CN1174079C - Fluorescent compound with piperazine radial and its application in positive ion supersensitive light signal identification - Google Patents
Fluorescent compound with piperazine radial and its application in positive ion supersensitive light signal identification Download PDFInfo
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- CN1174079C CN1174079C CNB011423102A CN01142310A CN1174079C CN 1174079 C CN1174079 C CN 1174079C CN B011423102 A CNB011423102 A CN B011423102A CN 01142310 A CN01142310 A CN 01142310A CN 1174079 C CN1174079 C CN 1174079C
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- fluorescent
- transition metal
- straight
- metal ion
- fluorescence
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title abstract description 15
- 239000007850 fluorescent dye Substances 0.000 title description 2
- 229910001428 transition metal ion Inorganic materials 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 4
- 238000012443 analytical study Methods 0.000 claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 125000001302 tertiary amino group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 28
- 150000002500 ions Chemical class 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000012530 fluid Substances 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 239000012528 membrane Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical class CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000000536 complexating effect Effects 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- -1 iron ion Chemical class 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 150000008431 aliphatic amides Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The present invention provides fluorescent switching compounds with four piperazine radicals, which can be used for supersensitive light signal identification of positive ions. After being combined with transition metal ions and hydrogen protons, the fluorescent compounds have obviously strengthened fluorescence and excellent switching performance. The fluorescent switching compounds can be used as molecular fluorescent switches to detect transition metal ions, pH value, acid organic mediums, etc. in macro and microenvironments. The fluorescent switching compounds have an important value in the analysis and the inspection of biological tissues, cells, membranes and other microenvironments as well as reagents, medicines and fluids.
Description
Technical field the present invention relates to four kinds of novel piperazinyl fluorescent chemicalses of a class and the application in transition metal ion and the super quick optical signal identification of hydrogen proton thereof.
Background technology is utilized the photoinduction transfer transport, and (Photoinduced Electron Transfer, it is comparatively common and realized commercialization that PET) organic fluorescent compounds developed of principle design is used for the mark of the detection of biological microenvironment hydrogen proton or acidic component.But but comparatively rare at the fluorescent probe that the transition metal ion that plays an important role in biology and environmental system is developed, this may be because generally transition metal ion has intensive cancellation effect to fluorescence.Several transition metal ion fluorescent switch (or probe) of having reported, perhaps complex structure, manufacturing cost is very high, perhaps to ionic susceptibility not high (the fluorescence intensification factor that the transition metal ion complexing causes has only several times to tens times).PET fluorescent switch molecular system connects base generally by fluorescent chromophore, and acceptor three parts are formed.Existing various PET fluorescent switch molecule (comprises and is used for H
+With metal ion detection) in be connected that base is most to adopt flexible monoalkyl chains (containing 1-3 carbon), indivedual use inflexible that have only of having reported connect the fluorescent switch of basic (as phenyl ring).
Summary of the invention the objective of the invention is to develop simple in structure, and to transition metal ion, the hydrogen proton all has the fluorescent switch compound of hypersensitivity.It will play a role in microenvironments such as biological tissue, cell, film and reagent, medicine, fluidic analytical study.
Relate to four kinds of compounds of a class among the present invention and have following general structure respectively:
R wherein
1=H ,-CN; R
2=-CN; R
3=-H, C
1～C
12Straight or branched alkane ,-C
2H
4OH;
R
4=C
2～C
12The straight or branched alkyl ,-CH
2CH
2OH; R
5=-H, C
1～C
12Straight or branched alkane ,-C
2H
4OH;
R
6=-H, C
1～C
12Straight or branched alkane ,-C
2H
4OH; R
7=-H, C
1～C
12Straight or branched alkane ,-C
2H
4OH
The fluorescent chromophore that design of the present invention is adopted in structure design has very high quantum yield, pushes away strongly-the La electron system.Fluorescent chromophore push away electronics position one side, link to each other with acceptor by connecting base, such layout help electronics from acceptor to chromophoric transfer.Acceptor portion is the simplest tertiary amine or secondary amine, rather than the complicated acceptor such as crown ether, reduces manufacturing cost.Connect base and then adopt half firm semiflexible piperazine ring, this is to be beneficial to the transfer transport of system owing to consider the rigidity that fluorescent chemicals should have an appropriateness, and avoid since transition metal ion near the fluorophore in the compound and contingent cancellation effect; Have certain flexibility simultaneously so that when complexing ion, can make suitable configuration adjustment, increase the ability of complexing, detect lower limit thereby reduce.The amino that links to each other with aromatic ring on (4-alkyl) piperazine ring becomes the electron-donating group of fluorescent chromophore, the aliphatic amide part is then as electron donor(ED) and the metal ion and the hydrogen proton combined function group of photoinduction transfer transport, and the six-ring skeleton is as the path of photoinduction transfer transport.
