 125000002015 acyclic group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 8
- HVEHTNLSYGZELD-UHFFFAOYSA-N 2,2'-biimidazole Chemical compound N1=CC=NC1=C1N=CC=N1 HVEHTNLSYGZELD-UHFFFAOYSA-N 0.000 claims description 7
- SZXUTTGMFUSMCE-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)pyridine Chemical compound C1=CNC(C=2N=CC=CC=2)=N1 SZXUTTGMFUSMCE-UHFFFAOYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 abstract description 34
- 108090000790 Enzymes Proteins 0.000 abstract description 34
- 238000012546 transfer Methods 0.000 abstract description 6
- -1 quinines (eg Chemical class 0.000 description 68
- 125000003118 aryl group Chemical group 0.000 description 41
- 239000000243 solution Substances 0.000 description 37
- 229940088598 enzyme Drugs 0.000 description 32
- 239000012491 analyte Substances 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 19
- 125000001424 substituent group Chemical group 0.000 description 19
- 125000003282 alkyl amino group Chemical group 0.000 description 18
- 125000004414 alkyl thio group Chemical group 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 18
- 125000004663 dialkyl amino group Chemical group 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000004132 cross linking Methods 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000002243 precursor Substances 0.000 description 11
- 125000005208 trialkylammonium group Chemical group 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 238000006056 electrooxidation reaction Methods 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 8
- 229920000075 poly(4-vinylpyridine) Polymers 0.000 description 8
- 238000000967 suction filtration Methods 0.000 description 8
- 239000004971 Cross linker Substances 0.000 description 7
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 7
- 125000005236 alkanoylamino group Chemical group 0.000 description 7
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 7
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 7
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
- 125000002883 imidazolyl group Chemical group 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 230000032258 transport Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 125000000033 alkoxyamino group Chemical group 0.000 description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
- 125000005276 alkyl hydrazino group Chemical group 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 229920006254 polymer film Polymers 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- KMRPQHUALQQSPI-UHFFFAOYSA-N 1-methyl-2-(1-methylimidazol-2-yl)imidazole Chemical compound CN1C=CN=C1C1=NC=CN1C KMRPQHUALQQSPI-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 229910001428 transition metal ion Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 239000004366 Glucose oxidase Substances 0.000 description 4
- 108010015776 Glucose oxidase Proteins 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- 239000013060 biological fluid Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- 229940116332 glucose oxidase Drugs 0.000 description 4
- 235000019420 glucose oxidase Nutrition 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 229920002006 poly(N-vinylimidazole) polymer Polymers 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 230000027756 respiratory electron transport chain Effects 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical group [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 4
- NVRVNSHHLPQGCU-UHFFFAOYSA-N 6-bromohexanoic acid Chemical compound OC(=O)CCCCCBr NVRVNSHHLPQGCU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 108090000854 Oxidoreductases Proteins 0.000 description 3
- 102000004316 Oxidoreductases Human genes 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 229920000388 Polyphosphate Polymers 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 210000001124 body fluid Anatomy 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000012992 electron transfer agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000010452 phosphate Chemical group 0.000 description 3
- 239000001205 polyphosphate Substances 0.000 description 3
- 235000011176 polyphosphates Nutrition 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- 238000000108 ultra-filtration Methods 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- 125000004754 (C2-C12) dialkylamino group Chemical group 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 2
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000007942 carboxylates Chemical group 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003487 electrochemical reaction Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 2
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 150000003461 sulfonyl halides Chemical class 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- ITWBWJFEJCHKSN-UHFFFAOYSA-N 1,4,7-triazonane Chemical compound C1CNCCNCCN1 ITWBWJFEJCHKSN-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 1
- ZMQPAJOWYXQIJO-UHFFFAOYSA-N 2-(1,3-oxazol-2-yl)-1,3-oxazole Chemical compound C1=COC(C=2OC=CN=2)=N1 ZMQPAJOWYXQIJO-UHFFFAOYSA-N 0.000 description 1
- SMSLWFZHCONMGQ-UHFFFAOYSA-N 2-(1,3-thiazol-2-yl)-1,3-thiazole Chemical compound C1=CSC(C=2SC=CN=2)=N1 SMSLWFZHCONMGQ-UHFFFAOYSA-N 0.000 description 1
- VEZJRJGLFIXQHG-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)-1h-benzimidazole Chemical class C1=CC=C2NC(C=3NC4=CC=CC=C4N=3)=NC2=C1 VEZJRJGLFIXQHG-UHFFFAOYSA-N 0.000 description 1
- MZXLORGBAWJZTG-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-6-methylpyridine Chemical compound CC1=CC=CC(C=2NC=CN=2)=N1 MZXLORGBAWJZTG-UHFFFAOYSA-N 0.000 description 1
- OAZFTIPKNPTDIO-UHFFFAOYSA-N 2-(6-bromohexyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCCCBr)C(=O)C2=C1 OAZFTIPKNPTDIO-UHFFFAOYSA-N 0.000 description 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 description 1
- AHIPJALLQVEEQF-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1COC(C=C1)=CC=C1N(CC1OC1)CC1CO1 AHIPJALLQVEEQF-UHFFFAOYSA-N 0.000 description 1
- HCTCBELJQDBBDK-UHFFFAOYSA-N 4-bromo-1-oxido-2-pyridin-2-ylpyridin-1-ium Chemical compound [O-][N+]1=CC=C(Br)C=C1C1=CC=CC=N1 HCTCBELJQDBBDK-UHFFFAOYSA-N 0.000 description 1
- SCOXFIBXWCCICG-UHFFFAOYSA-N 4-bromo-2-pyridin-2-ylpyridine Chemical group BrC1=CC=NC(C=2N=CC=CC=2)=C1 SCOXFIBXWCCICG-UHFFFAOYSA-N 0.000 description 1
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical group NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 description 1
- IMEVSAIFJKKDAP-UHFFFAOYSA-N 4-methoxy-2-(4-methoxypyridin-2-yl)pyridine Chemical group COC1=CC=NC(C=2N=CC=C(OC)C=2)=C1 IMEVSAIFJKKDAP-UHFFFAOYSA-N 0.000 description 1
- UQMWXMROSLGYMV-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)imidazol-1-yl]hexan-1-amine Chemical compound CC1=CC=CC(C=2N(C=CN=2)CCCCCCN)=N1 UQMWXMROSLGYMV-UHFFFAOYSA-N 0.000 description 1
- AHISYUZBWDSPQL-UHFFFAOYSA-N 6-methylpyridine-2-carbaldehyde Chemical compound CC1=CC=CC(C=O)=N1 AHISYUZBWDSPQL-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- MHXILWYZDDCNCF-UHFFFAOYSA-N BrC1=CC(=NC=C1)C1=NC=CC=C1.NCCCCCCNC1=CC(=NC=C1)C1=NC=CC=C1 Chemical group BrC1=CC(=NC=C1)C1=NC=CC=C1.NCCCCCCNC1=CC(=NC=C1)C1=NC=CC=C1 MHXILWYZDDCNCF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- SIHMYDNKXLSGGF-UHFFFAOYSA-N CC1=CC=CC(=N1)C=1NC=CN1.N1C=NC=C1 Chemical compound CC1=CC=CC(=N1)C=1NC=CN1.N1C=NC=C1 SIHMYDNKXLSGGF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000016938 Catalase Human genes 0.000 description 1
- 108010053835 Catalase Proteins 0.000 description 1
- 241000157855 Cinchona Species 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- YPZRHBJKEMOYQH-UYBVJOGSSA-N FADH2 Chemical compound C1=NC2=C(N)N=CN=C2N1[C@@H]([C@H](O)[C@@H]1O)O[C@@H]1COP(O)(=O)OP(O)(=O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C(NC(=O)NC2=O)=C2NC2=C1C=C(C)C(C)=C2 YPZRHBJKEMOYQH-UYBVJOGSSA-N 0.000 description 1
- 102000003983 Flavoproteins Human genes 0.000 description 1
- 108010057573 Flavoproteins Proteins 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920003060 Poly(vinyl benzyl chloride) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 108010039918 Polylysine Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 229910018557 Si O Inorganic materials 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000007860 aryl ester derivatives Chemical group 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000004054 benzoquinones Chemical class 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229940075397 calomel Drugs 0.000 description 1
- 150000001718 carbodiimides Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 229910021419 crystalline silicon Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical compound Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- VGKQJCSDERXWRV-UHFFFAOYSA-H dipotassium;hexachloroosmium(2-) Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[K+].[K+].[Os+4] VGKQJCSDERXWRV-UHFFFAOYSA-H 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000007812 electrochemical assay Methods 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- IFQUWYZCAGRUJN-UHFFFAOYSA-N ethylenediaminediacetic acid Chemical compound OC(=O)CNCCNCC(O)=O IFQUWYZCAGRUJN-UHFFFAOYSA-N 0.000 description 1
- 210000003722 extracellular fluid Anatomy 0.000 description 1
- UPBDXRPQPOWRKR-UHFFFAOYSA-N furan-2,5-dione;methoxyethene Chemical compound COC=C.O=C1OC(=O)C=C1 UPBDXRPQPOWRKR-UHFFFAOYSA-N 0.000 description 1
- 235000012209 glucono delta-lactone Nutrition 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000002443 hydroxylamines Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 239000012633 leachable Substances 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- ULPRAVBXAIWFAY-UHFFFAOYSA-N n'-(2-pyridin-2-ylpyridin-4-yl)hexane-1,6-diamine Chemical compound NCCCCCCNC1=CC=NC(C=2N=CC=CC=2)=C1 ULPRAVBXAIWFAY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 150000002908 osmium compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229940085991 phosphate ion Drugs 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000656 polylysine Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000003410 quininyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 235000019830 sodium polyphosphate Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B5/00—Measuring for diagnostic purposes; Identification of persons
- A61B5/145—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue
- A61B5/1486—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue using enzyme electrodes, e.g. with immobilised oxidase
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/005—Compounds of elements of Group 5 of the Periodic Table without metal-carbon linkages
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B5/00—Measuring for diagnostic purposes; Identification of persons
- A61B5/145—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue
- A61B5/14532—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue for measuring glucose, e.g. by tissue impedance measurement
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B5/00—Measuring for diagnostic purposes; Identification of persons
- A61B5/145—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue
- A61B5/1468—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue using chemical or electrochemical methods, e.g. by polarographic means
- A61B5/1477—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue using chemical or electrochemical methods, e.g. by polarographic means non-invasive
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/002—Osmium compounds
- C07F15/0026—Osmium compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/001—Enzyme electrodes
- C12Q1/004—Enzyme electrodes mediator-assisted
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Public Health (AREA)
- Optics & Photonics (AREA)
- Heart & Thoracic Surgery (AREA)
- Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Pathology (AREA)
- Veterinary Medicine (AREA)
- Medical Informatics (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Genetics & Genomics (AREA)
- General Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Immunology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Emergency Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pyridine Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Absorbent Articles And Supports Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、ポリマー遷移金属錯体ならびに酸化還元メディエーターとしての使用などのそれの使用に関する。さらに本発明は、スペーサーを介してポリマー骨格に結合した遷移金属錯体に関するものでもある。
酵素系電気化学的センサーは、臨床、環境、農学及び生物工学的な応用において分析対象(analyte)の検出に広く用いられている。ヒト体液の臨床学的アッセイで測定し得る分析対象としては、例えば、グルコース、乳酸、コレステロール、ビリルビン及びアミノ酸がある。血液のような生物流体中のこれらの分析対象の濃度は、疾病の診断及び監視に重要である。
本発明は、新規なポリマー遷移金属錯体及びその酸化還元ポリマー及び酸化還元メディエーターとしての用途に関する。酸化還元ポリマーは、酵素と電極との間で電子を運搬することができる。該ポリマーは、電気化学バイオセンサーにおいて有用となり得る。
a)ポリマー骨格及びそのポリマー骨格から延びる複数のペンダント基を有するポリマーであって、ペンダント基の少なくとも一部が反応性基を有するポリマーと、
b)複数の遷移金属錯体であって、各遷移金属錯体が下記式の構造を有する錯体との反応生成物を含むポリマー遷移金属錯体である。
さらに別の実施形態は、前記酸化還元メディエーター、作用電極及び対電極を有するセンサーである。前記酸化還元メディエーターは、作業電極に近接して配置する。好ましくは前記酸化還元メディエーターは、作業電極上に配置する。より好ましくは前記酸化還元メディエーターは、浸出しない形で作業電極上に配置される。
本発明は、ポリマー遷移金属錯体及びその酸化還元メディエーターとしての用途に関する。さらに本発明は、スペーサーを介してポリマー骨格に結合した遷移金属錯体に関する。本発明はさらに、ポリマー遷移金属錯体の調製に関するものでもある。少なくとも一部の実施例において、前記ポリマー遷移金属錯体は、特定の範囲の酸化還元電位、ならびに電極と急速に電子を交換し、酸化還元酵素または別の分析対象に特異的な酸化還元触媒存在下で分析対象(analyte)の電気酸化または電気還元の速度論を促進する能力という特徴のうちの1つ以上を有する。
「アルキル」という用語は、直鎖または分岐の飽和脂肪族炭化水素を含む。アルキル基の例としては、メチル、エチル、n−プロピル、イソプロピル、n−ブチル、tert−ブチルなどがある。別段の断りがない限り、「アルキル」という用語はアルキル基及びシクロアルキル基の双方を含む。
「電気化学センサー」とは、電気化学的酸化または還元反応を介して、サンプル中の分析対象の有無を検出したり、またはその濃度または量を測定するよう構成された機器である。その反応は代表的には、分析対象の量または濃度に相関させることができる電気信号に変換することができる。
「対電極」という用語は、別段の断りがない限り、a)対電極及びb)参照電極としても機能する対電極(すなわち、対向/参照電極)の双方を含む。
ポリマー遷移金属錯体は、ポリマー骨格と、そのポリマー骨格に共有結合し、その骨格から延びているスペーサーと、それぞれが前記スペーサーのいずれかに共有結合している少なくとも1個の配位子とを備える遷移金属錯体を含む。好適な遷移金属錯体の例としては、米国特許第5,262,035号、同第5,262,305号、同第5,320,725号、同第5,365,786号、同第5,378,628号、同第5,393,903号、同第5,593,852号、同第5,665,222号、同第5,972,199号及び同第6,143,164号、米国特許出願09/034372号、同第09/070677号、同第09/295962号及び同第09/434026号、米国仮特許出願60/165565号ならびに本願と同日に出願の「イミダゾール環を有する二座配位子との遷移金属錯体(Transition Metal Complexes with Bidentate Ligand having an Imidazole Ring)」と題された米国特許出願 号(これらはいずれも、引用によって本明細書に含まれる)に記載のものなどがある。
(A)2個の一座配位子及び2個の二座配位子、
(B)4個の一座配位子及び1個の二座配位子、
(C)3個の一座配位子及び1個の三座配位子、
(D)1個の一座配位子、1個の二座配位子及び1個の三座配位子、
(E)2個の一座配位子及び1個の四座配位子、ならびに
などがある。
電子輸送には、電極上に配置された架橋フィルムにおける酸化還元ポリマーの部分間(例:上記のように、ポリマー骨格に結合した1つ以上の遷移金属錯体)での電子の交換が関与する。遷移金属錯体は、共有結合、配位結合またはイオン結合を介してポリマー骨格に結合することができるが、共有結合及び配位結合が好ましい。電子交換は、例えば架橋酸化還元ポリマーフィルムの異なる部分の衝突を介して起こる。遷移金属錯体ポリマーを介して輸送される電子は、例えばグルコースオキシダーゼによるグルコースの酸化のような酵素基質の電気酸化から由来し得る。
遷移金属錯体は、錯体及びポリマー骨格上の反応性基の有効性(availability)及び性質に応じて、ポリマー骨格に直接または間接的に結合し得る。例えばポリ(4−ビニルピリジン)におけるピリジン基またはポリ(N−ビニルイミダゾール)におけるイミダゾール基は、一座配位子として作用できることから、金属中心に直接結合することができる。別の形態として、ポリ(4−ビニルピリジン)におけるピリジン基またはポリ(N−ビニルイミダゾール)におけるイミダゾール基は、活性化することで、遷移金属錯体のアミンなどの反応性基と共有結合を形成することができるカルボキシレート官能基などの好適な反応性基を有する置換アルキル部分と四級化(quaternized)され得る(反応性基の他の例のリストについては表1を参照されたい)。
電極において酸化還元メディエーターとして使用される遷移金属錯体は、例えばFe3+またはZn2+などの分析試料中の遷移金属の存在によって影響を受け得る。電極の試験を行うのに使用される緩衝液への遷移金属陽イオンの添加によって、得られる電流が低下する。電流低下の程度は、遷移金属陽イオンを沈殿させる緩衝液中の陰イオンの有無によって決まる。サンプル溶液中での遷移金属の残留濃度が低いほど、電流はより安定となる。遷移金属陽イオンの沈殿を助ける陰イオンには、例えばリン酸イオンなどがある遷移金属陽イオン添加による電流低下は、非リン酸緩衝液中で最も顕著であることが認められている。電極を、遷移金属陽イオンを含む緩衝液から遷移金属陽イオンを含まない緩衝液に移すと、元の電流が回復する。
グルコースオキシダーゼは、二酸素(dioxygen)によるD−グルコースのD−グルコノ−1,5−ラクトンと過酸化水素への酸化を触媒するフラボタンパク酵素である。例えばFe2+などの還元型遷移金属陽イオン及び一部の遷移金属錯体は、過酸化水素と反応し得る。その反応によって、有害なOHラジカル及び相当する酸化された陽イオンが形成される。新たに形成されたこれらの遷移金属陽イオンが存在すると酵素が阻害される場合があり、その陽イオンは金属錯体と反応し得る。さらに、酸化遷移金属陽イオンは、酵素のFADH2中心によって、または遷移金属錯体によって還元され得る。
別段の断りがない限り、化学試薬はいずれも、アルドリッチ・ケミカルズ社(Aldrich Chemical Co., Milwaukee, WI)その他の入手先から入手可能である。
混合物を90℃で3〜4時間撹拌することで、化合物H(10%スチレン、アルドリッチ(Aldrich))(2.37g)をDMF(20mL)に溶かした。6−ブロモヘキサン酸(0.66g)を10分間かけて滴下し、得られた溶液を90℃で24時間撹拌した。溶液をEtOAc300mLに投入し、沈殿を吸引濾過によって回収した。ガム状生成物を最小量のメタノールに再度溶かし、エーテル(200mL)で析出させた。生成物を50℃で高真空下に2日間乾燥させた。
温度計及び滴下漏斗を取り付けた250mLの三つ首丸底フラスコ中、6−メチルピリジン−2−カルボキシアルデヒド(26g、0.21mol)及びグリオキサール(40%、30mL)のEtOH(50mL)溶液を、NaCl/氷浴で撹拌した。溶液が冷却されて5℃以下となった時点で、滴下漏斗から濃NH4OHを滴下した。溶液の温度が5℃以下に維持されるように滴下速度を制御した。滴下後、黄色溶液の撹拌を氷浴で1時間、室温で終夜続けた。明黄色結晶を吸引濾過によって回収し、H2O(20mL)で洗浄した。結晶をH2O(200mL)に再懸濁させ、短時間沸騰させてから吸引濾過して生成物を回収し、それを高真空下に乾燥した。収率:35%。
2−(6−メチル−2−ピリジル)イミダゾール(2.16g)及びナトリウムt−ブトキシド(1.57g)の乾燥DMF(50mL)溶液に、N−(6−ブロモヘキシル)フタルイミド(4.72g)を加えた。得られた溶液を、室温で3時間、60℃で3.5時間撹拌した。溶液をH2O(80mL)に投入し、EtOAcで3回抽出した(100mLで3回)。合わせたEtOAc抽出液を無水Na2SO4で脱水し、溶媒留去して乾固させた。生成物について、EtOAcを溶離液として用いるシリカゲルカラムによって精製を行った。収量:約4.2g。
2−(6−メチル−2−ピリジル)−1−(6−フタルイミド)ヘキシル)イミダゾール(4.2g)のEtOH(50mL)溶液に、ヒドラジン水和物1.5mLを加えた。得られた溶液を80℃で終夜撹拌した。溶液を冷却して室温とし、吸引濾過を行って沈殿を除去した。濾液の溶媒留去を行って粗生成物を得て、それについて溶離液として5%濃NH3H2O/CH3CNを用いるシリカゲルカラム精製を行った。収量:約2.5g。
2,2′−ビイミダゾール(Fieselmann, B. F.ら、Inorg. Chem.、第17巻、2078頁(1978年))(4.6g、34.3mmol)の乾燥DMF(100mL)溶液を、氷水浴で冷却した250mL丸底フラスコ中で撹拌しながら、それにNaH(鉱油中60%品2.7g、68.6mmol)を少量ずつ加えた。溶液をN2下に0℃で1時間撹拌した後、トルエンスルホン酸メチル(10.3mL、68.6mmol)を、注射器を用いて30分間かけて少量ずつ加えた。溶液の撹拌を氷水浴で1時間、室温で3時間続けた。溶媒を減圧蒸留によって除去した。暗色残留物をエーテルで磨砕し、次に吸引濾過し、真空乾燥した。生成物を昇華によって精製した。収率:80%。
ヘキサクロロオスミウム酸カリウム(1g、2.08mmol)、1,1′−ジメチル−2,2′−ビイミダゾール(0.67g、4.16mmol)及びLiCl(1g、23.8mmol)を、還流冷却管を取り付けた250mL三つ首丸底フラスコ中でエチレングリコール40mLに懸濁させた。懸濁液をN2で15分間脱気し、N2下に油浴にて170℃で7〜8時間撹拌して、暗褐色溶液を得た。溶媒を浴温90〜100℃での高真空蒸留によって除去した。ガム状固体をアセトンで2回(50mLで2回)、H2Oで1回(50mL)磨砕した。生成物を、高真空下に50℃で24時間乾燥した。
[Os(1,1′−ジメチル−2,2′−ビイミダゾール)2Cl2]Cl(0.525g)及び1−(6−アミノヘキシル)−2−(6−メチル−2−ピリジル)イミダゾール(0.248g)のエチレングリコール(40mL)中混合物をN2で10分間脱気し、N2下140℃で24時間撹拌した。エチレングリコールを90℃での高減圧蒸留によって除去した。残留物をH2O 150mLに溶かし、得られた溶液を開放空気中で24時間撹拌して、Os(II)を完全に酸化してOs(III)とした。その溶液を、高速で攪拌されているNH4PF6(4.2g)のH2O(100mL)溶液に投入した。沈殿を吸引濾過によって回収し、H2Oで洗浄した(10mLで2回)。粗生成物をCH3CN15mLに再度溶かし、NH4PF6(2.2g)のH2O(200mL)溶液を撹拌したものに加えた。得られた沈殿を吸引濾過によって回収し、H2O(100mL)で洗浄し、高真空下に45℃で乾燥した。収量:0.6g。
化合物Gについて記載の方法を用いて、ポリマーI及び錯体Kから、ポリマーオスミウム化合物を合成した。
100mL丸底フラスコ中で酢酸30mLに溶かした4−ニトロ−2,2′−ビピリジル−N−オキサイド(Wenkert,D.、Woodward,R.B.J.、Org. chem.、第48巻、283頁(1983年))(5g)に、臭化アセチル16mLを加えた。黄色混合物を1.5時間還流させ、次にロータリーエバポレータによって乾固させた。得られた明黄色固体は、それ以上精製を行わなくとも、次の段階には十分な純度を有するものであった。収率:95%。
4−ブロモ−2,2′−ビピリジル−N−オキサイドのCHCl3(60mL)懸濁液を撹拌しながら、それにPCl3 12mLを室温で加えた。混合物をN2下に2時間還流させ、次に冷却して室温とした。反応混合物を氷水100mLに投入した。水相を分液し、保存した。CHCl3層をH2Oで3回抽出し(60mLで3回)、廃棄した。合わせた水溶液をNaHCO3粉末で中和して約pH7〜8とした。得られた白色沈殿を吸引濾過によって回収し、H2O(30mL)で洗浄し、減圧下に50℃で24時間乾燥させた。収率:85%。
250mL丸底フラスコ中の4−ブロモ−2,2′−ビピリジル(2.5g)及び1,6−ジアミノヘキサン(15g)の混合物をN2下に油浴で140℃にて4〜5時間加熱した。過剰の1,6−ジアミノヘキサンを90〜120℃での高減圧蒸留によって除去した。生成物について、5%NH4OH/イソプロピルアルコールを溶離液とするシリカゲルカラムにより精製した。収率:70%。
化合物Kについて記載の方法を用いて、4−((6−アミノヘキシル)アミノ)−2,2′−ビピリジン及び[Os(1,1′−ジメチル−2,2′−ビイミダゾール)2Cl2]Clから、化合物Nを生成した。
化合物M(37mg、International Specialty Products, Wayne, NJ, USA)のCH3CN(2mL)及びTHF(0.5mL)溶液に、化合物N(51mg)を加え、次にN,N,N−ジイソプロピルエチルアミン2滴を加えた。得られた溶液を室温で24時間撹拌した。H2O(5mL)を加え、溶液をさらに24時間撹拌した。溶液を追加のH2O(50mL)で希釈し、化合物Gの精製について前述したように繰り返し限外濾過によって透析した。透析溶液を凍結乾燥して、化合物Oを得た。
Claims (17)
- ポリマー遷移金属錯体において、
ポリマー骨格と、
複数のスペーサーであって、各スペーサーが前記ポリマー骨格に共有結合し、その骨格から延びており、各スペーサーが、−(CRrRs)−、−O−、−S−、−C(O)O−、−S(O)2NRk−、−OC(O)NRm−、−OC(S)NRn−、−C(O)NRt−、−NRu−、−CRv=N−O−、−CRw=NNRx−及び(SiRyRz)−のうちから選択される少なくとも1個の非環状官能基を含み、Rr及びRsが独立に、水素、塩素、フッ素、または置換もしくは未置換のアルキル、アルコキシ、アルケニルまたはアルキニルであり、かつRk、Rm、Rn、Rt、Ru、Rv、Rw、Rx、Ry及びRzが独立に、水素または置換もしくは未置換アルキルであるスペーサーと、
複数の遷移金属錯体であって、各遷移金属錯体が下記式の構造を有する遷移金属錯体とを有するポリマー遷移金属錯体。
【化1】
[式中、
Mはオスミウム、ルテニウム、バナジウム、コバルトまたは鉄であり、
L1は、複素環を含む配位子であり、かつ該複素環のヘテロ原子を介してMに配位結合しており、
L2、L3、L4、L5及びL6は含窒素複素環を有する配位子であって、L1、L2、L3、L4、L5及びL6はそれぞれ独立に、一座配位子であるか、または少なくとも1個の他の配位子と組み合わさって多座配位子を形成しており、
L1、L2、L3、L4、L5及びL6のうちの少なくとも一つが、前記スペーサーのいずれかに共有結合している]
- L1の前記複素環が含窒素複素環を有し、該複素環の窒素原子を介してMに配位結合している請求項1に記載のポリマー遷移金属錯体。
- 前記含窒素複素環が、置換もしくは未置換のピリジン、イミダゾール、2,2’−ビピリジン、2−(2−ピリジル)イミダゾールまたは2,2’−ビイミダゾールを有する請求項2に記載のポリマー遷移金属錯体。
- L 2 、L 3 、L 4 、L 5 及びL 6 のそれぞれが含窒素複素環を有する請求項1に記載のポリマー遷移金属錯体。
- L 1 、L 2 、L 3 、L 4 、L 5 及びL 6 のうちの少なくとも2個が組み合わさって、少なくとも1個の多座配位子を形成している請求項1に記載のポリマー遷移金属錯体。
- L 1 、L 2 、L 3 、L 4 、L 5 及びL 6 のうちの少なくとも4個が組み合わさって、置換及び未置換の2,2’−ビピリジン類、2−(2−ピリジル)イミダゾール類及び2,2’−ビイミダゾール類のうちから選択される少なくとも2個の多座配位子を形成している請求項1に記載のポリマー遷移金属錯体。
- 前記遷移金属錯体が、少なくとも1個の置換または未置換の2,2’−ビイミダゾールまたは2−(2−ピリジル)イミダゾールを有する請求項6に記載のポリマー遷移金属錯体。
- 各スペーサーが、−(CR r R s )−、−O−、−S−、−S(O) 2 NR k −、−OC(O)NR m −、−OC(S)NR n −、−C(O)NR t −及びNR u −のうちから選択される少なくとも4個の非環状官能基を有し、R k 、R m 、R n 、R r 、R s 、R t 及びR u が独立に、水素及び置換もしくは未置換アルキルのうちから選択される請求項1に記載のポリマー遷移金属錯体。
- 各スペーサーが複素環をさらに有する請求項1に記載のポリマー遷移金属錯体。
- 前記スペーサーの少なくとも1個の非環状官能基が、前記スペーサーの前記複素環と前記遷移金属錯体との間に配置されている請求項9に記載のポリマー遷移金属錯体。
- 前記遷移金属錯体が下記式の構造を有する請求項1に記載のポリマー遷移金属錯体。
【化2】
[式中、
Mは、鉄、コバルト、ルテニウム、オスミウムまたはバナジウムであり、
L 1 、L 2 、L 3 、及びL 4 は含窒素複素環を有する配位子であって、L 1 、L 2 、L 3 、及びL 4 はそれぞれ独立に、一座配位子であるか、または少なくとも1個の他の配位子と組み合わさって多座配位子を形成しており、
R 1 及びR 2 は独立に、置換または未置換のアルキルであり、
R 3 、R 4 、R 5 及びR 6 は独立に、−H、−F、−Cl、−Brまたは置換もしくは未置換C1〜C12アルキルであり、
cは、正電荷または負電荷を示す−1〜−5または+1〜+5から選択される整数であり、 Xは少なくとも1個の対イオンを表し、
dは、対イオンXの数を表す1〜5の整数である]
- 前記遷移金属錯体が下記式の構造を有する請求項1に記載のポリマー遷移金属錯体。
【化3】
[式中、
Mは、鉄、コバルト、ルテニウム、オスミウムまたはバナジウムであり、
L 1 、L 2 、L 3 、及びL 4 は含窒素複素環を有する配位子であって、L 1 、L 2 、L 3 、及びL 4 はそれぞれ独立に、一座配位子であるか、または少なくとも1個の他の配位子と組み合わさって多座配位子を形成しており、
R’ 1 は、置換または未置換アルキルであり、
R’ 3 及びR’ 4 は独立に、−H、−F、−Cl、−Brまたは置換または未置換のアルキルであり、
R a 、R b 、R c 及びR d は独立に、−H、−F、−Cl、−Br、−CN、−CO 2 H、−SO 3 H、−NO 2 、−NH 2 、−NHNH 2 、−SH、または置換もしくは未置換のC1〜C12アルキルアミノ、C2〜C24ジアルキルアミノ、C1〜C12アルコキシまたはC1〜C12アルキルであり、
cは、正電荷または負電荷を示す−1〜−5または+1〜+5から選択される整数であ
り、
Xは少なくとも1個の対イオンを表し、
dは、対イオンXの数を表す1〜5の整数である]
- 前記遷移金属錯体が下記式の構造を有する請求項1に記載のポリマー遷移金属錯体。
【化4】
[式中、
Mは、鉄、コバルト、ルテニウム、オスミウムまたはバナジウムであり、
L 1 、L 2 、L 3 、及びL 4 は含窒素複素環を有する配位子であって、L 1 、L 2 、L 3 、及びL 4 はそれぞれ独立に、一座配位子であるか、または少なくとも1個の他の配位子と組み合わさって多座配位子を形成しており、
R 18 及びR 21 は独立に、−H、−F、−Cl、−Br、−CN、−CO 2 H、−OH、−SO 3 H、−NO 2 、−NH 2 、−NHNH 2 、−SH、または置換もしくは未置換のC1〜C12アルキルアミノ、C2〜C24ジアルキルアミノ、C1〜C12アルコキシまたはC1〜C12アルキルであり、
R 16 、R 17 、R 19 、R 20 、R 22 及びR 23 は独立に、−Hまたは置換もしくは未置換C1〜C12アルキルであり、
cは、正電荷または負電荷を示す−1〜−5または+1〜+5から選択される整数であり、
Xは少なくとも1個の対イオンを表し、
dは、対イオンXの数を表す1〜5の整数である]
- ポリマー遷移金属錯体において、
a)ポリマー骨格及び該ポリマー骨格から延びる複数のペンダント基を有するポリマーであって、該ペンダント基の少なくとも一部が反応性基を有するポリマーと、
b)複数の遷移金属錯体であって、各遷移金属錯体が下記式の構造を有する錯体との反応生成物を含むポリマー遷移金属錯体。
【化5】
[式中、
Mはオスミウム、ルテニウム、バナジウム、コバルトまたは鉄であり、 L 1 は、複素環を含む配位子であり、かつ該複素環のヘテロ原子を介してMに配位結合しており、
L 2 、L 3 、L 4 、L 5 及びL 6 は含窒素複素環を有する配位子であって、L 1 、L 2 、L 3 、L 4 、L 5 及びL 6 はそれぞれ独立に、一座配位子であるか、または少なくとも1個の他の配位子と組み合わさって多座配位子を形成しており、
L 1 、L 2 、L 3 、L 4 、L 5 及びL 6 のうちの少なくとも一つが、前記ポリマーの反応性基のいずれかと反応可能な反応性基を有する]
- ポリマー遷移金属錯体において、
ポリマー骨格と、
複数のスペーサーであって、各スペーサーが前記ポリマー骨格に共有結合し、その骨格から延びており、各スペーサーが少なくとも4個の原子の可撓性鎖を有するスペーサーと、
複数の遷移金属錯体であって、各遷移金属錯体が、下記式の構造を有する遷移金属錯体とを有するポリマー遷移金属錯体。
【化6】
[式中、
Mはオスミウム、ルテニウム、バナジウム、コバルトまたは鉄であり、
L 1 は、複素環を含む配位子であり、かつ該複素環のヘテロ原子を介してMに配位結合しており、
L 2 、L 3 、L 4 、L 5 及びL 6 は含窒素複素環を有する配位子であって、L 1 、L 2 、L 3 、L 4 、L 5 及びL 6 はそれぞれ独立に、一座配位子であるか、または少なくとも1個の他の配位子と組み合わさって多座配位子を形成しており、
L 1 、L 2 、L 3 、L 4 、L 5 及びL 6 のうちの少なくとも一つが、前記スペーサーのいずれかに共有結合している]
- 酸化還元メディエーターにおいて、
ポリマー骨格と、
複数のスペーサーであって、各スペーサーが前記ポリマー骨格に共有結合し、その骨格から延びており、各スペーサーが、−(CR r R s )−、−O−、−S−、−C(O)O−、−S(O) 2 NR k −、−OC(O)NR m −、−OC(S)NR n −、−C(O)NR t −、−NR u −、−CR v =N−O−、−CR w =NNR x −及び(SiR y R z )−のうちか
ら選択される少なくとも1個の非環状官能基を有し、R r 及びR s が独立に、水素、塩素、フッ素、または置換もしくは未置換のアルキル、アルコキシ、アルケニルまたはアルキニルであり、R k 、R m 、R n 、R t 、R u 、R v 、R w 、R x 、R y 及びR z が独立に、水素または置換もしくは未置換アルキルであるスペーサーと、
複数の遷移金属錯体であって、各遷移金属錯体が下記式の構造を有する遷移金属錯体とを有する酸化還元メディエーター。
【化7】
[式中、
Mはオスミウム、ルテニウム、バナジウム、コバルトまたは鉄であり、
L 1 は、複素環を含む配位子であり、かつ該複素環のヘテロ原子を介してMに配位結合しており、
L 2 、L 3 、L 4 、L 5 及びL 6 は含窒素複素環を有する配位子であって、L 1 、L 2 、L 3 、L 4 、L 5 及びL 6 はそれぞれ独立に、一座配位子であるか、または少なくとも1個の他の配位子と組み合わさって多座配位子を形成しており、
L 1 、L 2 、L 3 、L 4 、L 5 及びL 6 のうちの少なくとも一つが、前記スペーサーのいずれかに共有結合している]
- センサーにおいて、
作業電極と、
対電極と、
前記作業電極に近接して配置された酸化還元メディエーターとを有し、前記酸化還元メディエーターは、
ポリマー骨格と、
複数のスペーサーであって、各スペーサーが前記ポリマー骨格に共有結合し、その骨格から延びており、各スペーサーが、−(CR r R s )−、−O−、−S−、−C(O)O−、−S(O) 2 NR k −、−OC(O)NR m −、−OC(S)NR n −、−C(O)NR t −、−NR u −、−CR v =N−O−、−CR w =NNR x −及び(SiR y R z )−のうちから選択される少なくとも1個の非環状官能基を有し、R r 及びR s が独立に、水素、塩素、フッ素、または置換もしくは未置換のアルキル、アルコキシ、アルケニルまたはアルキニルであり、R k 、R m 、R n 、R t 、R u 、R v 、R w 、R x 、R y 及びR z が独立に、水素または置換もしくは未置換アルキルであるスペーサーと、
複数の遷移金属錯体であって、各遷移金属錯体が下記式の構造を有する遷移金属錯体とを有する、センサー。
【化8】
[式中、
Mはオスミウム、ルテニウム、バナジウム、コバルトまたは鉄であり、 L 1 は、複素環を含む配位子であり、該複素環のヘテロ原子を介してMに配位結合しており、
L 2 、L 3 、L 4 、L 5 及びL 6 は含窒素複素環を有する配位子であって、L 1 、L 2 、L 3 、L 4 、L 5 及びL 6 はそれぞれ独立に、一座配位子であるか、または少なくとも1個の他の配位子と組み合わさって多座配位子を形成しており、
L 1 、L 2 、L 3 、L 4 、L 5 及びL 6 のうちの少なくとも一つが、前記スペーサーのいずれかに共有結合している]
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US16556599P | 1999-11-15 | 1999-11-15 | |
US60/165,565 | 1999-11-15 | ||
PCT/US2000/031126 WO2001036660A2 (en) | 1999-11-15 | 2000-11-14 | Transition metal complexes attached to a polymer via a flexible chain |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2003514924A JP2003514924A (ja) | 2003-04-22 |
JP2003514924A5 JP2003514924A5 (ja) | 2008-01-10 |
JP5308609B2 true JP5308609B2 (ja) | 2013-10-09 |
Family
ID=22599460
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2001538538A Expired - Fee Related JP5308609B2 (ja) | 1999-11-15 | 2000-11-14 | ポリマー遷移金属錯体及びその用途 |
JP2001538919A Expired - Fee Related JP4932113B2 (ja) | 1999-11-15 | 2000-11-14 | イミダゾール環を有する二座配位子を含む遷移金属錯体 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2001538919A Expired - Fee Related JP4932113B2 (ja) | 1999-11-15 | 2000-11-14 | イミダゾール環を有する二座配位子を含む遷移金属錯体 |
Country Status (11)
Country | Link |
---|---|
US (11) | US6605201B1 (ja) |
EP (2) | EP1230248B1 (ja) |
JP (2) | JP5308609B2 (ja) |
AT (2) | ATE268336T1 (ja) |
AU (2) | AU1607801A (ja) |
CA (2) | CA2391423A1 (ja) |
DE (2) | DE60011286T2 (ja) |
DK (1) | DK1230249T3 (ja) |
ES (1) | ES2222252T3 (ja) |
TR (1) | TR200401326T4 (ja) |
WO (2) | WO2001036430A1 (ja) |
Families Citing this family (494)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8071384B2 (en) | 1997-12-22 | 2011-12-06 | Roche Diagnostics Operations, Inc. | Control and calibration solutions and methods for their use |