All can adopt following universal method synthetic to above four kinds of compounds: 1) piperazine or 4-alkylpiperazine carry out nucleophilic substitution reaction with corresponding halo chromophoric group precursor.Wherein II, III kind compound also can be synthesized with piperazine or 4-alkylpiperazine nucleophilic substitution reaction by its nitro replacement chromophoric group precursor.2) 4-alkylpiperazine substitution compound is synthetic, also can adopt the product of piperazine and halo or nitro replacement chromophoric group precursor nucleophilic reaction and haloalkane or other alkylating reagents to carry out the tertiary amine reaction and prepare.
For example: synthetic formula (I), available chromophoric group halogenated compound and piperazine and derivative thereof, the certain hour that in solvent, refluxes, decompression steams partial solvent then, separates out product, filters, and can make product (I):
R wherein
1, R
2, R
3Represent foregoing substituted radical.
Synthetic general formula (II) or (III) compound, chromophore compound and piperazine and derivative thereof that available nitro replaces, in solvent, in 20-100 ℃ of reaction down, decompression steams partial solvent, separates out solid, and filtration makes product (II):
R wherein
4, R
5Represent foregoing substituted radical.
Synthetic general formula (IV) compound, available nitro halogenated compound and piperazine and derivative thereof react certain hour under the low temperature in solvent, and decompression steams partial solvent, separates out product, filters, and obtains product (IV):
R wherein
7Represent foregoing substituted radical.
Fluorescent switch compound of the present invention can be used as the super quick optical signal identification of positive ion, can be at multiple common solvent such as methyl alcohol, ethanol, Virahol, in the acetonitrile etc. with multiple transition metal ion such as Cr
3+, Fe
3+, Cu
2+, CO
2+, Ni
2+And Mn
2+, Hg
2+, Zn
2+, Ag
-Strengthen (fluorescence quantum efficiency for the 100-200 before the coupled ion not doubly) Deng combining and show very big fluorescence, the fluorescence maximum emission wavelength also can move 15-30nrn to the shortwave direction simultaneously.
The characteristics of fluorescent switch compound of the present invention are for adopting piperazine ring as connecting base, and are simple in structure, and transition metal ion and hydrogen proton are all had good switch.
Fluorescent switch compound (I), (II), (III), (IV) have important value in biological tissue, cell, film microenvironment and reagent, medicine, fluidic analytical study.
Figure of description 1 be iron ion to compound 1-1 fluorescence influence, ordinate is a fluorescence quantum efficiency, abscissa is an iron concentration (10
-6Mol/L);
Figure of description 2 for the pH value to compound 1-1 fluorescence influence, ordinate is a fluorescence quantum efficiency, abscissa is the pH value.
Fluorescent switch compound of the present invention fluorescence intensity in different pH value media has considerable change: very weak at alkaline medium fluorescence, strengthen very big (fluorescence quantum efficiency is 200-400 times under the alkaline condition) at neutral and acidic medium fluorescence.