US8688188B2 (en) | 1998-04-30 | 2014-04-01 | Abbott Diabetes Care Inc. | Analyte monitoring device and methods of use |
US8465425B2 (en) | 1998-04-30 | 2013-06-18 | Abbott Diabetes Care Inc. | Analyte monitoring device and methods of use |
US8346337B2 (en) | 1998-04-30 | 2013-01-01 | Abbott Diabetes Care Inc. | Analyte monitoring device and methods of use |
US8974386B2 (en) | 1998-04-30 | 2015-03-10 | Abbott Diabetes Care Inc. | Analyte monitoring device and methods of use |
US6949816B2 (en) | 2003-04-21 | 2005-09-27 | Motorola, Inc. | Semiconductor component having first surface area for electrically coupling to a semiconductor chip and second surface area for electrically coupling to a substrate, and method of manufacturing same |
US6175752B1 (en) | 1998-04-30 | 2001-01-16 | Therasense, Inc. | Analyte monitoring device and methods of use |
US9066695B2 (en) | 1998-04-30 | 2015-06-30 | Abbott Diabetes Care Inc. | Analyte monitoring device and methods of use |
US8480580B2 (en) | 1998-04-30 | 2013-07-09 | Abbott Diabetes Care Inc. | Analyte monitoring device and methods of use |
JP4469504B2 (ja) * | 1998-10-08 | 2010-05-26 | メドトロニック ミニメド インコーポレイテッド | 遠隔形質モニタシステム |
US6338790B1 (en) | 1998-10-08 | 2002-01-15 | Therasense, Inc. | Small volume in vitro analyte sensor with diffusible or non-leachable redox mediator |
US7621893B2 (en) | 1998-10-29 | 2009-11-24 | Medtronic Minimed, Inc. | Methods and apparatuses for detecting occlusions in an ambulatory infusion pump |
US7766873B2 (en) * | 1998-10-29 | 2010-08-03 | Medtronic Minimed, Inc. | Method and apparatus for detecting occlusions in an ambulatory infusion pump |
DE19924138A1 (de) | 1999-05-26 | 2000-11-30 | Henkel Kgaa | Lösbare Klebeverbindungen |
US7806886B2 (en) | 1999-06-03 | 2010-10-05 | Medtronic Minimed, Inc. | Apparatus and method for controlling insulin infusion with state variable feedback |
US20050103624A1 (en) | 1999-10-04 | 2005-05-19 | Bhullar Raghbir S. | Biosensor and method of making |
US6355746B1 (en) * | 1999-10-06 | 2002-03-12 | Sri International | Complexes of mid-transition metals and unsaturated nitrogenous ligands as single-site catalysts |
DE19951599A1 (de) * | 1999-10-27 | 2001-05-23 | Henkel Kgaa | Verfahren zur adhesiven Trennung von Klebeverbunden |
EP1230248B1 (en) * | 1999-11-15 | 2007-06-06 | Therasense, Inc. | Transition metal complexes attached to a polymer via a flexible chain |
US8268143B2 (en) * | 1999-11-15 | 2012-09-18 | Abbott Diabetes Care Inc. | Oxygen-effect free analyte sensor |
US8444834B2 (en) | 1999-11-15 | 2013-05-21 | Abbott Diabetes Care Inc. | Redox polymers for use in analyte monitoring |
MXPA02009661A (es) | 2000-03-31 | 2004-07-30 | Lifescan Inc | Patrones electricamente conductores para verificar el llenado de dispositivos medicos.. |
DE10037884A1 (de) * | 2000-08-03 | 2002-02-21 | Henkel Kgaa | Verfahren zur beschleunigten Klebstoffaushärtung |
GB2367818A (en) * | 2000-10-11 | 2002-04-17 | Kalibrant Ltd | A linker and a method of chemical synthesis |
US6560471B1 (en) | 2001-01-02 | 2003-05-06 | Therasense, Inc. | Analyte monitoring device and methods of use |
US20050101772A1 (en) * | 2001-02-17 | 2005-05-12 | Jorg Schottek | Non-metallocenes, method for the production thereof and the use thereof for the polymerisation of olefins |
WO2002078512A2 (en) | 2001-04-02 | 2002-10-10 | Therasense, Inc. | Blood glucose tracking apparatus and methods |
US6676816B2 (en) | 2001-05-11 | 2004-01-13 | Therasense, Inc. | Transition metal complexes with (pyridyl)imidazole ligands and sensors using said complexes |
US8226814B2 (en) | 2001-05-11 | 2012-07-24 | Abbott Diabetes Care Inc. | Transition metal complexes with pyridyl-imidazole ligands |
US8070934B2 (en) | 2001-05-11 | 2011-12-06 | Abbott Diabetes Care Inc. | Transition metal complexes with (pyridyl)imidazole ligands |
US6932894B2 (en) | 2001-05-15 | 2005-08-23 | Therasense, Inc. | Biosensor membranes composed of polymers containing heterocyclic nitrogens |
US6827702B2 (en) | 2001-09-07 | 2004-12-07 | Medtronic Minimed, Inc. | Safety limits for closed-loop infusion pump control |
US7390391B2 (en) | 2001-09-14 | 2008-06-24 | Arkray, Inc. | Concentration measuring method, concentration test instrument, and concentration measuring apparatus |
US7348290B2 (en) | 2002-03-11 | 2008-03-25 | Japan Science And Technology Agency | Arene-ruthenium complexes immobilized on polymers, catalysts consisting of the complexes, and processes for organic syntheses with the same |
US7278983B2 (en) | 2002-07-24 | 2007-10-09 | Medtronic Minimed, Inc. | Physiological monitoring device for controlling a medication infusion device |
US20040068230A1 (en) * | 2002-07-24 | 2004-04-08 | Medtronic Minimed, Inc. | System for providing blood glucose measurements to an infusion device |
US8512276B2 (en) * | 2002-07-24 | 2013-08-20 | Medtronic Minimed, Inc. | System for providing blood glucose measurements to an infusion device |
US7381184B2 (en) | 2002-11-05 | 2008-06-03 | Abbott Diabetes Care Inc. | Sensor inserter assembly |
US20040122353A1 (en) * | 2002-12-19 | 2004-06-24 | Medtronic Minimed, Inc. | Relay device for transferring information between a sensor system and a fluid delivery system |
AU2003303597A1 (en) | 2002-12-31 | 2004-07-29 | Therasense, Inc. | Continuous glucose monitoring system and methods of use |
DE10310193A1 (de) * | 2003-03-06 | 2004-09-23 | Micronas Holding Gmbh | Verfahren zur Immobilisierung von Glykoproteinen |
EP1628129B1 (en) * | 2003-03-25 | 2013-12-25 | Arkray Inc. | Sensor-receiving container containing sensors |
US7741033B2 (en) * | 2003-05-13 | 2010-06-22 | Trustees Of Boston College | Electrocatalytic nucleic acid hybridization detection |
US8066639B2 (en) | 2003-06-10 | 2011-11-29 | Abbott Diabetes Care Inc. | Glucose measuring device for use in personal area network |
US7645373B2 (en) | 2003-06-20 | 2010-01-12 | Roche Diagnostic Operations, Inc. | System and method for coding information on a biosensor test strip |
US7452457B2 (en) | 2003-06-20 | 2008-11-18 | Roche Diagnostics Operations, Inc. | System and method for analyte measurement using dose sufficiency electrodes |
US7488601B2 (en) | 2003-06-20 | 2009-02-10 | Roche Diagnostic Operations, Inc. | System and method for determining an abused sensor during analyte measurement |
US8058077B2 (en) | 2003-06-20 | 2011-11-15 | Roche Diagnostics Operations, Inc. | Method for coding information on a biosensor test strip |
US8206565B2 (en) | 2003-06-20 | 2012-06-26 | Roche Diagnostics Operation, Inc. | System and method for coding information on a biosensor test strip |
US7645421B2 (en) | 2003-06-20 | 2010-01-12 | Roche Diagnostics Operations, Inc. | System and method for coding information on a biosensor test strip |
US8679853B2 (en) | 2003-06-20 | 2014-03-25 | Roche Diagnostics Operations, Inc. | Biosensor with laser-sealed capillary space and method of making |
US8071030B2 (en) | 2003-06-20 | 2011-12-06 | Roche Diagnostics Operations, Inc. | Test strip with flared sample receiving chamber |
US8148164B2 (en) | 2003-06-20 | 2012-04-03 | Roche Diagnostics Operations, Inc. | System and method for determining the concentration of an analyte in a sample fluid |
US7718439B2 (en) | 2003-06-20 | 2010-05-18 | Roche Diagnostics Operations, Inc. | System and method for coding information on a biosensor test strip |
EP1642117B1 (en) | 2003-06-20 | 2018-06-13 | Roche Diabetes Care GmbH | Reagent stripe for test strip |
US7695239B2 (en) * | 2003-07-14 | 2010-04-13 | Fortrend Engineering Corporation | End effector gripper arms having corner grippers which reorient reticle during transfer |
US8160669B2 (en) | 2003-08-01 | 2012-04-17 | Dexcom, Inc. | Transcutaneous analyte sensor |
US7774145B2 (en) | 2003-08-01 | 2010-08-10 | Dexcom, Inc. | Transcutaneous analyte sensor |
US20190357827A1 (en) | 2003-08-01 | 2019-11-28 | Dexcom, Inc. | Analyte sensor |
US7519408B2 (en) * | 2003-11-19 | 2009-04-14 | Dexcom, Inc. | Integrated receiver for continuous analyte sensor |
US7591801B2 (en) | 2004-02-26 | 2009-09-22 | Dexcom, Inc. | Integrated delivery device for continuous glucose sensor |
US8845536B2 (en) | 2003-08-01 | 2014-09-30 | Dexcom, Inc. | Transcutaneous analyte sensor |
US8275437B2 (en) | 2003-08-01 | 2012-09-25 | Dexcom, Inc. | Transcutaneous analyte sensor |
US7920906B2 (en) | 2005-03-10 | 2011-04-05 | Dexcom, Inc. | System and methods for processing analyte sensor data for sensor calibration |
US7299082B2 (en) | 2003-10-31 | 2007-11-20 | Abbott Diabetes Care, Inc. | Method of calibrating an analyte-measurement device, and associated methods, devices and systems |
USD914881S1 (en) | 2003-11-05 | 2021-03-30 | Abbott Diabetes Care Inc. | Analyte sensor electronic mount |
US9247900B2 (en) | 2004-07-13 | 2016-02-02 | Dexcom, Inc. | Analyte sensor |
US8423114B2 (en) | 2006-10-04 | 2013-04-16 | Dexcom, Inc. | Dual electrode system for a continuous analyte sensor |
US11633133B2 (en) | 2003-12-05 | 2023-04-25 | Dexcom, Inc. | Dual electrode system for a continuous analyte sensor |
EP2239566B1 (en) | 2003-12-05 | 2014-04-23 | DexCom, Inc. | Calibration techniques for a continuous analyte sensor |
EP3263032B1 (en) | 2003-12-09 | 2024-01-24 | Dexcom, Inc. | Signal processing for continuous analyte sensor |
US8063216B2 (en) | 2003-12-29 | 2011-11-22 | The Trustees Of Columbia University In The City Of New York | Photolabile compounds |
EP1713926B1 (en) | 2004-02-06 | 2012-08-01 | Bayer HealthCare, LLC | Oxidizable species as an internal reference for biosensors and method of use |
US8165651B2 (en) | 2004-02-09 | 2012-04-24 | Abbott Diabetes Care Inc. | Analyte sensor, and associated system and method employing a catalytic agent |
US7699964B2 (en) | 2004-02-09 | 2010-04-20 | Abbott Diabetes Care Inc. | Membrane suitable for use in an analyte sensor, analyte sensor, and associated method |
WO2005089103A2 (en) | 2004-02-17 | 2005-09-29 | Therasense, Inc. | Method and system for providing data communication in continuous glucose monitoring and management system |
US8808228B2 (en) | 2004-02-26 | 2014-08-19 | Dexcom, Inc. | Integrated medicament delivery device for use with continuous analyte sensor |
WO2009048462A1 (en) | 2007-10-09 | 2009-04-16 | Dexcom, Inc. | Integrated insulin delivery system with continuous glucose sensor |
JP2007534961A (ja) * | 2004-04-29 | 2007-11-29 | エイジェンシー・フォー・サイエンス,テクノロジー・アンド・リサーチ | 核酸および/またはポリペプチドを検出するための方法および装置 |
WO2006093505A2 (en) * | 2004-05-10 | 2006-09-08 | Northwestern University | Compositions and methods for analyte detection |
CA2566358C (en) | 2004-05-21 | 2016-12-20 | Agamatrix, Inc. | Electrochemical cell and method for making an electrochemical cell |
CA2572455C (en) | 2004-06-04 | 2014-10-28 | Therasense, Inc. | Diabetes care host-client architecture and data management system |
US20070100222A1 (en) * | 2004-06-14 | 2007-05-03 | Metronic Minimed, Inc. | Analyte sensing apparatus for hospital use |
US7569126B2 (en) | 2004-06-18 | 2009-08-04 | Roche Diagnostics Operations, Inc. | System and method for quality assurance of a biosensor test strip |
US7640048B2 (en) | 2004-07-13 | 2009-12-29 | Dexcom, Inc. | Analyte sensor |
US7654956B2 (en) | 2004-07-13 | 2010-02-02 | Dexcom, Inc. | Transcutaneous analyte sensor |
US8565848B2 (en) | 2004-07-13 | 2013-10-22 | Dexcom, Inc. | Transcutaneous analyte sensor |
US8452368B2 (en) | 2004-07-13 | 2013-05-28 | Dexcom, Inc. | Transcutaneous analyte sensor |
US7344500B2 (en) | 2004-07-27 | 2008-03-18 | Medtronic Minimed, Inc. | Sensing system with auxiliary display |
US7511142B2 (en) * | 2004-07-28 | 2009-03-31 | Agency For Science, Technology And Research | Mediator-modified redox biomolecules for use in electrochemical determination of analyte |
US7109271B2 (en) * | 2004-07-28 | 2006-09-19 | Lifescan, Inc. | Redox polymers for use in electrochemical-based sensors |
US7303543B1 (en) | 2004-12-03 | 2007-12-04 | Medtronic Minimed, Inc. | Medication infusion set |
US7331174B2 (en) * | 2004-12-16 | 2008-02-19 | Independent Natural Resources, Inc. | Buoyancy pump power system |
US10226207B2 (en) | 2004-12-29 | 2019-03-12 | Abbott Diabetes Care Inc. | Sensor inserter having introducer |
US9572534B2 (en) | 2010-06-29 | 2017-02-21 | Abbott Diabetes Care Inc. | Devices, systems and methods for on-skin or on-body mounting of medical devices |
US9636450B2 (en) | 2007-02-19 | 2017-05-02 | Udo Hoss | Pump system modular components for delivering medication and analyte sensing at seperate insertion sites |
US8333714B2 (en) | 2006-09-10 | 2012-12-18 | Abbott Diabetes Care Inc. | Method and system for providing an integrated analyte sensor insertion device and data processing unit |
US7697967B2 (en) | 2005-12-28 | 2010-04-13 | Abbott Diabetes Care Inc. | Method and apparatus for providing analyte sensor insertion |
US8029441B2 (en) | 2006-02-28 | 2011-10-04 | Abbott Diabetes Care Inc. | Analyte sensor transmitter unit configuration for a data monitoring and management system |
US9398882B2 (en) | 2005-09-30 | 2016-07-26 | Abbott Diabetes Care Inc. | Method and apparatus for providing analyte sensor and data processing device |
US9351669B2 (en) | 2009-09-30 | 2016-05-31 | Abbott Diabetes Care Inc. | Interconnect for on-body analyte monitoring device |
US9743862B2 (en) | 2011-03-31 | 2017-08-29 | Abbott Diabetes Care Inc. | Systems and methods for transcutaneously implanting medical devices |
US8512243B2 (en) | 2005-09-30 | 2013-08-20 | Abbott Diabetes Care Inc. | Integrated introducer and transmitter assembly and methods of use |
US7883464B2 (en) | 2005-09-30 | 2011-02-08 | Abbott Diabetes Care Inc. | Integrated transmitter unit and sensor introducer mechanism and methods of use |
US7731657B2 (en) | 2005-08-30 | 2010-06-08 | Abbott Diabetes Care Inc. | Analyte sensor introducer and methods of use |
US20090105569A1 (en) | 2006-04-28 | 2009-04-23 | Abbott Diabetes Care, Inc. | Introducer Assembly and Methods of Use |
US8571624B2 (en) | 2004-12-29 | 2013-10-29 | Abbott Diabetes Care Inc. | Method and apparatus for mounting a data transmission device in a communication system |
US9259175B2 (en) | 2006-10-23 | 2016-02-16 | Abbott Diabetes Care, Inc. | Flexible patch for fluid delivery and monitoring body analytes |
US9788771B2 (en) | 2006-10-23 | 2017-10-17 | Abbott Diabetes Care Inc. | Variable speed sensor insertion devices and methods of use |
US7704229B2 (en) | 2005-02-03 | 2010-04-27 | Medtronic Minimed, Inc. | Insertion device |
US20060184104A1 (en) * | 2005-02-15 | 2006-08-17 | Medtronic Minimed, Inc. | Needle guard |
TWI259019B (en) * | 2005-03-23 | 2006-07-21 | Au Optronics Corp | Organometallic compound and organic light-emitting diode and display including the organometallic compound |
US7465380B2 (en) * | 2005-04-12 | 2008-12-16 | Lifescan Scotland, Ltd. | Water-miscible conductive ink for use in enzymatic electrochemical-based sensors |
WO2007094805A2 (en) * | 2005-04-12 | 2007-08-23 | The Trustees Of Boston College | Method for electrocatalytic protein detection |
US8112240B2 (en) | 2005-04-29 | 2012-02-07 | Abbott Diabetes Care Inc. | Method and apparatus for providing leak detection in data monitoring and management systems |
US20070033074A1 (en) * | 2005-06-03 | 2007-02-08 | Medtronic Minimed, Inc. | Therapy management system |
US20060272652A1 (en) * | 2005-06-03 | 2006-12-07 | Medtronic Minimed, Inc. | Virtual patient software system for educating and treating individuals with diabetes |
US20070016449A1 (en) * | 2005-06-29 | 2007-01-18 | Gary Cohen | Flexible glucose analysis using varying time report deltas and configurable glucose target ranges |
EP1904508B1 (en) * | 2005-06-30 | 2009-08-12 | Koninklijke Philips Electronics N.V. | Electro luminescent metal complexes |
CA2890945C (en) | 2005-07-20 | 2016-11-29 | Bayer Healthcare Llc | Gated amperometry |
US20070066956A1 (en) * | 2005-07-27 | 2007-03-22 | Medtronic Minimed, Inc. | Systems and methods for entering temporary basal rate pattern in an infusion device |
US7737581B2 (en) | 2005-08-16 | 2010-06-15 | Medtronic Minimed, Inc. | Method and apparatus for predicting end of battery life |
US20090227855A1 (en) | 2005-08-16 | 2009-09-10 | Medtronic Minimed, Inc. | Controller device for an infusion pump |
US20070060870A1 (en) * | 2005-08-16 | 2007-03-15 | Tolle Mike Charles V | Controller device for an infusion pump |
US20070093786A1 (en) * | 2005-08-16 | 2007-04-26 | Medtronic Minimed, Inc. | Watch controller for a medical device |
US20080314395A1 (en) | 2005-08-31 | 2008-12-25 | Theuniversity Of Virginia Patent Foundation | Accuracy of Continuous Glucose Sensors |
US7713240B2 (en) | 2005-09-13 | 2010-05-11 | Medtronic Minimed, Inc. | Modular external infusion device |
US9072476B2 (en) | 2005-09-23 | 2015-07-07 | Medtronic Minimed, Inc. | Flexible sensor apparatus |
US7725148B2 (en) * | 2005-09-23 | 2010-05-25 | Medtronic Minimed, Inc. | Sensor with layered electrodes |
US8880138B2 (en) | 2005-09-30 | 2014-11-04 | Abbott Diabetes Care Inc. | Device for channeling fluid and methods of use |
US9521968B2 (en) | 2005-09-30 | 2016-12-20 | Abbott Diabetes Care Inc. | Analyte sensor retention mechanism and methods of use |
AU2006297572B2 (en) | 2005-09-30 | 2012-11-15 | Ascensia Diabetes Care Holdings Ag | Gated Voltammetry |
US7766829B2 (en) | 2005-11-04 | 2010-08-03 | Abbott Diabetes Care Inc. | Method and system for providing basal profile modification in analyte monitoring and management systems |
US7918975B2 (en) | 2005-11-17 | 2011-04-05 | Abbott Diabetes Care Inc. | Analytical sensors for biological fluid |
US7955484B2 (en) * | 2005-12-14 | 2011-06-07 | Nova Biomedical Corporation | Glucose biosensor and method |
EP1968432A4 (en) | 2005-12-28 | 2009-10-21 | Abbott Diabetes Care Inc | INTRODUCTION OF A MEDICAL DEVICE |
US11298058B2 (en) | 2005-12-28 | 2022-04-12 | Abbott Diabetes Care Inc. | Method and apparatus for providing analyte sensor insertion |
US8515518B2 (en) | 2005-12-28 | 2013-08-20 | Abbott Diabetes Care Inc. | Analyte monitoring |
US8160670B2 (en) * | 2005-12-28 | 2012-04-17 | Abbott Diabetes Care Inc. | Analyte monitoring: stabilizer for subcutaneous glucose sensor with incorporated antiglycolytic agent |
US7774038B2 (en) * | 2005-12-30 | 2010-08-10 | Medtronic Minimed, Inc. | Real-time self-calibrating sensor system and method |
US8114269B2 (en) | 2005-12-30 | 2012-02-14 | Medtronic Minimed, Inc. | System and method for determining the point of hydration and proper time to apply potential to a glucose sensor |
US8114268B2 (en) | 2005-12-30 | 2012-02-14 | Medtronic Minimed, Inc. | Method and system for remedying sensor malfunctions detected by electrochemical impedance spectroscopy |
US20070173712A1 (en) | 2005-12-30 | 2007-07-26 | Medtronic Minimed, Inc. | Method of and system for stabilization of sensors |
US7985330B2 (en) * | 2005-12-30 | 2011-07-26 | Medtronic Minimed, Inc. | Method and system for detecting age, hydration, and functional states of sensors using electrochemical impedance spectroscopy |
US20070169533A1 (en) | 2005-12-30 | 2007-07-26 | Medtronic Minimed, Inc. | Methods and systems for detecting the hydration of sensors |
US7736310B2 (en) | 2006-01-30 | 2010-06-15 | Abbott Diabetes Care Inc. | On-body medical device securement |
US7826879B2 (en) | 2006-02-28 | 2010-11-02 | Abbott Diabetes Care Inc. | Analyte sensors and methods of use |
US7885698B2 (en) | 2006-02-28 | 2011-02-08 | Abbott Diabetes Care Inc. | Method and system for providing continuous calibration of implantable analyte sensors |
DE102006014715B3 (de) * | 2006-03-30 | 2007-06-06 | Drägerwerk AG | Elektrochemischer Sensor aufweisend eine Mediator-Verbindung mit einem Festkörper |
DE102006014714B3 (de) * | 2006-03-30 | 2007-05-16 | Draegerwerk Ag | Elektrochemischer Sensor aufweisend eine Mediator-Verbindung |
US9392969B2 (en) | 2008-08-31 | 2016-07-19 | Abbott Diabetes Care Inc. | Closed loop control and signal attenuation detection |
US8473022B2 (en) | 2008-01-31 | 2013-06-25 | Abbott Diabetes Care Inc. | Analyte sensor with time lag compensation |
US9339217B2 (en) | 2011-11-25 | 2016-05-17 | Abbott Diabetes Care Inc. | Analyte monitoring system and methods of use |
US8226891B2 (en) | 2006-03-31 | 2012-07-24 | Abbott Diabetes Care Inc. | Analyte monitoring devices and methods therefor |
US8478557B2 (en) | 2009-07-31 | 2013-07-02 | Abbott Diabetes Care Inc. | Method and apparatus for providing analyte monitoring system calibration accuracy |
US7630748B2 (en) | 2006-10-25 | 2009-12-08 | Abbott Diabetes Care Inc. | Method and system for providing analyte monitoring |
US7653425B2 (en) | 2006-08-09 | 2010-01-26 | Abbott Diabetes Care Inc. | Method and system for providing calibration of an analyte sensor in an analyte monitoring system |
US9326709B2 (en) | 2010-03-10 | 2016-05-03 | Abbott Diabetes Care Inc. | Systems, devices and methods for managing glucose levels |
US7618369B2 (en) | 2006-10-02 | 2009-11-17 | Abbott Diabetes Care Inc. | Method and system for dynamically updating calibration parameters for an analyte sensor |
US7620438B2 (en) | 2006-03-31 | 2009-11-17 | Abbott Diabetes Care Inc. | Method and system for powering an electronic device |
US8374668B1 (en) | 2007-10-23 | 2013-02-12 | Abbott Diabetes Care Inc. | Analyte sensor with lag compensation |
US7801582B2 (en) | 2006-03-31 | 2010-09-21 | Abbott Diabetes Care Inc. | Analyte monitoring and management system and methods therefor |
US8140312B2 (en) | 2007-05-14 | 2012-03-20 | Abbott Diabetes Care Inc. | Method and system for determining analyte levels |
US9675290B2 (en) | 2012-10-30 | 2017-06-13 | Abbott Diabetes Care Inc. | Sensitivity calibration of in vivo sensors used to measure analyte concentration |
US8219173B2 (en) | 2008-09-30 | 2012-07-10 | Abbott Diabetes Care Inc. | Optimizing analyte sensor calibration |
US8224415B2 (en) | 2009-01-29 | 2012-07-17 | Abbott Diabetes Care Inc. | Method and device for providing offset model based calibration for analyte sensor |
US8346335B2 (en) | 2008-03-28 | 2013-01-01 | Abbott Diabetes Care Inc. | Analyte sensor calibration management |
US7942844B2 (en) | 2006-04-28 | 2011-05-17 | Medtronic Minimed, Inc. | Remote monitoring for networked fluid infusion systems |
US8073008B2 (en) | 2006-04-28 | 2011-12-06 | Medtronic Minimed, Inc. | Subnetwork synchronization and variable transmit synchronization techniques for a wireless medical device network |
US20080064937A1 (en) | 2006-06-07 | 2008-03-13 | Abbott Diabetes Care, Inc. | Analyte monitoring system and method |
WO2008007277A2 (en) * | 2006-06-27 | 2008-01-17 | Agamatrix, Inc. | Detection of analytes in a dual-mediator electrochemical test strip |
US7866026B1 (en) * | 2006-08-01 | 2011-01-11 | Abbott Diabetes Care Inc. | Method for making calibration-adjusted sensors |
US8618032B2 (en) * | 2006-09-22 | 2013-12-31 | Terumo Kabushiki Kaisha | Polymer having visibility in magnetic resonance image and surface lubricity and medical device |
EP2083674B1 (en) | 2006-10-24 | 2018-03-07 | Ascensia Diabetes Care Holdings AG | Transient decay amperometry |
BRPI0718119A2 (pt) | 2006-10-26 | 2014-07-08 | Abbott Diabetes Care Inc | Métodos, sistemas e programas de computador para a detecção em tempo real do declínio de sensibilidade em sensores de analito |
US20080139910A1 (en) * | 2006-12-06 | 2008-06-12 | Metronic Minimed, Inc. | Analyte sensor and method of using the same |
US7802467B2 (en) | 2006-12-22 | 2010-09-28 | Abbott Diabetes Care Inc. | Analyte sensors and methods of use |
US10154804B2 (en) | 2007-01-31 | 2018-12-18 | Medtronic Minimed, Inc. | Model predictive method and system for controlling and supervising insulin infusion |
US8121857B2 (en) | 2007-02-15 | 2012-02-21 | Abbott Diabetes Care Inc. | Device and method for automatic data acquisition and/or detection |
US20080199894A1 (en) | 2007-02-15 | 2008-08-21 | Abbott Diabetes Care, Inc. | Device and method for automatic data acquisition and/or detection |
US8930203B2 (en) | 2007-02-18 | 2015-01-06 | Abbott Diabetes Care Inc. | Multi-function analyte test device and methods therefor |
US8732188B2 (en) | 2007-02-18 | 2014-05-20 | Abbott Diabetes Care Inc. | Method and system for providing contextual based medication dosage determination |
US8123686B2 (en) | 2007-03-01 | 2012-02-28 | Abbott Diabetes Care Inc. | Method and apparatus for providing rolling data in communication systems |
CA2683930A1 (en) | 2007-04-14 | 2008-10-23 | Abbott Diabetes Care Inc. | Method and apparatus for providing data processing and control in medical communication system |
EP2146622B1 (en) | 2007-04-14 | 2016-05-11 | Abbott Diabetes Care Inc. | Method and apparatus for providing dynamic multi-stage signal amplification in a medical device |
US9008743B2 (en) | 2007-04-14 | 2015-04-14 | Abbott Diabetes Care Inc. | Method and apparatus for providing data processing and control in medical communication system |
WO2009096992A1 (en) | 2007-04-14 | 2009-08-06 | Abbott Diabetes Care, Inc. | Method and apparatus for providing data processing and control in medical communication system |
ES2784736T3 (es) | 2007-04-14 | 2020-09-30 | Abbott Diabetes Care Inc | Procedimiento y aparato para proporcionar el procesamiento y control de datos en un sistema de comunicación médica |
WO2008130896A1 (en) | 2007-04-14 | 2008-10-30 | Abbott Diabetes Care, Inc. | Method and apparatus for providing data processing and control in medical communication system |
US20080269714A1 (en) | 2007-04-25 | 2008-10-30 | Medtronic Minimed, Inc. | Closed loop/semi-closed loop therapy modification system |