Embodiment
Embodiment 1
1 restrains 4-bromonaphthalene dintrile, is dissolved in the 10 gram pyridines, adds 1.6 gram N methyl piperazines, refluxes 3 hours, behind the concentrating under reduced pressure solvent, filters, and gets product, and product I-1 is a yellow solid, yield 80%, fusing point: 214-215 ℃
1H?NMR(CDCI
3，400M)δ2.55(s，3H，-CH
3)，2.90(s，4H，-NCH
2CH
2NCH
3)，3.30(s，4H，-NCH
2CH
2NCH
3)，7.21(d，J＝8Hz，1H)，7.62(t，J＝8Hz，1H)，8.02(d，J＝7.6Hz，1H)，8.08(d，J＝7.2Hz，1H)，8.46(d，J＝8.4Hz，1H)。
Embodiment 2
1 gram 4-nitro-1,8-naphthoyl fourth imines is dissolved in 10 and restrains dimethyl formamides (being DMF), adds 1.4 gram N methyl piperazines, and room temperature is placed diel, behind the concentrated solvent, filters, and gets product, and product II is a yellow solid, yield 90%, fusing point: 120-121 ℃;
1H?NMR(CDCL
3，400M)δ2.52(s，3H，-CH
3)，2.92(s，4H，-NCH
2CH
2NCH
3)，3.37(s，4H，-NCH
2CH
2NCH
3)，3.82(t，J＝6.8Hz，-CH
2CH
2OH)，4.35(t，J＝6.4Hz，-CH
2CH
2OH)，7.25(d，J＝8Hz，1H)，7.72(t，J＝8Hz，1H)，8.42(d，J＝8.4Hz，1H)，8.48(d，J＝8Hz，1H)，8.55(d，J＝7.2Hz，1H)。
Embodiment 3
1 gram Cl-NBD is dissolved in 5 gram methylene dichloride, and 2 parts of N methyl piperazines are dissolved in 5 gram methylene dichloride, and ice bath stirs down, and the latter is slowly splashed among the former, drips off the back and keeps 2 hours, concentrates, and separates out solid, filters and obtains product, and product IV-1 is a red solid, yield 85%.Fusing point: 184-185 ℃;
1H?NMR(CDCI
3，400M)δ2.39(s，3H，-CH
3)，2.67(t，4.8Hz，4H-CH
2NCH
3)，4.12(t，4.8Hz，4H，CH
2CH
2NCH
3)，6.30(d，9.2Hz，1H)，8.40(d，8.8Hz，1H)。
Embodiment 4
Compound I among the embodiment 1-1 is dissolved in that compound concentration is 1 * 10 in the ethanol
-6The solution of mol/L, measure its fluorescence spectrum: maximum emission wavelength is 482nm, and fluorescence quantum efficiency is 0.0034, and fluorescence intensity has increase in various degree when adding the iron trichloride of different amounts, and wavelength obviously moves to shortwave.As the Fe that adds
3+Concentration is 10 * 10
-6Fluorescence intensity reaches maximum value (continuation adding Fe during mol/L
3+Then fluorescence weakens on the contrary), this moment, maximum emission wavelength was 467nm, fluorescence quantum efficiency is 0.552, has increased 160 times when not adding iron trichloride.
Iron ion is to Compound I-1 fluorescence influence
Compound I-1 is not only to Fe
3+Show good fluorescent switch, simultaneously to other multiple transition metal ions as Cr
3+, Cu
2+, Co
2+, Ni
2+And Mn
2+, Hg
2+, Zn
2+, Ag
+Deng good susceptibility is also arranged.
Other compound among the present invention all shows highly sensitive fluorescent switch performance (after different transition metal ions combinations, fluorescence strengthens 100-200 doubly) to multiple transition metal ion.
Embodiment 5
Fluorescent switch Compound I-1 among the embodiment 1 is dissolved in methyl alcohol-0.05mol/L K
3PO
4The aqueous solution (V: V=1: 4) in the buffer system, regulate the pH value with dilute hydrochloric acid.Along with reducing of pH value, fluorescence intensity increases.Under alkaline condition (pH=11), fluorescence quantum efficiency is 0.0022, and under the acidic conditions (pH=3.2), fluorescence quantum efficiency is 0.601, is 273 times under the alkaline condition.
The pH value is to Compound I-1 fluorescence influence
Other compound among the present invention is all very responsive to the pH value, and the fluorescence quantum efficiency in the acidic medium is 200-400 times in the alkaline medium.