US8665091B2 (en) | 2007-05-08 | 2014-03-04 | Abbott Diabetes Care Inc. | Method and device for determining elapsed sensor life |
US7928850B2 (en) | 2007-05-08 | 2011-04-19 | Abbott Diabetes Care Inc. | Analyte monitoring system and methods |
US8461985B2 (en) | 2007-05-08 | 2013-06-11 | Abbott Diabetes Care Inc. | Analyte monitoring system and methods |
US8456301B2 (en) | 2007-05-08 | 2013-06-04 | Abbott Diabetes Care Inc. | Analyte monitoring system and methods |
US8560038B2 (en) | 2007-05-14 | 2013-10-15 | Abbott Diabetes Care Inc. | Method and apparatus for providing data processing and control in a medical communication system |
US7996158B2 (en) | 2007-05-14 | 2011-08-09 | Abbott Diabetes Care Inc. | Method and apparatus for providing data processing and control in a medical communication system |
US8444560B2 (en) | 2007-05-14 | 2013-05-21 | Abbott Diabetes Care Inc. | Method and apparatus for providing data processing and control in a medical communication system |
US8103471B2 (en) | 2007-05-14 | 2012-01-24 | Abbott Diabetes Care Inc. | Method and apparatus for providing data processing and control in a medical communication system |
US8600681B2 (en) | 2007-05-14 | 2013-12-03 | Abbott Diabetes Care Inc. | Method and apparatus for providing data processing and control in a medical communication system |
US8239166B2 (en) | 2007-05-14 | 2012-08-07 | Abbott Diabetes Care Inc. | Method and apparatus for providing data processing and control in a medical communication system |
US8260558B2 (en) | 2007-05-14 | 2012-09-04 | Abbott Diabetes Care Inc. | Method and apparatus for providing data processing and control in a medical communication system |
US9125548B2 (en) | 2007-05-14 | 2015-09-08 | Abbott Diabetes Care Inc. | Method and apparatus for providing data processing and control in a medical communication system |
US10002233B2 (en) | 2007-05-14 | 2018-06-19 | Abbott Diabetes Care Inc. | Method and apparatus for providing data processing and control in a medical communication system |
WO2008150917A1 (en) | 2007-05-31 | 2008-12-11 | Abbott Diabetes Care, Inc. | Insertion devices and methods |
US8562558B2 (en) | 2007-06-08 | 2013-10-22 | Dexcom, Inc. | Integrated medicament delivery device for use with continuous analyte sensor |
GB0711849D0 (en) * | 2007-06-19 | 2007-07-25 | Oxford Biosensors Ltd | Redox Mediators |
WO2008157821A1 (en) | 2007-06-21 | 2008-12-24 | Abbott Diabetes Care, Inc. | Health monitor |
WO2008157820A1 (en) | 2007-06-21 | 2008-12-24 | Abbott Diabetes Care, Inc. | Health management devices and methods |
US8160900B2 (en) | 2007-06-29 | 2012-04-17 | Abbott Diabetes Care Inc. | Analyte monitoring and management device and method to analyze the frequency of user interaction with the device |
US7768386B2 (en) | 2007-07-31 | 2010-08-03 | Abbott Diabetes Care Inc. | Method and apparatus for providing data processing and control in a medical communication system |
US8834366B2 (en) | 2007-07-31 | 2014-09-16 | Abbott Diabetes Care Inc. | Method and apparatus for providing analyte sensor calibration |
US8409093B2 (en) | 2007-10-23 | 2013-04-02 | Abbott Diabetes Care Inc. | Assessing measures of glycemic variability |
US8377031B2 (en) | 2007-10-23 | 2013-02-19 | Abbott Diabetes Care Inc. | Closed loop control system with safety parameters and methods |
US8216138B1 (en) | 2007-10-23 | 2012-07-10 | Abbott Diabetes Care Inc. | Correlation of alternative site blood and interstitial fluid glucose concentrations to venous glucose concentration |
WO2009076302A1 (en) | 2007-12-10 | 2009-06-18 | Bayer Healthcare Llc | Control markers for auto-detection of control solution and methods of use |
US20090164239A1 (en) | 2007-12-19 | 2009-06-25 | Abbott Diabetes Care, Inc. | Dynamic Display Of Glucose Information |
US8313467B2 (en) | 2007-12-27 | 2012-11-20 | Medtronic Minimed, Inc. | Reservoir pressure equalization systems and methods |
CA2715628A1 (en) | 2008-02-21 | 2009-08-27 | Dexcom, Inc. | Systems and methods for processing, transmitting and displaying sensor data |
US20090259118A1 (en) * | 2008-03-31 | 2009-10-15 | Abbott Diabetes Care Inc. | Shallow Implantable Analyte Sensor with Rapid Physiological Response |
US8241616B2 (en) * | 2008-04-03 | 2012-08-14 | Rohm And Haas Company | Hair styling composition |
EP3659628A1 (en) | 2008-04-10 | 2020-06-03 | Abbott Diabetes Care, Inc. | Method and system for sterilizing an analyte sensor |
US8262874B2 (en) | 2008-04-14 | 2012-09-11 | Abbott Diabetes Care Inc. | Biosensor coating composition and methods thereof |
US9295786B2 (en) | 2008-05-28 | 2016-03-29 | Medtronic Minimed, Inc. | Needle protective device for subcutaneous sensors |
US8591410B2 (en) | 2008-05-30 | 2013-11-26 | Abbott Diabetes Care Inc. | Method and apparatus for providing glycemic control |
US7826382B2 (en) | 2008-05-30 | 2010-11-02 | Abbott Diabetes Care Inc. | Close proximity communication device and methods |
US8924159B2 (en) | 2008-05-30 | 2014-12-30 | Abbott Diabetes Care Inc. | Method and apparatus for providing glycemic control |
US20090294307A1 (en) * | 2008-06-02 | 2009-12-03 | Zenghe Liu | Redox polymer based reference electrodes having an extended lifetime for use in long term amperometric sensors |
WO2010009172A1 (en) | 2008-07-14 | 2010-01-21 | Abbott Diabetes Care Inc. | Closed loop control system interface and methods |
US20100030052A1 (en) * | 2008-07-31 | 2010-02-04 | Bommakanti Balasubrahmanya S | Analyte sensors comprising plasticizers |
US9943644B2 (en) | 2008-08-31 | 2018-04-17 | Abbott Diabetes Care Inc. | Closed loop control with reference measurement and methods thereof |
US8734422B2 (en) | 2008-08-31 | 2014-05-27 | Abbott Diabetes Care Inc. | Closed loop control with improved alarm functions |
US8622988B2 (en) | 2008-08-31 | 2014-01-07 | Abbott Diabetes Care Inc. | Variable rate closed loop control and methods |
US20100057040A1 (en) | 2008-08-31 | 2010-03-04 | Abbott Diabetes Care, Inc. | Robust Closed Loop Control And Methods |
US8637194B2 (en) | 2008-09-02 | 2014-01-28 | Bio-Nano Power, Llc | Bio-nano power cells and their uses |
ES2732948T3 (es) | 2008-09-02 | 2019-11-26 | Governing Council Univ Toronto | Métodos que utilizan microelectrodos y dispositivos biosensores que incorporan los mismos |
US8636884B2 (en) * | 2008-09-15 | 2014-01-28 | Abbott Diabetes Care Inc. | Cationic polymer based wired enzyme formulations for use in analyte sensors |
US8986208B2 (en) | 2008-09-30 | 2015-03-24 | Abbott Diabetes Care Inc. | Analyte sensor sensitivity attenuation mitigation |
US8983568B2 (en) | 2008-09-30 | 2015-03-17 | Abbott Diabetes Care Inc. | Analyte sensors comprising leveling agents |
US8208973B2 (en) | 2008-11-05 | 2012-06-26 | Medtronic Minimed, Inc. | System and method for variable beacon timing with wireless devices |
US9326707B2 (en) | 2008-11-10 | 2016-05-03 | Abbott Diabetes Care Inc. | Alarm characterization for analyte monitoring devices and systems |
US9330237B2 (en) | 2008-12-24 | 2016-05-03 | Medtronic Minimed, Inc. | Pattern recognition and filtering in a therapy management system |
KR101048980B1 (ko) * | 2009-01-16 | 2011-07-12 | 삼성모바일디스플레이주식회사 | 터치 스크린 패널 및 그 제조방법 |
US8103456B2 (en) | 2009-01-29 | 2012-01-24 | Abbott Diabetes Care Inc. | Method and device for early signal attenuation detection using blood glucose measurements |
US20100198034A1 (en) | 2009-02-03 | 2010-08-05 | Abbott Diabetes Care Inc. | Compact On-Body Physiological Monitoring Devices and Methods Thereof |
WO2011034629A1 (en) * | 2009-02-05 | 2011-03-24 | Abbott Diabetes Care Inc. | Devices and methods for metering insoluble active agent particles |
EP3912551B1 (en) | 2009-02-26 | 2023-08-30 | Abbott Diabetes Care, Inc. | Method of calibrating an analyte sensor |
WO2010121084A1 (en) | 2009-04-15 | 2010-10-21 | Abbott Diabetes Care Inc. | Analyte monitoring system having an alert |
WO2010121229A1 (en) | 2009-04-16 | 2010-10-21 | Abbott Diabetes Care Inc. | Analyte sensor calibration management |
WO2010127050A1 (en) | 2009-04-28 | 2010-11-04 | Abbott Diabetes Care Inc. | Error detection in critical repeating data in a wireless sensor system |
EP2425209A4 (en) | 2009-04-29 | 2013-01-09 | Abbott Diabetes Care Inc | METHOD AND SYSTEM FOR REAL-TIME CALIBRATION OF AN ANALYTICAL SENSOR WITH RETROACTIVE FILLING |
US8368556B2 (en) | 2009-04-29 | 2013-02-05 | Abbott Diabetes Care Inc. | Method and system for providing data communication in continuous glucose monitoring and management system |
US9184490B2 (en) | 2009-05-29 | 2015-11-10 | Abbott Diabetes Care Inc. | Medical device antenna systems having external antenna configurations |
US8283347B2 (en) * | 2009-06-01 | 2012-10-09 | Bayer Healthcare Llc | Redox molecules and methods of making the same |
EP2438527B1 (en) | 2009-06-04 | 2018-05-02 | Abbott Diabetes Care, Inc. | Method and system for updating a medical device |
US8437827B2 (en) * | 2009-06-30 | 2013-05-07 | Abbott Diabetes Care Inc. | Extruded analyte sensors and methods of using same |
US8613892B2 (en) | 2009-06-30 | 2013-12-24 | Abbott Diabetes Care Inc. | Analyte meter with a moveable head and methods of using the same |
US20100331643A1 (en) * | 2009-06-30 | 2010-12-30 | Abbott Diabetes Care Inc. | Extruded Analyte Sensors and Methods of Using Same |
US8344847B2 (en) | 2009-07-09 | 2013-01-01 | Medtronic Minimed, Inc. | Coordination of control commands in a medical device system having at least one therapy delivery device and at least one wireless controller device |
ES2884623T3 (es) | 2009-07-23 | 2021-12-10 | Abbott Diabetes Care Inc | Procedimiento de fabricación y sistema de medición continua de analitos |
US20110040208A1 (en) * | 2009-08-11 | 2011-02-17 | Abbott Diabetes Care Inc. | Integrated lancet and test strip and methods of making and using same |
US20110046466A1 (en) * | 2009-08-19 | 2011-02-24 | Feldman Benjamin J | Analyte Sensors Including Nanomaterials and Methods of Using Same |
CA2765712A1 (en) | 2009-08-31 | 2011-03-03 | Abbott Diabetes Care Inc. | Medical devices and methods |
EP4070729B1 (en) | 2009-08-31 | 2024-05-01 | Abbott Diabetes Care, Inc. | Displays for a medical device |
US8993331B2 (en) | 2009-08-31 | 2015-03-31 | Abbott Diabetes Care Inc. | Analyte monitoring system and methods for managing power and noise |
WO2011026147A1 (en) | 2009-08-31 | 2011-03-03 | Abbott Diabetes Care Inc. | Analyte signal processing device and methods |
US8487758B2 (en) | 2009-09-02 | 2013-07-16 | Medtronic Minimed, Inc. | Medical device having an intelligent alerting scheme, and related operating methods |
EP2482720A4 (en) | 2009-09-29 | 2014-04-23 | Abbott Diabetes Care Inc | METHOD AND APPARATUS FOR PROVIDING NOTIFICATION FUNCTION IN SUBSTANCE MONITORING SYSTEMS |
EP2494323A4 (en) | 2009-10-30 | 2014-07-16 | Abbott Diabetes Care Inc | METHOD AND DEVICE FOR DETECTING UNNORMAL HYPOGLYKEMIC VALUES |
US8386042B2 (en) | 2009-11-03 | 2013-02-26 | Medtronic Minimed, Inc. | Omnidirectional accelerometer device and medical device incorporating same |
US9042954B2 (en) * | 2009-11-24 | 2015-05-26 | Abbott Diabetes Care Inc. | Analyte sensors comprising hydrogel membranes |
US8354013B2 (en) | 2009-11-24 | 2013-01-15 | Abbott Diabetes Care Inc. | Analyte sensors comprising high-boiling point solvents |
US20110124993A1 (en) * | 2009-11-24 | 2011-05-26 | Abbott Diabetes Care Inc. | Analyte Sensors Comprising Self-Polymerizing Hydrogels |
US9354226B2 (en) | 2009-12-17 | 2016-05-31 | Ascensia Diabetes Care Holdings Ag | Transdermal systems, devices, and methods to optically analyze an analyte |
US8574201B2 (en) | 2009-12-22 | 2013-11-05 | Medtronic Minimed, Inc. | Syringe piston with check valve seal |
US8755269B2 (en) | 2009-12-23 | 2014-06-17 | Medtronic Minimed, Inc. | Ranking and switching of wireless channels in a body area network of medical devices |
USD924406S1 (en) | 2010-02-01 | 2021-07-06 | Abbott Diabetes Care Inc. | Analyte sensor inserter |
KR101100987B1 (ko) * | 2010-03-23 | 2011-12-30 | 삼성모바일디스플레이주식회사 | 터치 스크린 패널 |
LT3622883T (lt) | 2010-03-24 | 2021-08-25 | Abbott Diabetes Care, Inc. | Medicinos prietaiso įvedikliai ir medicinos prietaisų įvedimo ir naudojimo būdai |
CN102469941B (zh) | 2010-04-16 | 2016-04-13 | 艾伯特糖尿病护理公司 | 分析物监视设备和方法 |
US8726266B2 (en) | 2010-05-24 | 2014-05-13 | Abbott Diabetes Care Inc. | Method and system for updating a medical device |
WO2011150155A1 (en) | 2010-05-28 | 2011-12-01 | Bayer Healthcare Llc | Polymer bonded redox molecules and methods of making the same |
US8635046B2 (en) | 2010-06-23 | 2014-01-21 | Abbott Diabetes Care Inc. | Method and system for evaluating analyte sensor response characteristics |
US11064921B2 (en) | 2010-06-29 | 2021-07-20 | Abbott Diabetes Care Inc. | Devices, systems and methods for on-skin or on-body mounting of medical devices |
US10092229B2 (en) | 2010-06-29 | 2018-10-09 | Abbott Diabetes Care Inc. | Calibration of analyte measurement system |
US9085790B2 (en) | 2010-07-28 | 2015-07-21 | Abbott Diabetes Care Inc. | Analyte sensors having temperature independent membranes |
US11213226B2 (en) | 2010-10-07 | 2022-01-04 | Abbott Diabetes Care Inc. | Analyte monitoring devices and methods |
US8562565B2 (en) | 2010-10-15 | 2013-10-22 | Medtronic Minimed, Inc. | Battery shock absorber for a portable medical device |
US8603033B2 (en) | 2010-10-15 | 2013-12-10 | Medtronic Minimed, Inc. | Medical device and related assembly having an offset element for a piezoelectric speaker |
US8603032B2 (en) | 2010-10-15 | 2013-12-10 | Medtronic Minimed, Inc. | Medical device with membrane keypad sealing element, and related manufacturing method |
US8479595B2 (en) | 2010-10-20 | 2013-07-09 | Medtronic Minimed, Inc. | Sensor assembly and medical device incorporating same |
US8495918B2 (en) | 2010-10-20 | 2013-07-30 | Medtronic Minimed, Inc. | Sensor assembly and medical device incorporating same |
US8474332B2 (en) | 2010-10-20 | 2013-07-02 | Medtronic Minimed, Inc. | Sensor assembly and medical device incorporating same |
WO2012078908A1 (en) | 2010-12-09 | 2012-06-14 | Abbott Diabetes Care Inc. | Analyte sensors with a sensing surface having small sensing spots |
US8469942B2 (en) | 2010-12-22 | 2013-06-25 | Medtronic Minimed, Inc. | Occlusion detection for a fluid infusion device |
US8690855B2 (en) * | 2010-12-22 | 2014-04-08 | Medtronic Minimed, Inc. | Fluid reservoir seating procedure for a fluid infusion device |
US8197444B1 (en) | 2010-12-22 | 2012-06-12 | Medtronic Minimed, Inc. | Monitoring the seating status of a fluid reservoir in a fluid infusion device |
US8628510B2 (en) | 2010-12-22 | 2014-01-14 | Medtronic Minimed, Inc. | Monitoring the operating health of a force sensor in a fluid infusion device |
US9772329B2 (en) | 2011-01-11 | 2017-09-26 | The Governing Council Of The University Of Toronto | Protein detection method |
WO2012108936A1 (en) | 2011-02-11 | 2012-08-16 | Abbott Diabetes Care Inc. | Data synchronization between two or more analyte detecting devices in a database |
WO2012108938A1 (en) | 2011-02-11 | 2012-08-16 | Abbott Diabetes Care Inc. | Software applications residing on handheld analyte determining devices |
WO2012108939A1 (en) | 2011-02-11 | 2012-08-16 | Abbott Diabetes Care Inc. | Feedback from cloud or hcp to payer or patient via meter or cell phone |
US9283318B2 (en) | 2011-02-22 | 2016-03-15 | Medtronic Minimed, Inc. | Flanged sealing element and needle guide pin assembly for a fluid infusion device having a needled fluid reservoir |
US9393399B2 (en) | 2011-02-22 | 2016-07-19 | Medtronic Minimed, Inc. | Sealing assembly for a fluid reservoir of a fluid infusion device |
US8864726B2 (en) | 2011-02-22 | 2014-10-21 | Medtronic Minimed, Inc. | Pressure vented fluid reservoir having a movable septum |
US9463309B2 (en) | 2011-02-22 | 2016-10-11 | Medtronic Minimed, Inc. | Sealing assembly and structure for a fluid infusion device having a needled fluid reservoir |
US10136845B2 (en) | 2011-02-28 | 2018-11-27 | Abbott Diabetes Care Inc. | Devices, systems, and methods associated with analyte monitoring devices and devices incorporating the same |
US8614596B2 (en) | 2011-02-28 | 2013-12-24 | Medtronic Minimed, Inc. | Systems and methods for initializing a voltage bus and medical devices incorporating same |
EP3583901A3 (en) | 2011-02-28 | 2020-01-15 | Abbott Diabetes Care, Inc. | Devices, systems, and methods associated with analyte monitoring devices and devices incorporating the same |
US9101305B2 (en) | 2011-03-09 | 2015-08-11 | Medtronic Minimed, Inc. | Glucose sensor product and related manufacturing and packaging methods |
US9580742B2 (en) | 2011-03-10 | 2017-02-28 | Shana O. Kelley | Diagnostic and sample preparation devices and methods |
US9018893B2 (en) | 2011-03-18 | 2015-04-28 | Medtronic Minimed, Inc. | Power control techniques for an electronic device |
US8564447B2 (en) | 2011-03-18 | 2013-10-22 | Medtronic Minimed, Inc. | Battery life indication techniques for an electronic device |
EP2697650B1 (en) | 2011-04-15 | 2020-09-30 | Dexcom, Inc. | Advanced analyte sensor calibration and error detection |
US9380965B2 (en) | 2011-05-20 | 2016-07-05 | Abbott Diabetes Care Inc. | Analyte sensors having a membrane with low temperature sensitivity |
EP2737078B1 (en) | 2011-07-27 | 2017-11-01 | Agamatrix, Inc. | Reagents for electrochemical test strips |
EP3381360A1 (en) | 2011-09-28 | 2018-10-03 | Abbott Diabetes Care, Inc. | Methods, devices and systems for analyte monitoring management |
JP2013081410A (ja) | 2011-10-07 | 2013-05-09 | Toyota Motor Corp | 変異型マルチ銅オキシダーゼ、これをコードする遺伝子及びこれを用いたバイオ燃料電池 |
US9622691B2 (en) | 2011-10-31 | 2017-04-18 | Abbott Diabetes Care Inc. | Model based variable risk false glucose threshold alarm prevention mechanism |
WO2013066873A1 (en) | 2011-10-31 | 2013-05-10 | Abbott Diabetes Care Inc. | Electronic devices having integrated reset systems and methods thereof |
JP6443802B2 (ja) | 2011-11-07 | 2018-12-26 | アボット ダイアベティス ケア インコーポレイテッドAbbott Diabetes Care Inc. | 分析物モニタリング装置および方法 |
US8710993B2 (en) | 2011-11-23 | 2014-04-29 | Abbott Diabetes Care Inc. | Mitigating single point failure of devices in an analyte monitoring system and methods thereof |
US9317656B2 (en) | 2011-11-23 | 2016-04-19 | Abbott Diabetes Care Inc. | Compatibility mechanisms for devices in a continuous analyte monitoring system and methods thereof |
DK4056105T3 (da) | 2011-12-11 | 2024-01-02 | Abbott Diabetes Care Inc | Analytsensorindretninger |
US9610401B2 (en) | 2012-01-13 | 2017-04-04 | Medtronic Minimed, Inc. | Infusion set component with modular fluid channel element |
US8523803B1 (en) | 2012-03-20 | 2013-09-03 | Medtronic Minimed, Inc. | Motor health monitoring and medical device incorporating same |
US8603026B2 (en) | 2012-03-20 | 2013-12-10 | Medtronic Minimed, Inc. | Dynamic pulse-width modulation motor control and medical device incorporating same |
US8603027B2 (en) | 2012-03-20 | 2013-12-10 | Medtronic Minimed, Inc. | Occlusion detection using pulse-width modulation and medical device incorporating same |
US9462970B2 (en) | 2012-04-24 | 2016-10-11 | Abbott Diabetes Care Inc. | Methods of lag-compensation for analyte measurements, and devices related thereto |
US10391242B2 (en) | 2012-06-07 | 2019-08-27 | Medtronic Minimed, Inc. | Diabetes therapy management system for recommending bolus calculator adjustments |
US9333292B2 (en) | 2012-06-26 | 2016-05-10 | Medtronic Minimed, Inc. | Mechanically actuated fluid infusion device |
US8808269B2 (en) | 2012-08-21 | 2014-08-19 | Medtronic Minimed, Inc. | Reservoir plunger position monitoring and medical device incorporating same |
US9623179B2 (en) | 2012-08-30 | 2017-04-18 | Medtronic Minimed, Inc. | Safeguarding techniques for a closed-loop insulin infusion system |
US9364609B2 (en) | 2012-08-30 | 2016-06-14 | Medtronic Minimed, Inc. | Insulin on board compensation for a closed-loop insulin infusion system |
US10130767B2 (en) | 2012-08-30 | 2018-11-20 | Medtronic Minimed, Inc. | Sensor model supervisor for a closed-loop insulin infusion system |
US9662445B2 (en) | 2012-08-30 | 2017-05-30 | Medtronic Minimed, Inc. | Regulating entry into a closed-loop operating mode of an insulin infusion system |
US9878096B2 (en) | 2012-08-30 | 2018-01-30 | Medtronic Minimed, Inc. | Generation of target glucose values for a closed-loop operating mode of an insulin infusion system |
JP6052768B2 (ja) * | 2012-08-30 | 2016-12-27 | 国立大学法人静岡大学 | 陰イオン交換体 |
EP2890297B1 (en) | 2012-08-30 | 2018-04-11 | Abbott Diabetes Care, Inc. | Dropout detection in continuous analyte monitoring data during data excursions |
US9849239B2 (en) | 2012-08-30 | 2017-12-26 | Medtronic Minimed, Inc. | Generation and application of an insulin limit for a closed-loop operating mode of an insulin infusion system |
US10496797B2 (en) | 2012-08-30 | 2019-12-03 | Medtronic Minimed, Inc. | Blood glucose validation for a closed-loop operating mode of an insulin infusion system |
US9968306B2 (en) | 2012-09-17 | 2018-05-15 | Abbott Diabetes Care Inc. | Methods and apparatuses for providing adverse condition notification with enhanced wireless communication range in analyte monitoring systems |
US10006880B2 (en) | 2012-09-21 | 2018-06-26 | Abbott Diabetes Care Inc. | Test strips having ceria nanoparticle electrodes |
EP2901153A4 (en) | 2012-09-26 | 2016-04-27 | Abbott Diabetes Care Inc | METHOD AND DEVICE FOR IMPROVING DELAY CORRECTION FUNCTION DURING IN VIVO MEASUREMENT OF ANALYZ CONCENTRATION WITH ANALYZ CONCENTRATION VARIABILITY AND RANGE DATA |
US9272769B2 (en) * | 2012-11-13 | 2016-03-01 | The Boeing Company | Joint for composite wings |
US8870818B2 (en) | 2012-11-15 | 2014-10-28 | Medtronic Minimed, Inc. | Systems and methods for alignment and detection of a consumable component |
WO2014099907A1 (en) | 2012-12-18 | 2014-06-26 | Abbott Diabetes Care Inc. | Dermal layer analyte sensing devices and methods |
US9522223B2 (en) | 2013-01-18 | 2016-12-20 | Medtronic Minimed, Inc. | Systems for fluid reservoir retention |
US9033924B2 (en) | 2013-01-18 | 2015-05-19 | Medtronic Minimed, Inc. | Systems for fluid reservoir retention |
US9107994B2 (en) | 2013-01-18 | 2015-08-18 | Medtronic Minimed, Inc. | Systems for fluid reservoir retention |
US9308321B2 (en) | 2013-02-18 | 2016-04-12 | Medtronic Minimed, Inc. | Infusion device having gear assembly initialization |
US9474475B1 (en) | 2013-03-15 | 2016-10-25 | Abbott Diabetes Care Inc. | Multi-rate analyte sensor data collection with sample rate configurable signal processing |
WO2014152034A1 (en) | 2013-03-15 | 2014-09-25 | Abbott Diabetes Care Inc. | Sensor fault detection using analyte sensor data pattern comparison |
US10433773B1 (en) | 2013-03-15 | 2019-10-08 | Abbott Diabetes Care Inc. | Noise rejection methods and apparatus for sparsely sampled analyte sensor data |
US8920381B2 (en) | 2013-04-12 | 2014-12-30 | Medtronic Minimed, Inc. | Infusion set with improved bore configuration |
CA2909552A1 (en) | 2013-04-30 | 2014-11-06 | Abbott Diabetes Care Inc. | Systems, devices, and methods for energy efficient electrical device activation |
US9433731B2 (en) | 2013-07-19 | 2016-09-06 | Medtronic Minimed, Inc. | Detecting unintentional motor motion and infusion device incorporating same |
US9402949B2 (en) | 2013-08-13 | 2016-08-02 | Medtronic Minimed, Inc. | Detecting conditions associated with medical device operations using matched filters |
US9880528B2 (en) | 2013-08-21 | 2018-01-30 | Medtronic Minimed, Inc. | Medical devices and related updating methods and systems |
US9889257B2 (en) | 2013-08-21 | 2018-02-13 | Medtronic Minimed, Inc. | Systems and methods for updating medical devices |
US9259528B2 (en) | 2013-08-22 | 2016-02-16 | Medtronic Minimed, Inc. | Fluid infusion device with safety coupling |
US9306179B2 (en) * | 2013-11-08 | 2016-04-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9750877B2 (en) | 2013-12-11 | 2017-09-05 | Medtronic Minimed, Inc. | Predicted time to assess and/or control a glycemic state |
US9750878B2 (en) | 2013-12-11 | 2017-09-05 | Medtronic Minimed, Inc. | Closed-loop control of glucose according to a predicted blood glucose trajectory |
US10105488B2 (en) | 2013-12-12 | 2018-10-23 | Medtronic Minimed, Inc. | Predictive infusion device operations and related methods and systems |
US9849240B2 (en) | 2013-12-12 | 2017-12-26 | Medtronic Minimed, Inc. | Data modification for predictive operations and devices incorporating same |
US9694132B2 (en) | 2013-12-19 | 2017-07-04 | Medtronic Minimed, Inc. | Insertion device for insertion set |
RU2683203C2 (ru) | 2013-12-31 | 2019-03-26 | Эбботт Дайабитиз Кэр Инк. | Снабженный автономным питанием датчик аналита и использующие его устройства |
US9399096B2 (en) | 2014-02-06 | 2016-07-26 | Medtronic Minimed, Inc. | Automatic closed-loop control adjustments and infusion systems incorporating same |
US9861748B2 (en) | 2014-02-06 | 2018-01-09 | Medtronic Minimed, Inc. | User-configurable closed-loop notifications and infusion systems incorporating same |
US9610402B2 (en) | 2014-03-24 | 2017-04-04 | Medtronic Minimed, Inc. | Transcutaneous conduit insertion mechanism with a living hinge for use with a fluid infusion patch pump device |
WO2015153482A1 (en) | 2014-03-30 | 2015-10-08 | Abbott Diabetes Care Inc. | Method and apparatus for determining meal start and peak events in analyte monitoring systems |
US10001450B2 (en) | 2014-04-18 | 2018-06-19 | Medtronic Minimed, Inc. | Nonlinear mapping technique for a physiological characteristic sensor |