Claims (4)
1, a class by chromophoric group, connect the fluorescent chemicals that base and acceptor three parts are formed, the fluorescent chromophore that it is characterized in that this fluorescent chemicals is benzene series or naphthalene derivative, connecting base is piperazine ring, and acceptor is tertiary amine or secondary amine, and they have following general structure:
R wherein
1=H ,-CN; R
2=-CN; R
3=-H, C
1～C
12Straight or branched alkane ,-C
2H
4OH;
R
4=C
2～C
12The straight or branched alkyl ,-CH
2CH
2OH; R
5=-H, C
1～C
12Straight or branched alkane ,-C
2H
4OH;
R
6=-H, C
1～C
12Straight or branched alkane ,-C
2H
4OH; R
7=-H, C
1～C
12Straight or branched alkane ,-C
2H
4OH
2, a class is with the purposes of the described fluorescent chemicals of claim 1, it is characterized in that these four kinds of piperazinyl fluorescent chemicalses (I), (II), (III), (IV) can be used as the super quick optical signal identification of positive ion, strengthen fluorescence and good switch with transition metal ion and hydrogen proton-binding energy in methyl alcohol, ethanol, Virahol, acetonitrile.
3,, it is characterized in that transition metal ion has Cr according to the purposes of the described fluorescent chemicals of claim 2
3+, Fe
3+, Cu
2+, Co
2+, Ni
2+And Mn
2+, Hg
2+, Zn
2+, Ag
+
4, a class is with the purposes of the described fluorescent chemicals of claim 1, it is characterized in that four kinds of piperazinyl fluorescent chemicalses (I), (II), (III), (IV) as the molecular fluorescence switch, can detect transition metal ion, pH value, mor in macroscopic view and the microenvironment; In biological tissue, cell, film microenvironment and reagent, medicine, fluidic analytical study, important value is arranged.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB011423102A CN1174079C (en) | 2001-11-22 | 2001-11-22 | Fluorescent compound with piperazine radial and its application in positive ion supersensitive light signal identification |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB011423102A CN1174079C (en) | 2001-11-22 | 2001-11-22 | Fluorescent compound with piperazine radial and its application in positive ion supersensitive light signal identification |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1374366A CN1374366A (en) | 2002-10-16 |
| CN1174079C true CN1174079C (en) | 2004-11-03 |
Family
ID=4676753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB011423102A Expired - Fee Related CN1174079C (en) | 2001-11-22 | 2001-11-22 | Fluorescent compound with piperazine radial and its application in positive ion supersensitive light signal identification |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1174079C (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103342698B (en) * | 2013-07-31 | 2015-06-17 | 齐齐哈尔大学 | Application of dual-fluorophore ratio fluorescence molecular probe for non-fluorescence resonance energy transfer |
| CN104357063B (en) * | 2014-07-28 | 2016-04-13 | 大连理工大学 | Liquid crystalline cpd, its preparation method and application containing 4-(biphenyl ethynyl)-1,8-naphthalene dintrile |
| CN104293356B (en) * | 2014-07-28 | 2016-03-09 | 大连理工大学 | A kind of liquid crystalline cpd is as high birefringence rate liquid crystal material or improving the application in liquid crystal host degree of birefringence |
| CN104357045B (en) * | 2014-11-05 | 2016-06-01 | 北京化工大学 | There is synthetic method and the application thereof of the spiro-pyrans small-molecule fluorescent probe of extremely acid/pole alkali switching response |
| CN107652234A (en) * | 2017-09-13 | 2018-02-02 | 陕西科技大学 | Detect Cu (II) two-photon fluorescence probe and preparation method and application |
| CN108191760B (en) * | 2018-02-05 | 2020-11-27 | 陕西科技大学 | Fluorescent probe for detecting Cu (II) and preparation method and application thereof |
-
2001
- 2001-11-22 CN CNB011423102A patent/CN1174079C/en not_active Expired - Fee Related
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| Publication number | Publication date |
|---|---|
| CN1374366A (en) | 2002-10-16 |
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