US10232113B2 (en) | 2014-04-24 | 2019-03-19 | Medtronic Minimed, Inc. | Infusion devices and related methods and systems for regulating insulin on board |
US9681828B2 (en) | 2014-05-01 | 2017-06-20 | Medtronic Minimed, Inc. | Physiological characteristic sensors and methods for forming such sensors |
US10275572B2 (en) | 2014-05-01 | 2019-04-30 | Medtronic Minimed, Inc. | Detecting blockage of a reservoir cavity during a seating operation of a fluid infusion device |
US10152049B2 (en) | 2014-05-19 | 2018-12-11 | Medtronic Minimed, Inc. | Glucose sensor health monitoring and related methods and systems |
US10274349B2 (en) | 2014-05-19 | 2019-04-30 | Medtronic Minimed, Inc. | Calibration factor adjustments for infusion devices and related methods and systems |
US10007765B2 (en) | 2014-05-19 | 2018-06-26 | Medtronic Minimed, Inc. | Adaptive signal processing for infusion devices and related methods and systems |
AU2015302326A1 (en) | 2014-08-15 | 2017-03-02 | Abbott Diabetes Care Inc. | Temperature insensitive in vivo analyte devices, methods and systems |
US9839753B2 (en) | 2014-09-26 | 2017-12-12 | Medtronic Minimed, Inc. | Systems for managing reservoir chamber pressure |
US9833563B2 (en) | 2014-09-26 | 2017-12-05 | Medtronic Minimed, Inc. | Systems for managing reservoir chamber pressure |
US10279126B2 (en) | 2014-10-07 | 2019-05-07 | Medtronic Minimed, Inc. | Fluid conduit assembly with gas trapping filter in the fluid flow path |
WO2016065190A1 (en) | 2014-10-23 | 2016-04-28 | Abbott Diabetes Care Inc. | Electrodes having at least one sensing structure and methods for making and using the same |
US9833564B2 (en) | 2014-11-25 | 2017-12-05 | Medtronic Minimed, Inc. | Fluid conduit assembly with air venting features |
US10195341B2 (en) | 2014-11-26 | 2019-02-05 | Medtronic Minimed, Inc. | Systems and methods for fluid infusion device with automatic reservoir fill |
US9987420B2 (en) | 2014-11-26 | 2018-06-05 | Medtronic Minimed, Inc. | Systems and methods for fluid infusion device with automatic reservoir fill |
US9943645B2 (en) | 2014-12-04 | 2018-04-17 | Medtronic Minimed, Inc. | Methods for operating mode transitions and related infusion devices and systems |
US9636453B2 (en) | 2014-12-04 | 2017-05-02 | Medtronic Minimed, Inc. | Advance diagnosis of infusion device operating mode viability |
US9937292B2 (en) | 2014-12-09 | 2018-04-10 | Medtronic Minimed, Inc. | Systems for filling a fluid infusion device reservoir |
US10307535B2 (en) | 2014-12-19 | 2019-06-04 | Medtronic Minimed, Inc. | Infusion devices and related methods and systems for preemptive alerting |
US10265031B2 (en) | 2014-12-19 | 2019-04-23 | Medtronic Minimed, Inc. | Infusion devices and related methods and systems for automatic alert clearing |
US10307528B2 (en) | 2015-03-09 | 2019-06-04 | Medtronic Minimed, Inc. | Extensible infusion devices and related methods |
US10449298B2 (en) | 2015-03-26 | 2019-10-22 | Medtronic Minimed, Inc. | Fluid injection devices and related methods |
US10213139B2 (en) | 2015-05-14 | 2019-02-26 | Abbott Diabetes Care Inc. | Systems, devices, and methods for assembling an applicator and sensor control device |
EP3294134B1 (en) | 2015-05-14 | 2020-07-08 | Abbott Diabetes Care Inc. | Inserter system for a compact medical device and corresponding method |
US10137243B2 (en) | 2015-05-26 | 2018-11-27 | Medtronic Minimed, Inc. | Infusion devices with distributed motor control and related operating methods |
US9999721B2 (en) | 2015-05-26 | 2018-06-19 | Medtronic Minimed, Inc. | Error handling in infusion devices with distributed motor control and related operating methods |
US10575767B2 (en) | 2015-05-29 | 2020-03-03 | Medtronic Minimed, Inc. | Method for monitoring an analyte, analyte sensor and analyte monitoring apparatus |
CN107735027A (zh) | 2015-06-15 | 2018-02-23 | 雅培糖尿病护理股份有限公司 | 稳定的乳酸响应酶、电极和传感器以及制备和使用它们的方法 |
US9878095B2 (en) | 2015-06-22 | 2018-01-30 | Medtronic Minimed, Inc. | Occlusion detection techniques for a fluid infusion device having a rotary pump mechanism and multiple sensor contact elements |
US9993594B2 (en) | 2015-06-22 | 2018-06-12 | Medtronic Minimed, Inc. | Occlusion detection techniques for a fluid infusion device having a rotary pump mechanism and rotor position sensors |
US9879668B2 (en) | 2015-06-22 | 2018-01-30 | Medtronic Minimed, Inc. | Occlusion detection techniques for a fluid infusion device having a rotary pump mechanism and an optical sensor |
US10010668B2 (en) | 2015-06-22 | 2018-07-03 | Medtronic Minimed, Inc. | Occlusion detection techniques for a fluid infusion device having a rotary pump mechanism and a force sensor |
US9987425B2 (en) | 2015-06-22 | 2018-06-05 | Medtronic Minimed, Inc. | Occlusion detection techniques for a fluid infusion device having a rotary pump mechanism and sensor contact elements |
CA2991716A1 (en) | 2015-07-10 | 2017-01-19 | Abbott Diabetes Care Inc. | System, device and method of dynamic glucose profile response to physiological parameters |
US10888272B2 (en) | 2015-07-10 | 2021-01-12 | Abbott Diabetes Care Inc. | Systems, devices, and methods for meal information collection, meal assessment, and analyte data correlation |
US10293108B2 (en) | 2015-08-21 | 2019-05-21 | Medtronic Minimed, Inc. | Infusion devices and related patient ratio adjustment methods |
US10463297B2 (en) | 2015-08-21 | 2019-11-05 | Medtronic Minimed, Inc. | Personalized event detection methods and related devices and systems |
US10543314B2 (en) | 2015-08-21 | 2020-01-28 | Medtronic Minimed, Inc. | Personalized parameter modeling with signal calibration based on historical data |
US10201657B2 (en) | 2015-08-21 | 2019-02-12 | Medtronic Minimed, Inc. | Methods for providing sensor site rotation feedback and related infusion devices and systems |
US10867012B2 (en) | 2015-08-21 | 2020-12-15 | Medtronic Minimed, Inc. | Data analytics and insight delivery for the management and control of diabetes |
US10117992B2 (en) | 2015-09-29 | 2018-11-06 | Medtronic Minimed, Inc. | Infusion devices and related rescue detection methods |
US11666702B2 (en) | 2015-10-19 | 2023-06-06 | Medtronic Minimed, Inc. | Medical devices and related event pattern treatment recommendation methods |
US11501867B2 (en) | 2015-10-19 | 2022-11-15 | Medtronic Minimed, Inc. | Medical devices and related event pattern presentation methods |
US10146911B2 (en) | 2015-10-23 | 2018-12-04 | Medtronic Minimed, Inc. | Medical devices and related methods and systems for data transfer |
US10037722B2 (en) | 2015-11-03 | 2018-07-31 | Medtronic Minimed, Inc. | Detecting breakage in a display element |
US10449306B2 (en) | 2015-11-25 | 2019-10-22 | Medtronics Minimed, Inc. | Systems for fluid delivery with wicking membrane |
US10202327B2 (en) * | 2016-02-02 | 2019-02-12 | University Of Southern California | Highly robust efficient catalyst for selective dehydrogenation of neat glycerol to lactic acid |
US11091788B2 (en) | 2016-03-04 | 2021-08-17 | Abbott Diabetes Care Inc. | NAD(P)- dependent responsive enzymes, electrodes and sensors, and methods for making and using the same |
US10589038B2 (en) | 2016-04-27 | 2020-03-17 | Medtronic Minimed, Inc. | Set connector systems for venting a fluid reservoir |
US11097051B2 (en) | 2016-11-04 | 2021-08-24 | Medtronic Minimed, Inc. | Methods and apparatus for detecting and reacting to insufficient hypoglycemia response |
US10238030B2 (en) | 2016-12-06 | 2019-03-26 | Medtronic Minimed, Inc. | Wireless medical device with a complementary split ring resonator arrangement for suppression of electromagnetic interference |
US10272201B2 (en) | 2016-12-22 | 2019-04-30 | Medtronic Minimed, Inc. | Insertion site monitoring methods and related infusion devices and systems |
CA3050721A1 (en) | 2017-01-23 | 2018-07-26 | Abbott Diabetes Care Inc. | Systems, devices and methods for analyte sensor insertion |
US10532165B2 (en) | 2017-01-30 | 2020-01-14 | Medtronic Minimed, Inc. | Fluid reservoir and systems for filling a fluid reservoir of a fluid infusion device |
US10500135B2 (en) | 2017-01-30 | 2019-12-10 | Medtronic Minimed, Inc. | Fluid reservoir and systems for filling a fluid reservoir of a fluid infusion device |
US10363365B2 (en) | 2017-02-07 | 2019-07-30 | Medtronic Minimed, Inc. | Infusion devices and related consumable calibration methods |
US10552580B2 (en) | 2017-02-07 | 2020-02-04 | Medtronic Minimed, Inc. | Infusion system consumables and related calibration methods |
US11207463B2 (en) | 2017-02-21 | 2021-12-28 | Medtronic Minimed, Inc. | Apparatuses, systems, and methods for identifying an infusate in a reservoir of an infusion device |
US10646649B2 (en) | 2017-02-21 | 2020-05-12 | Medtronic Minimed, Inc. | Infusion devices and fluid identification apparatuses and methods |
EP3600014A4 (en) | 2017-03-21 | 2020-10-21 | Abbott Diabetes Care Inc. | METHODS, DEVICES AND SYSTEM FOR PROVIDING DIAGNOSIS AND THERAPY FOR DIABETIC CONDITION |
EP3645733B1 (en) | 2017-06-30 | 2023-04-26 | Abbott Diabetes Care | Method and apparatus for analyte detection using an electrochemical biosensor |
US11331022B2 (en) | 2017-10-24 | 2022-05-17 | Dexcom, Inc. | Pre-connected analyte sensors |
US20190120785A1 (en) | 2017-10-24 | 2019-04-25 | Dexcom, Inc. | Pre-connected analyte sensors |
WO2019089476A1 (en) | 2017-10-30 | 2019-05-09 | Abbott Diabetes Care Inc. | Transcutaneous sensor with dual electrodes and methods of detecting and compensating for withdrawal of a transcutaneous sensor from a patient |
TWI762731B (zh) * | 2017-11-08 | 2022-05-01 | 美商羅門哈斯電子材料有限公司 | 銅電鍍組合物及在基板上電鍍銅之方法 |
US20190320947A1 (en) | 2018-04-19 | 2019-10-24 | Abbott Diabetes Care Inc. | Lactate sensors and associated methods |
KR102352758B1 (ko) * | 2018-04-23 | 2022-01-18 | 주식회사 아이센스 | 신규한 전이금속 복합체를 포함하는 산화-환원 고분자 및 이를 이용한 전기화학적 바이오센서 |
US20210236028A1 (en) | 2018-05-17 | 2021-08-05 | Abbott Diabetes Care Inc. | Analyte sensor antimicrobial configurations and adhesives |
MX2021002015A (es) | 2018-08-23 | 2021-04-28 | Abbott Diabetes Care Inc | Sensores y metodos para medir el ph. |
EP3854827B1 (en) * | 2018-09-18 | 2023-11-08 | i-Sens, Inc. | Oxidation-reduction polymer including transition metal complex, and electrochemical biosensor using same |
WO2020060194A1 (ko) * | 2018-09-18 | 2020-03-26 | 주식회사 아이센스 | 폴리알릴글라이시딜에터 기반의 산화-환원 고분자 및 이를 이용한 전기화학적 바이오센서 |
TWI819180B (zh) * | 2019-01-17 | 2023-10-21 | 荷蘭商Asm 智慧財產控股公司 | 藉由循環沈積製程於基板上形成含過渡金屬膜之方法 |
EP3917394B1 (en) | 2019-01-28 | 2024-08-14 | Abbott Diabetes Care Inc. | Analyte sensors employing multiple enzymes |
WO2020159584A1 (en) | 2019-01-28 | 2020-08-06 | Abbott Diabetes Care Inc. | Analyte sensors and sensing methods for detecting creatinine |
US20200237277A1 (en) | 2019-01-28 | 2020-07-30 | Abbott Diabetes Care Inc. | Analyte sensors and sensing methods for dual detection of glucose and ethanol |
EP3917396A1 (en) | 2019-01-28 | 2021-12-08 | Abbott Diabetes Care Inc. | Analyte sensors and sensing methods featuring dual detection of glucose and ketones |
USD1002852S1 (en) | 2019-06-06 | 2023-10-24 | Abbott Diabetes Care Inc. | Analyte sensor device |
AU2020337996C1 (en) | 2019-08-30 | 2024-05-02 | Abbott Diabetes Care Inc. | Analyte sensors and sensing methods for the detection of alcohol |
US20220322978A1 (en) | 2019-09-30 | 2022-10-13 | Phc Holdings Corporation | High molecular weight redox polymer and biosensor using same |
US20220372542A1 (en) | 2019-10-02 | 2022-11-24 | Abbott Diabetes Care Inc. | Detection of analytes by protein switches |
CN114981649A (zh) | 2019-12-23 | 2022-08-30 | 美国雅培糖尿病护理公司 | 特征是低电位检测的分析物传感器和传感方法 |
WO2021138473A1 (en) | 2020-01-03 | 2021-07-08 | Abbott Diabetes Care Inc. | Sensor array systems and methods for detecting multiple analytes |
WO2021221752A2 (en) | 2020-02-06 | 2021-11-04 | Trustees Of Boston University | High throughput assay for identifying microbial redox enzymes |
US11331020B2 (en) | 2020-02-06 | 2022-05-17 | Trustees Of Boston University | Enzyme-based electrochemical nicotine biosensor |
TW202203850A (zh) | 2020-03-13 | 2022-02-01 | 瑞士商赫孚孟拉羅股份公司 | 製備工作電極的方法 |
CN115768349A (zh) | 2020-05-29 | 2023-03-07 | 美国雅培糖尿病护理公司 | 用于检测黄递酶抑制剂的分析物传感器和传感方法 |
JP2023530631A (ja) | 2020-06-10 | 2023-07-19 | アボット ダイアベティス ケア インコーポレイテッド | 一つ以上の検出促進強化を備える被検物質センサ |
AU2021306551A1 (en) | 2020-07-07 | 2022-12-08 | F. Hoffmann-La Roche Ag | Analyte sensor and its manufacturing |
USD957438S1 (en) | 2020-07-29 | 2022-07-12 | Abbott Diabetes Care Inc. | Display screen or portion thereof with graphical user interface |
CN112067671B (zh) * | 2020-08-18 | 2022-09-23 | 微泰医疗器械(杭州)股份有限公司 | 一种葡萄糖电化学传感器及其制备方法 |
AU2021379053A1 (en) | 2020-11-12 | 2023-02-23 | F. Hoffmann-La Roche Ag | Method for manufacturing at least one electrode of an analyte sensor |
KR20230106671A (ko) | 2020-11-20 | 2023-07-13 | 에프. 호프만-라 로슈 아게 | 플럭스 제한 중합체 막 |
EP4248201A1 (en) | 2020-11-23 | 2023-09-27 | F. Hoffmann-La Roche AG | Method for preparing a working electrode |
EP4000517A1 (en) | 2020-11-23 | 2022-05-25 | Roche Diabetes Care GmbH | Working electrode for an analyte sensor |
IL302960A (en) | 2020-11-24 | 2023-07-01 | Hoffmann La Roche | Method for preparing a counter/reference electrode |
AU2021395004A1 (en) | 2020-12-10 | 2023-06-22 | Abbott Diabetes Care Inc. | Analyte sensors for sensing ketones and methods of using the same |
JP2023554367A (ja) | 2020-12-15 | 2023-12-27 | アボット ダイアベティス ケア インコーポレイテッド | Nad(p)依存性酵素ベースのセンサのためのnad(p)デポー |
USD999913S1 (en) | 2020-12-21 | 2023-09-26 | Abbott Diabetes Care Inc | Analyte sensor inserter |
EP4267752A1 (en) | 2020-12-23 | 2023-11-01 | Abbott Diabetes Care, Inc. | Analyte sensors for sensing glutamate and methods of using the same |
US20220192548A1 (en) | 2020-12-23 | 2022-06-23 | Abbott Diabetes Care Inc. | Continuous Potassium Sensors and Methods of Use Thereof |
CN117098852A (zh) | 2020-12-30 | 2023-11-21 | 美国雅培糖尿病护理公司 | 用于检测天冬酰胺和天冬氨酸的分析物传感器及其使用方法 |
CN116997293A (zh) | 2020-12-31 | 2023-11-03 | 雅培糖尿病护理公司 | 用于紧邻分析物传感器输送治疗剂的分析物传感器和尖锐件及其方法 |
WO2022147496A1 (en) | 2020-12-31 | 2022-07-07 | Abbott Diabetes Care Inc. | Analyte sensors with metal-containing redox mediators and methods of using the same |
WO2022147506A1 (en) | 2020-12-31 | 2022-07-07 | Abbott Diabetes Care Inc. | Analyte sensors and methods of use thereof |
JP2024504174A (ja) | 2021-01-26 | 2024-01-30 | アボット ダイアベティス ケア インコーポレイテッド | ケトンセンサに関連するシステム、デバイス、および方法 |
EP4130729A1 (en) | 2021-08-04 | 2023-02-08 | Roche Diabetes Care GmbH | Opening formation in a membrane of a biosensor |
WO2022232670A1 (en) | 2021-04-30 | 2022-11-03 | Trustees Of Boston University | Hormone electrochemical biosensor |
WO2023283096A1 (en) | 2021-07-06 | 2023-01-12 | Roche Diabetes Care, Inc. | Analyte sensor and method for manufacturing an analyte sensor |
EP4115806A1 (en) | 2021-07-06 | 2023-01-11 | Roche Diabetes Care GmbH | Analyte sensor and method for manufacturing an analyte sensor |
EP4134004A1 (en) | 2021-08-11 | 2023-02-15 | Roche Diabetes Care GmbH | Regulation of a two-electrode analyte sensor |
EP4140408B1 (en) | 2021-08-30 | 2024-08-21 | Roche Diabetes Care GmbH | Membrane with biodegradable polymer |
EP4151151A1 (en) | 2021-09-21 | 2023-03-22 | F. Hoffmann-La Roche AG | Sensor with varying stiffness |
WO2023110190A1 (en) | 2021-12-13 | 2023-06-22 | Heraeus Medical Gmbh | Tests and methods for detecting bacterial infection |
KR20240122778A (ko) | 2021-12-24 | 2024-08-13 | 에프. 호프만-라 로슈 아게 | 분석물 센서 및 분석물 센서를 제조하기 위한 방법 |
EP4212095A1 (en) | 2022-01-18 | 2023-07-19 | F. Hoffmann-La Roche AG | Analyte sensor and method for manufacturing an analyte sensor |
EP4230129A1 (en) | 2022-02-22 | 2023-08-23 | Roche Diabetes Care GmbH | Safety unit for analyte sensor |
DE102022000897A1 (de) | 2022-03-15 | 2023-09-21 | Ruhr-Universität Bochum, Körperschaft des öffentlichen Rechts | Implantierbarer Biosensor |
EP4278966A1 (en) | 2022-05-16 | 2023-11-22 | Roche Diabetes Care GmbH | Analyte sensor morphology |
US20240027390A1 (en) | 2022-07-19 | 2024-01-25 | Abbott Diabetes Care Inc. | Analyte sensors with reduced interferent signal and methods |
EP4357778A1 (en) | 2022-10-20 | 2024-04-24 | Heraeus Medical GmbH | Treatment of microbial infections diagnosed using the biomarker d-lactate |
US20240240159A1 (en) | 2022-11-28 | 2024-07-18 | Abbott Diabetes Care, Inc | Universal sensing system |
US20240216589A1 (en) | 2022-12-30 | 2024-07-04 | Abbott Diabetis Care Inc. | Drug delivery compositions and methods of controlling drug delivery rates of subcutaneous sensors |
US20240272113A1 (en) | 2023-01-25 | 2024-08-15 | Abbott Diabetes Care Inc. | Temperature-insensitive membranes for analyte sensors |
Family Cites Families (43)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS533788B2 (ja) * | 1974-03-13 | 1978-02-09 | ||
JPS52105988A (en) * | 1976-03-03 | 1977-09-06 | Hidetoshi Tsuchida | Polymer containing nicotinamide radical of oxidized and rediced types* and highhpolymeric metal complex containing such polymer |
US5682884A (en) * | 1983-05-05 | 1997-11-04 | Medisense, Inc. | Strip electrode with screen printing |
JPH01114012A (ja) | 1987-10-28 | 1989-05-02 | Hitachi Ltd | 内周巻線らせん組込装置 |
US5262035A (en) | 1989-08-02 | 1993-11-16 | E. Heller And Company | Enzyme electrodes |
US5264104A (en) | 1989-08-02 | 1993-11-23 | Gregg Brian A | Enzyme electrodes |
US5320725A (en) | 1989-08-02 | 1994-06-14 | E. Heller & Company | Electrode and method for the detection of hydrogen peroxide |
US5264105A (en) | 1989-08-02 | 1993-11-23 | Gregg Brian A | Enzyme electrodes |
JP2971927B2 (ja) * | 1990-09-04 | 1999-11-08 | 汪芳 白井 | テルピリジル基を担持した親水性ポリマーおよびこれを配位した高分子錯体 |
FR2673183B1 (fr) | 1991-02-21 | 1996-09-27 | Asulab Sa | Complexes mono, bis ou tris (2,2'-bipyridine substituee) d'un metal choisi parmi le fer, le ruthenium, l'osmium ou le vanadium et leurs procedes de preparation . |
FR2673289B1 (fr) | 1991-02-21 | 1994-06-17 | Asulab Sa | Capteur de mesure de la quantite d'un composant en solution. |
US5262305A (en) | 1991-03-04 | 1993-11-16 | E. Heller & Company | Interferant eliminating biosensors |
JPH04278450A (ja) | 1991-03-04 | 1992-10-05 | Adam Heller | バイオセンサー及び分析物を分析する方法 |
US5593852A (en) | 1993-12-02 | 1997-01-14 | Heller; Adam | Subcutaneous glucose electrode |
US5264092A (en) * | 1991-10-02 | 1993-11-23 | Moltech Corporation | Redox polymer modified electrode for the electrochemical regeneration of coenzyme |
GB9217811D0 (en) * | 1992-08-21 | 1992-10-07 | Graetzel Michael | Organic compounds |
FR2699170B1 (fr) | 1992-12-15 | 1995-07-28 | Asulab Sa | Complexes d'un métal de transition à ligands 2,2'-bipyridine substitués par au moins un radical ammonium alkyle, leur procédé de fabrication et leur application comme médiateur redox. |
US5804049A (en) * | 1993-09-15 | 1998-09-08 | Chiron Diagnostics Corporation | Material for establishing solid state contact for ion selective electrodes |
US5589326A (en) | 1993-12-30 | 1996-12-31 | Boehringer Mannheim Corporation | Osmium-containing redox mediator |
US5437999A (en) | 1994-02-22 | 1995-08-01 | Boehringer Mannheim Corporation | Electrochemical sensor |
EP0758337B1 (en) * | 1994-05-02 | 1998-12-16 | Ecole Polytechnique Federale De Lausanne | Phosphonated polypyridyl compounds and their complexes |
ES2244958T3 (es) * | 1994-12-21 | 2005-12-16 | Hydro Quebec | Sales hidrofobicas liquidas, su prepracion y su aplicacion en electroquimica. |
US5972199A (en) | 1995-10-11 | 1999-10-26 | E. Heller & Company | Electrochemical analyte sensors using thermostable peroxidase |
US5665222A (en) | 1995-10-11 | 1997-09-09 | E. Heller & Company | Soybean peroxidase electrochemical sensor |
US6297062B1 (en) * | 1996-03-07 | 2001-10-02 | Bio-Magnetics Ltd. | Separation by magnetic particles |
DE69809391T2 (de) | 1997-02-06 | 2003-07-10 | Therasense, Inc. | Kleinvolumiger sensor zur in-vitro bestimmung |
DE69819712T2 (de) * | 1997-05-07 | 2004-09-23 | Ecole polytechnique fédérale de Lausanne (EPFL) | Fotoempfindlicher metallkomplex und fotovoltaische zelle |
GB9714905D0 (en) | 1997-07-16 | 1997-09-17 | Johnson Matthey Plc | Photosensitizers |
US6103033A (en) | 1998-03-04 | 2000-08-15 | Therasense, Inc. | Process for producing an electrochemical biosensor |
US6134461A (en) | 1998-03-04 | 2000-10-17 | E. Heller & Company | Electrochemical analyte |
US6175752B1 (en) | 1998-04-30 | 2001-01-16 | Therasense, Inc. | Analyte monitoring device and methods of use |
EP1086506A1 (en) | 1998-05-12 | 2001-03-28 | Ecole Polytechnique Federale De Lausanne (Epfl) | Primary or secondary electrochemical generator |
US6294062B1 (en) | 1998-06-01 | 2001-09-25 | Roche Diagnostics Corporation | Method and device for electrochemical immunoassay of multiple analytes |
WO1999067628A1 (en) | 1998-06-24 | 1999-12-29 | Therasense, Inc. | Multi-sensor array for electrochemical recognition of nucleotide sequences and methods |
JP2997773B1 (ja) * | 1998-07-15 | 2000-01-11 | 工業技術院長 | 増感剤として有用な金属錯体、酸化物半導体電極及び太陽電池 |
US6338790B1 (en) * | 1998-10-08 | 2002-01-15 | Therasense, Inc. | Small volume in vitro analyte sensor with diffusible or non-leachable redox mediator |
US6616819B1 (en) * | 1999-11-04 | 2003-09-09 | Therasense, Inc. | Small volume in vitro analyte sensor and methods |
EP1230248B1 (en) | 1999-11-15 | 2007-06-06 | Therasense, Inc. | Transition metal complexes attached to a polymer via a flexible chain |
AU2001263022A1 (en) | 2000-05-12 | 2001-11-26 | Therasense, Inc. | Electrodes with multilayer membranes and methods of using and making the electrodes |
US6676816B2 (en) | 2001-05-11 | 2004-01-13 | Therasense, Inc. | Transition metal complexes with (pyridyl)imidazole ligands and sensors using said complexes |
ES2304508T3 (es) | 2002-05-20 | 2008-10-16 | Matsushita Electric Works, Ltd. | Dispositivo de conversion fotoelectrica. |
US7109271B2 (en) | 2004-07-28 | 2006-09-19 | Lifescan, Inc. | Redox polymers for use in electrochemical-based sensors |
JP4114012B2 (ja) | 2005-03-31 | 2008-07-09 | Dic株式会社 | 多分岐ポリエーテルポリオール |
-
2000
- 2000-11-14 EP EP00978573A patent/EP1230248B1/en not_active Expired - Lifetime
- 2000-11-14 ES ES00978635T patent/ES2222252T3/es not_active Expired - Lifetime
- 2000-11-14 AT AT00978635T patent/ATE268336T1/de not_active IP Right Cessation
- 2000-11-14 DE DE60011286T patent/DE60011286T2/de not_active Expired - Lifetime
- 2000-11-14 EP EP00978635A patent/EP1230249B1/en not_active Expired - Lifetime
- 2000-11-14 AU AU16078/01A patent/AU1607801A/en not_active Abandoned
- 2000-11-14 CA CA002391423A patent/CA2391423A1/en not_active Abandoned
- 2000-11-14 AU AU16026/01A patent/AU1602601A/en not_active Abandoned
- 2000-11-14 US US09/712,452 patent/US6605201B1/en not_active Expired - Lifetime
- 2000-11-14 DK DK00978635T patent/DK1230249T3/da active
- 2000-11-14 WO PCT/US2000/031268 patent/WO2001036430A1/en active IP Right Grant
- 2000-11-14 JP JP2001538538A patent/JP5308609B2/ja not_active Expired - Fee Related
- 2000-11-14 TR TR2004/01326T patent/TR200401326T4/xx unknown
- 2000-11-14 WO PCT/US2000/031126 patent/WO2001036660A2/en active IP Right Grant
- 2000-11-14 JP JP2001538919A patent/JP4932113B2/ja not_active Expired - Fee Related
- 2000-11-14 US US09/712,065 patent/US6605200B1/en not_active Expired - Lifetime
- 2000-11-14 AT AT00978573T patent/ATE364046T1/de not_active IP Right Cessation
- 2000-11-14 DE DE60035123T patent/DE60035123T2/de not_active Expired - Fee Related
- 2000-11-14 CA CA2391425A patent/CA2391425C/en not_active Expired - Lifetime
-
2003
- 2003-08-11 US US10/639,181 patent/US7090756B2/en not_active Expired - Lifetime
-
2006
- 2006-08-10 US US11/503,519 patent/US7918976B2/en not_active Expired - Fee Related
-
2009
- 2009-02-13 US US12/371,504 patent/US8092662B2/en not_active Expired - Fee Related
-
2010
- 2010-07-26 US US12/843,607 patent/US8168052B2/en not_active Expired - Fee Related
-
2011
- 2011-08-22 US US13/215,009 patent/US8512534B2/en not_active Expired - Fee Related
- 2011-08-22 US US13/214,999 patent/US8795490B2/en not_active Expired - Fee Related
- 2011-08-22 US US13/215,007 patent/US8828204B2/en not_active Expired - Fee Related
-
2014
- 2014-08-27 US US14/470,660 patent/US9320467B2/en not_active Expired - Fee Related
-
2016
- 2016-04-20 US US15/134,116 patent/US10219730B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5308609B2 (ja) | ポリマー遷移金属錯体及びその用途 | |
JP4420899B2 (ja) | (ピリジル)イミダゾール配位子を有する遷移金属錯体 | |
AU2019341169B2 (en) | Oxidation-reduction polymer including transition metal complex, and electrochemical biosensor using same | |
AU2007231899B2 (en) | Transition metal complexes with (pyridyl)imidazole ligands | |
AU2011239358A1 (en) | Transition metal complexes with (pyridyl)imidazole ligands |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20071112 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20071112 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20100802 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100824 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20101124 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20101201 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110223 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20111108 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120208 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120522 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120820 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130604 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130701 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 5308609 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |