JP7432529B2 - 広域スペクトルキナーゼ結合剤 - Google Patents
広域スペクトルキナーゼ結合剤 Download PDFInfo
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- JP7432529B2 JP7432529B2 JP2020566944A JP2020566944A JP7432529B2 JP 7432529 B2 JP7432529 B2 JP 7432529B2 JP 2020566944 A JP2020566944 A JP 2020566944A JP 2020566944 A JP2020566944 A JP 2020566944A JP 7432529 B2 JP7432529 B2 JP 7432529B2
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- QSHGUCSTWRSQAF-FJSLEGQWSA-N s-peptide Chemical compound C([C@@H](C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC(OS(O)(=O)=O)=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C1=CC=C(OS(O)(=O)=O)C=C1 QSHGUCSTWRSQAF-FJSLEGQWSA-N 0.000 description 1
- 239000002094 self assembled monolayer Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- RXFHRKPNLPBDGE-UHFFFAOYSA-N tert-butyl 4-(4-aminophenyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(N)C=C1 RXFHRKPNLPBDGE-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ABZLKHKQJHEPAX-UHFFFAOYSA-N tetramethylrhodamine Chemical compound C=12C=CC(N(C)C)=CC2=[O+]C2=CC(N(C)C)=CC=C2C=1C1=CC=CC=C1C([O-])=O ABZLKHKQJHEPAX-UHFFFAOYSA-N 0.000 description 1
- MPLHNVLQVRSVEE-UHFFFAOYSA-N texas red Chemical compound [O-]S(=O)(=O)C1=CC(S(Cl)(=O)=O)=CC=C1C(C1=CC=2CCCN3CCCC(C=23)=C1O1)=C2C1=C(CCC1)C3=[N+]1CCCC3=C2 MPLHNVLQVRSVEE-UHFFFAOYSA-N 0.000 description 1
- 108060008226 thioredoxin Proteins 0.000 description 1
- 229940094937 thioredoxin Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- 108010064892 trkC Receptor Proteins 0.000 description 1
- 108010072106 tumstatin (74-98) Proteins 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
- G01N33/54353—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals with ligand attached to the carrier via a chemical coupling agent
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N1/00—Sampling; Preparing specimens for investigation
- G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
- G01N1/34—Purifying; Cleaning
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/573—Immunoassay; Biospecific binding assay; Materials therefor for enzymes or isoenzymes
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6439—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" with indicators, stains, dyes, tags, labels, marks
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
- G01N2333/90—Enzymes; Proenzymes
- G01N2333/91—Transferases (2.)
- G01N2333/912—Transferases (2.) transferring phosphorus containing groups, e.g. kinases (2.7)
- G01N2333/91205—Phosphotransferases in general
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01R—MEASURING ELECTRIC VARIABLES; MEASURING MAGNETIC VARIABLES
- G01R33/00—Arrangements or instruments for measuring magnetic variables
- G01R33/20—Arrangements or instruments for measuring magnetic variables involving magnetic resonance
- G01R33/44—Arrangements or instruments for measuring magnetic variables involving magnetic resonance using nuclear magnetic resonance [NMR]
- G01R33/48—NMR imaging systems
- G01R33/54—Signal processing systems, e.g. using pulse sequences ; Generation or control of pulse sequences; Operator console
- G01R33/56—Image enhancement or correction, e.g. subtraction or averaging techniques, e.g. improvement of signal-to-noise ratio and resolution
- G01R33/5601—Image enhancement or correction, e.g. subtraction or averaging techniques, e.g. improvement of signal-to-noise ratio and resolution involving use of a contrast agent for contrast manipulation, e.g. a paramagnetic, super-paramagnetic, ferromagnetic or hyperpolarised contrast agent
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01T—MEASUREMENT OF NUCLEAR OR X-RADIATION
- G01T1/00—Measuring X-radiation, gamma radiation, corpuscular radiation, or cosmic radiation
- G01T1/16—Measuring radiation intensity
- G01T1/161—Applications in the field of nuclear medicine, e.g. in vivo counting
- G01T1/164—Scintigraphy
- G01T1/1641—Static instruments for imaging the distribution of radioactivity in one or two dimensions using one or several scintillating elements; Radio-isotope cameras
- G01T1/1642—Static instruments for imaging the distribution of radioactivity in one or two dimensions using one or several scintillating elements; Radio-isotope cameras using a scintillation crystal and position sensing photodetector arrays, e.g. ANGER cameras
Description
(CC-1852)。
(CC-1861)。
(CTx-0294885)。
が機能的要素または固体表面に結合されたもの(CC-1816、CC-1817など)。
が機能的要素または固体表面に結合されたもの(CC-1803、CC-1804など)。
が機能的要素または固体表面に結合されたもの(CC-1290、CC-1294など)。
(式中、Xは機能的要素または固体表面である)。いくつかの実施形態では、Xはフルオロフォアである。いくつかの実施形態では、本明細書において下記構造を有する広域スペクトルキナーゼ結合剤が提供される。
(式中、Xは機能的要素または固体表面である)。いくつかの実施形態では、Xはフルオロフォアである。いくつかの実施形態では、本明細書において下記構造を有する広域スペクトルキナーゼ結合剤が提供される。
(式中、Xは機能的要素または固体表面である)。いくつかの実施形態では、Xはフルオロフォアである。いくつかの実施形態では、本明細書において下記構造を有する広域スペクトルキナーゼ結合剤が提供される。
本明細書に記載される方法及び材料と同様、または同等のいずれの方法及び材料も本発明の実施または試験にあたって使用することが可能であるが、いくつかの好ましい実施形態の組成物、方法、及び材料を本明細書で説明する。しかしながら、本明細書に記載される特定の分子、組成物、方法論またはプロトコールは、通常の実験手法及び最適化に従って異なり得るため、本発明はこれらに限定されない点を、本材料及び方法を説明するのに先立って理解されたい。また、本明細書において使用される用語は、あくまで本発明の特定の型または実施形態を説明するためのものであって、本明細書に記載される実施形態の範囲を限定することを目的としたものではない点を理解されたい。
(CC-1852)
または、下記構造を有する分子実体の部分/置換基:
(例、CC-1816、CC-1817)を指す。
(CC-1861)、または
下記構造を有する分子実体の部分/置換基:
(例、CC-1803、CC-1804など)を指す。
(CTx-0294885)、または
下記構造を有する分子実体の部分/置換基:
(例、CC-1294、CC-1290など)を指す。
本明細書では、広域スペクトルプロテインキナーゼ結合剤である化合物、かかる化合物を含む検出可能なトレーサー、及びプロテインキナーゼの検出のためのその使用方法を提供する。
(CC-1861)、
(CC-1852)、
(CTx-0294885)、
が提供される。いくつかの実施形態では、本明細書において、CC-1861、CC-1852、及び/またはCTx-0294885部分を含む化合物または分子実体:
(例、CC-1803、CC-1804)、
(例、CC-1816、CC-1817)、
(例、CC-1290、CC-1294)、
機能的要素(例えば、CC-1861、CC-1852、CTx-0294885のピペラジンの4位の窒素に結合したもの)が提供される。いくつかの実施形態では、本明細書において、CC-1852、CC-1861、CTx-0294885の類似体または誘導体、及び/またはCC-1852、CC-1861、CTx-0294885の類似体または誘導体を含む化合物または分子実体、ならびに機能的要素(例えば、CC-1816、CC-1817、CC-1803、CC-1804、CC-1290、CC-1294などの類似体または誘導体)が提供される。いくつかの実施形態では、CC-1852、CC-1861、CTx-0294885、またはそれらの類似体または誘導体は、機能的要素に直接(単一の共有結合を介して)結合される。いくつかの実施形態では、CC-1852、CC-1861、CTx-0294885、またはそれらの類似体または誘導体(例えば、CC-1816、CC-1817、CC-1803、CC-1804、CC-1290、CC1294など)は、機能的要素に間接的に(リンカーを介して)結合される。
表1A AGC Ser / Thrプロテインキナーゼファミリー
=================================
AKT1 AKT1_HUMAN (P31749 ) AKT1_MOUSE (P31750)
AKT2 AKT2_HUMAN (P31751 ) AKT2_MOUSE (Q60823)
AKT3 AKT3_HUMAN (Q9Y243 ) AKT3_MOUSE (Q9WUA6)
CDC42BPA MRCKA_HUMAN(Q5VT25)MRCKA_MOUSE(Q3UU96)
CDC42BPB MRCKB_HUMAN(Q9Y5S2)MRCKB_MOUSE(Q7TT50)
CDC42BPG MRCKG_HUMAN(Q6DT37)MRCKG_MOUSE(Q80UW5)
CIT CTRO_HUMAN(O14578)CTRO_MOUSE(P49025)
DMPK DMPK_HUMAN(Q09013)DMPK_MOUSE(P54265)
GRK1 RK_HUMAN(Q15835)RK_MOUSE(Q9WVL4)
GRK2 ARBK1_HUMAN (P25098 ) ARBK1_MOUSE (Q99MK8)
GRK3 ARBK2_HUMAN (P35626 ) ARBK2_MOUSE (Q3UYH7)
GRK4 GRK4_HUMAN (P32298 ) GRK4_MOUSE (O70291)
GRK5 GRK5_HUMAN (P34947 ) GRK5_MOUSE (Q8VEB1)
GRK6 GRK6_HUMAN (P43250 ) GRK6_MOUSE (O70293)
GRK7 GRK7_HUMAN (Q8WTQ7 )
LATS1 LATS1_HUMAN (O95835 ) LATS1_MOUSE (Q8BYR2)
LATS2 LATS2_HUMAN (Q9NRM7 ) LATS2_MOUSE (Q7TSJ6)
MAST1 MAST1_HUMAN (Q9Y2H9 ) MAST1_MOUSE (Q9R1L5)
MAST2 MAST2_HUMAN (Q6P0Q8 ) MAST2_MOUSE (Q60592)
MAST3 MAST3_HUMAN (O60307 ) MAST3_MOUSE (Q3U214)
MAST4 MAST4_HUMAN (O15021 ) MAST4_MOUSE (Q811L6)
MASTL GWL_HUMAN(Q96GX5)GWL_MOUSE(Q8C0P0)
PDPK1 PDPK1_HUMAN (O15530 ) PDPK1_MOUSE (Q9Z2A0)
PDPK2P PDPK2_HUMAN (Q6A1A2 )
PKN1 PKN1_HUMAN (Q16512 ) PKN1_MOUSE (P70268)
PKN2 PKN2_HUMAN (Q16513 ) PKN2_MOUSE (Q8BWW9)
PKN3 PKN3_HUMAN (Q6P5Z2 ) PKN3_MOUSE (Q8K045)
PRKACA KAPCA_HUMAN(P17612)KAPCA_MOUSE(P05132)
PRKACB KAPCB_HUMAN(P22694)KAPCB_MOUSE(P68181)
PRKACG KAPCG_HUMAN(P22612)
PRKCA KPCA_HUMAN(P17252)KPCA_MOUSE(P20444)
PRKCB KPCB_HUMAN(P05771)KPCB_MOUSE(P68404)
PRKCD KPCD_HUMAN(Q05655)KPCD_MOUSE(P28867)
PRKCE KPCE_HUMAN(Q02156)KPCE_MOUSE(P16054)
PRKCG KPCG_HUMAN(P05129)KPCG_MOUSE(P63318)
PRKCH KPCL_HUMAN(P24723)KPCL_MOUSE(P23298)
PRKCI KPCI_HUMAN(P41743)KPCI_MOUSE(Q62074)
PRKCQ KPCT_HUMAN(Q04759)KPCT_MOUSE(Q02111)
PRKCZ KPCZ_HUMAN(Q05513)KPCZ_MOUSE(Q02956)
PRKG1 KGP1_HUMAN (Q13976 ) KGP1_MOUSE (P0C605)
PRKG2 KGP2_HUMAN (Q13237 ) KGP2_MOUSE (Q61410)
PRKX PRKX_HUMAN(P51817)PRKX_MOUSE(Q922R0)
PRKY PRKY_HUMAN(O43930)
ROCK1 ROCK1_HUMAN (Q13464 ) ROCK1_MOUSE (P70335)
ROCK2 ROCK2_HUMAN (O75116 ) ROCK2_MOUSE (P70336)
RPS6KA1 KS6A1_HUMAN (Q15418 ) KS6A1_MOUSE (P18653)
RPS6KA2 KS6A2_HUMAN (Q15349 ) KS6A2_MOUSE (Q9WUT3)
RPS6KA3 KS6A3_HUMAN (P51812 ) KS6A3_MOUSE (P18654)
RPS6KA4 KS6A4_HUMAN (O75676 ) KS6A4_MOUSE (Q9Z2B9)
RPS6KA5 KS6A5_HUMAN (O75582 ) KS6A5_MOUSE (Q8C050)
RPS6KA6 KS6A6_HUMAN (Q9UK32 ) KS6A6_MOUSE (Q7TPS0)
RPS6KB1 KS6B1_HUMAN (P23443 ) KS6B1_MOUSE (Q8BSK8)
RPS6KB2 KS6B2_HUMAN (Q9UBS0 ) KS6B2_MOUSE (Q9Z1M4)
SGK1 SGK1_HUMAN (O00141 ) SGK1_MOUSE (Q9WVC6)
SGK2 SGK2_HUMAN (Q9HBY8 ) SGK2_MOUSE (Q9QZS5)
SGK3 SGK3_HUMAN (Q96BR1 ) SGK3_MOUSE (Q9ERE3)
STK38 STK38_HUMAN (Q15208 ) STK38_MOUSE (Q91VJ4)
STK38L ST38L_HUMAN (Q9Y2H1 ) ST38L_MOUSE (Q7TSE6)
==================================
表1B CAMK Ser / Thrプロテインキナーゼファミリー
==================================
SMKX_MOUSE(Q8C0X8)
BRSK1 BRSK1_HUMAN (Q8TDC3 ) BRSK1_MOUSE (Q5RJI5)
BRSK2 BRSK2_HUMAN (Q8IWQ3 ) BRSK2_MOUSE (Q69Z98)
CAMK1 KCC1A_HUMAN (Q14012 ) KCC1A_MOUSE (Q91YS8)
CAMK1D KCC1D_HUMAN (Q8IU85 ) KCC1D_MOUSE (Q8BW96)
CAMK1G KCC1G_HUMAN (Q96NX5 ) KCC1G_MOUSE (Q91VB2)
CAMK2A KCC2A_HUMAN (Q9UQM7 ) KCC2A_MOUSE (P11798)
CAMK2B KCC2B_HUMAN (Q13554 ) KCC2B_MOUSE (P28652)
CAMK2D KCC2D_HUMAN (Q13557 ) KCC2D_MOUSE (Q6PHZ2)
CAMK2G KCC2G_HUMAN (Q13555 ) KCC2G_MOUSE (Q923T9)
CAMK4 KCC4_HUMAN (Q16566 ) KCC4_MOUSE (P08414)
CAMKV CAMKV_HUMAN(Q8NCB2)CAMKV_MOUSE(Q3UHL1)
CASK CSKP_HUMAN(O14936)CSKP_MOUSE(O70589)
CHEK1 CHK1_HUMAN (O14757 ) CHK1_MOUSE (O35280)
CHEK2 CHK2_HUMAN (O96017 ) CHK2_MOUSE (Q9Z265)
DAPK1 DAPK1_HUMAN (P53355 ) DAPK1_MOUSE (Q80YE7)
DAPK2 DAPK2_HUMAN (Q9UIK4 ) DAPK2_MOUSE (Q8VDF3)
DAPK3 DAPK3_HUMAN (O43293 ) DAPK3_MOUSE (O54784)
DCLK1 DCLK1_HUMAN (O15075 ) DCLK1_MOUSE (Q9JLM8)
DCLK2 DCLK2_HUMAN (Q8N568 ) DCLK2_MOUSE (Q6PGN3)
DCLK3 DCLK3_HUMAN (Q9C098 ) DCLK3_MOUSE (Q8BWQ5)
Gm4922 SMKZ_MOUSE(Q8C0N0)
Gm7168 SMKY_MOUSE(A0AUV4)
HUNK HUNK_HUMAN(P57058)HUNK_MOUSE(O88866)
KALRN KALRN_HUMAN(O60229)KALRN_MOUSE(A2CG49)
MAPKAPK2 MAPK2_HUMAN (P49137 ) MAPK2_MOUSE (P49138)
MAPKAPK3 MAPK3_HUMAN (Q16644 ) MAPK3_MOUSE (Q3UMW7)
MAPKAPK5 MAPK5_HUMAN (Q8IW41 ) MAPK5_MOUSE (O54992)
MARK1 MARK1_HUMAN (Q9P0L2 ) MARK1_MOUSE (Q8VHJ5)
MARK2 MARK2_HUMAN (Q7KZI7 ) MARK2_MOUSE (Q05512)
MARK3 MARK3_HUMAN (P27448 ) MARK3_MOUSE (Q03141)
MARK4 MARK4_HUMAN (Q96L34 ) MARK4_MOUSE (Q8CIP4)
MELK MELK_HUMAN(Q14680)MELK_MOUSE(Q61846)
MKNK1 MKNK1_HUMAN (Q9BUB5 ) MKNK1_MOUSE (O08605)
MKNK2 MKNK2_HUMAN (Q9HBH9 ) MKNK2_MOUSE (Q8CDB0)
MYLK MYLK_HUMAN(Q15746)MYLK_MOUSE(Q6PDN3)
MYLK2 MYLK2_HUMAN (Q9H1R3 ) MYLK2_MOUSE (Q8VCR8)
MYLK3 MYLK3_HUMAN (Q32MK0 ) MYLK3_MOUSE (Q3UIZ8)
MYLK4 MYLK4_HUMAN (Q86YV6 ) MYLK4_MOUSE (Q5SUV5)
NIM1K NIM1_HUMAN (Q8IY84 ) NIM1_MOUSE (Q8BHI9)
NUAK1 NUAK1_HUMAN (O60285 ) NUAK1_MOUSE (Q641K5)
NUAK2 NUAK2_HUMAN (Q9H093 ) NUAK2_MOUSE (Q8BZN4)
OBSCN OBSCN_HUMAN(Q5VST9)OBSCN_MOUSE(A2AAJ9)
PASK PASK_HUMAN(Q96RG2)PASK_MOUSE(Q8CEE6)
PHKG1 PHKG1_HUMAN (Q16816 ) PHKG1_MOUSE (P07934)
PHKG2 PHKG2_HUMAN (P15735 ) PHKG2_MOUSE (Q9DB30)
PIM1 PIM1_HUMAN (P11309 ) PIM1_MOUSE (P06803)
PIM2 PIM2_HUMAN (Q9P1W9 ) PIM2_MOUSE (Q62070)
PIM3 PIM3_HUMAN (Q86V86 ) PIM3_MOUSE (P58750)
PNCK KCC1B_HUMAN(Q6P2M8)KCC1B_MOUSE(Q9QYK9)
PRKAA1 AAPK1_HUMAN (Q13131 ) AAPK1_MOUSE (Q5EG47)
PRKAA2 AAPK2_HUMAN (P54646 ) AAPK2_MOUSE (Q8BRK8)
PRKD1 KPCD1_HUMAN (Q15139 ) KPCD1_MOUSE (Q62101)
PRKD2 KPCD2_HUMAN (Q9BZL6 ) KPCD2_MOUSE (Q8BZ03)
PRKD3 KPCD3_HUMAN (O94806 ) KPCD3_MOUSE (Q8K1Y2)
PSKH1 KPSH1_HUMAN (P11801 ) KPSH1_MOUSE (Q91YA2)
PSKH2 KPSH2_HUMAN (Q96QS6 )
SIK1 SIK1_HUMAN (P57059 ) SIK1_MOUSE (Q60670)
SIK2 SIK2_HUMAN (Q9H0K1 ) SIK2_MOUSE (Q8CFH6)
SIK3 SIK3_HUMAN (Q9Y2K2 ) SIK3_MOUSE (Q6P4S6)
SNRK SNRK_HUMAN(Q9NRH2)SNRK_MOUSE(Q8VDU5)
SPEG SPEG_HUMAN(Q15772)SPEG_MOUSE(Q62407)
STK11 STK11_HUMAN (Q15831 ) STK11_MOUSE (Q9WTK7)
STK17A ST17A_HUMAN (Q9UEE5 )
STK17B ST17B_HUMAN (O94768 ) ST17B_MOUSE (Q8BG48)
STK33 STK33_HUMAN (Q9BYT3 ) STK33_MOUSE (Q924X7)
STK40 STK40_HUMAN (Q8N2I9 ) STK40_MOUSE (Q7TNL3)
Smok2a SMK2A_MOUSE (Q9QYZ6)
Smok2b SMK2B_MOUSE (Q9QYZ3)
Smok3a SMK3A_MOUSE (C0HKC8)
Smok3b SMK3B_MOUSE (C0HKC9)
Stk-ps2 SMKW_MOUSE(Q8C0V7)
TRIB1 TRIB1_HUMAN (Q96RU8 ) TRIB1_MOUSE (Q8K4K4)
TRIB2 TRIB2_HUMAN (Q92519 ) TRIB2_MOUSE (Q8K4K3)
TRIB3 TRIB3_HUMAN (Q96RU7 ) TRIB3_MOUSE (Q8K4K2)
TRIO TRIO_HUMAN(O75962)TRIO_MOUSE(Q0KL02)
TSSK1B TSSK1_HUMAN (Q9BXA7 ) TSSK1_MOUSE (Q61241)
TSSK2 TSSK2_HUMAN (Q96PF2 ) TSSK2_MOUSE (O54863)
TSSK3 TSSK3_HUMAN (Q96PN8 ) TSSK3_MOUSE (Q9D2E1)
TSSK4 TSSK4_HUMAN (Q6SA08 ) TSSK4_MOUSE (Q9D411)
TSSK6 TSSK6_HUMAN (Q9BXA6 ) TSSK6_MOUSE (Q925K9)
TTN TITIN_HUMAN(Q8WZ42)TITIN_MOUSE(A2ASS6)
Tssk5 TSSK5_MOUSE (Q8C1R0)
=================================
表1C CK1 Ser / Thrプロテインキナーゼファミリー
=================================
CSNK1A1 KC1A_HUMAN (P48729 ) KC1A_MOUSE (Q8BK63)
CSNK1A1L KC1AL_HUMAN (Q8N752 )
CSNK1D KC1D_HUMAN (P48730 ) KC1D_MOUSE (Q9DC28)
CSNK1E KC1E_HUMAN (P49674 ) KC1E_MOUSE (Q9JMK2)
CSNK1G1 KC1G1_HUMAN (Q9HCP0 ) KC1G1_MOUSE (Q8BTH8)
CSNK1G2 KC1G2_HUMAN (P78368 ) KC1G2_MOUSE (Q8BVP5)
CSNK1G3 KC1G3_HUMAN (Q9Y6M4 ) KC1G3_MOUSE (Q8C4X2)
TTBK1 TTBK1_HUMAN (Q5TCY1 ) TTBK1_MOUSE (Q6PCN3)
TTBK2 TTBK2_HUMAN (Q6IQ55 ) TTBK2_MOUSE (Q3UVR3)
VRK1 VRK1_HUMAN (Q99986 ) VRK1_MOUSE (Q80X41)
VRK2 VRK2_HUMAN (Q86Y07 ) VRK2_MOUSE (Q8BN21)
VRK3 VRK3_HUMAN (Q8IV63 ) VRK3_MOUSE (Q8K3G5)
==================================
表1D CMGC Ser / Thrプロテインキナーゼファミリー
==================================
CDK1 CDK1_HUMAN (P06493 ) CDK1_MOUSE (P11440)
CDK10 CDK10_HUMAN (Q15131 ) CDK10_MOUSE (Q3UMM4)
CDK11A CD11A_HUMAN (Q9UQ88 )
CDK11B CD11B_HUMAN (P21127 ) CD11B_MOUSE (P24788)
CDK12 CDK12_HUMAN (Q9NYV4 ) CDK12_MOUSE (Q14AX6)
CDK13 CDK13_HUMAN (Q14004 ) CDK13_MOUSE (Q69ZA1)
CDK14 CDK14_HUMAN (O94921 ) CDK14_MOUSE (O35495)
CDK15 CDK15_HUMAN (Q96Q40 ) CDK15_MOUSE (Q3V3A1)
CDK16 CDK16_HUMAN (Q00536 ) CDK16_MOUSE (Q04735)
CDK17 CDK17_HUMAN (Q00537 ) CDK17_MOUSE (Q8K0D0)
CDK18 CDK18_HUMAN (Q07002 ) CDK18_MOUSE (Q04899)
CDK19 CDK19_HUMAN (Q9BWU1 ) CDK19_MOUSE (Q8BWD8)
CDK2 CDK2_HUMAN (P24941 ) CDK2_MOUSE (P97377)
CDK20 CDK20_HUMAN (Q8IZL9 ) CDK20_MOUSE (Q9JHU3)
CDK3 CDK3_HUMAN (Q00526 ) CDK3_MOUSE (Q80YP0)
CDK4 CDK4_HUMAN (P11802 ) CDK4_MOUSE (P30285)
CDK5 CDK5_HUMAN (Q00535 ) CDK5_MOUSE (P49615)
CDK6 CDK6_HUMAN (Q00534 ) CDK6_MOUSE (Q64261)
CDK7 CDK7_HUMAN (P50613 ) CDK7_MOUSE (Q03147)
CDK8 CDK8_HUMAN (P49336 ) CDK8_MOUSE (Q8R3L8)
CDK9 CDK9_HUMAN (P50750 ) CDK9_MOUSE (Q99J95)
CDKL1 CDKL1_HUMAN (Q00532 ) CDKL1_MOUSE (Q8CEQ0)
CDKL2 CDKL2_HUMAN (Q92772 ) CDKL2_MOUSE (Q9QUK0)
CDKL3 CDKL3_HUMAN (Q8IVW4 ) CDKL3_MOUSE (Q8BLF2)
CDKL4 CDKL4_HUMAN (Q5MAI5 ) CDKL4_MOUSE (Q3TZA2)
CDKL5 CDKL5_HUMAN (O76039 ) CDKL5_MOUSE (Q3UTQ8)
CLK1 CLK1_HUMAN (P49759 ) CLK1_MOUSE (P22518)
CLK2 CLK2_HUMAN (P49760 ) CLK2_MOUSE (O35491)
CLK3 CLK3_HUMAN (P49761 ) CLK3_MOUSE (O35492)
CLK4 CLK4_HUMAN (Q9HAZ1 ) CLK4_MOUSE (O35493)
DYRK1A DYR1A_HUMAN (Q13627 ) DYR1A_MOUSE (Q61214)
DYRK1B DYR1B_HUMAN (Q9Y463 ) DYR1B_MOUSE (Q9Z188)
DYRK2 DYRK2_HUMAN (Q92630 ) DYRK2_MOUSE (Q5U4C9)
DYRK3 DYRK3_HUMAN (O43781 ) DYRK3_MOUSE (Q922Y0)
DYRK4 DYRK4_HUMAN (Q9NR20 ) DYRK4_MOUSE (Q8BI55)
GSK3A GSK3A_HUMAN (P49840 ) GSK3A_MOUSE (Q2NL51)
GSK3B GSK3B_HUMAN (P49841 ) GSK3B_MOUSE (Q9WV60)
HIPK1 HIPK1_HUMAN (Q86Z02 ) HIPK1_MOUSE (O88904)
HIPK2 HIPK2_HUMAN (Q9H2X6 ) HIPK2_MOUSE (Q9QZR5)
HIPK3 HIPK3_HUMAN (Q9H422 ) HIPK3_MOUSE (Q9ERH7)
HIPK4 HIPK4_HUMAN (Q8NE63 ) HIPK4_MOUSE (Q3V016)
ICK ICK_HUMAN(Q9UPZ9)ICK_MOUSE(Q9JKV2)
MAK MAK_HUMAN(P20794)MAK_MOUSE(Q04859)
MAPK1 MK01_HUMAN (P28482 ) MK01_MOUSE (P63085)
MAPK10 MK10_HUMAN (P53779 ) MK10_MOUSE (Q61831)
MAPK11 MK11_HUMAN (Q15759 ) MK11_MOUSE (Q9WUI1)
MAPK12 MK12_HUMAN (P53778 ) MK12_MOUSE (O08911)
MAPK13 MK13_HUMAN (O15264 ) MK13_MOUSE (Q9Z1B7)
MAPK14 MK14_HUMAN (Q16539 ) MK14_MOUSE (P47811)
MAPK15 MK15_HUMAN (Q8TD08 ) MK15_MOUSE (Q80Y86)
MAPK3 MK03_HUMAN (P27361 ) MK03_MOUSE (Q63844)
MAPK4 MK04_HUMAN (P31152 ) MK04_MOUSE (Q6P5G0)
MAPK6 MK06_HUMAN (Q16659 ) MK06_MOUSE (Q61532)
MAPK7 MK07_HUMAN (Q13164 ) MK07_MOUSE (Q9WVS8)
MAPK8 MK08_HUMAN (P45983 ) MK08_MOUSE (Q91Y86)
MAPK9 MK09_HUMAN (P45984 ) MK09_MOUSE (Q9WTU6)
MOK MOK_HUMAN(Q9UQ07)MOK_MOUSE(Q9WVS4)
NLK NLK_HUMAN(Q9UBE8)NLK_MOUSE(O54949)
PRPF4B PRP4B_HUMAN (Q13523 ) PRP4B_MOUSE (Q61136)
SRPK1 SRPK1_HUMAN (Q96SB4 ) SRPK1_MOUSE (O70551)
SRPK2 SRPK2_HUMAN (P78362 ) SRPK2_MOUSE (O54781)
SRPK3 SRPK3_HUMAN (Q9UPE1 ) SRPK3_MOUSE (Q9Z0G2)
=================================
表1E NEK Ser / Thrプロテインキナーゼファミリー
=================================
NEK1 NEK1_HUMAN (Q96PY6 ) NEK1_MOUSE (P51954)
NEK10 NEK10_HUMAN (Q6ZWH5 ) NEK10_MOUSE (Q3UGM2)
NEK11 NEK11_HUMAN (Q8NG66 ) NEK11_MOUSE (Q8C0Q4)
NEK2 NEK2_HUMAN (P51955 ) NEK2_MOUSE (O35942)
NEK3 NEK3_HUMAN (P51956 ) NEK3_MOUSE (Q9R0A5)
NEK4 NEK4_HUMAN (P51957 ) NEK4_MOUSE (Q9Z1J2)
NEK5 NEK5_HUMAN (Q6P3R8 ) NEK5_MOUSE (Q7TSC3)
NEK6 NEK6_HUMAN (Q9HC98 ) NEK6_MOUSE (Q9ES70)
NEK7 NEK7_HUMAN (Q8TDX7 ) NEK7_MOUSE (Q9ES74)
NEK8 NEK8_HUMAN (Q86SG6 ) NEK8_MOUSE (Q91ZR4)
NEK9 NEK9_HUMAN (Q8TD19 ) NEK9_MOUSE (Q8K1R7)
=================================
表1FSTE Ser / Thrプロテインキナーゼファミリー
=================================
MAP2K1 MP2K1_HUMAN (Q02750 ) MP2K1_MOUSE (P31938)
MAP2K2 MP2K2_HUMAN (P36507 ) MP2K2_MOUSE (Q63932)
MAP2K3 MP2K3_HUMAN (P46734 ) MP2K3_MOUSE (O09110)
MAP2K4 MP2K4_HUMAN (P45985 ) MP2K4_MOUSE (P47809)
MAP2K5 MP2K5_HUMAN (Q13163 ) MP2K5_MOUSE (Q9WVS7)
MAP2K6 MP2K6_HUMAN (P52564 ) MP2K6_MOUSE (P70236)
MAP2K7 MP2K7_HUMAN (O14733 ) MP2K7_MOUSE (Q8CE90)
MAP3K1 M3K1_HUMAN (Q13233 ) M3K1_MOUSE (P53349)
MAP3K10 M3K10_HUMAN (Q02779 ) M3K10_MOUSE (Q66L42)
MAP3K11 M3K11_HUMAN (Q16584 ) M3K11_MOUSE (Q80XI6)
MAP3K12 M3K12_HUMAN (Q12852 ) M3K12_MOUSE (Q60700)
MAP3K13 M3K13_HUMAN (O43283 ) M3K13_MOUSE (Q1HKZ5)
MAP3K14 M3K14_HUMAN (Q99558 ) M3K14_MOUSE (Q9WUL6)
MAP3K15 M3K15_HUMAN (Q6ZN16 ) M3K15_MOUSE (A2AQW0)
MAP3K19 M3K19_HUMAN (Q56UN5 ) M3K19_MOUSE (E9Q3S4)
MAP3K2 M3K2_HUMAN (Q9Y2U5 ) M3K2_MOUSE (Q61083)
MAP3K20 M3K20_HUMAN (Q9NYL2 ) M3K20_MOUSE (Q9ESL4)
MAP3K21 M3K21_HUMAN (Q5TCX8 ) M3K21_MOUSE (Q8VDG6)
MAP3K3 M3K3_HUMAN (Q99759 ) M3K3_MOUSE (Q61084)
MAP3K4 M3K4_HUMAN (Q9Y6R4 ) M3K4_MOUSE (O08648)
MAP3K5 M3K5_HUMAN (Q99683 ) M3K5_MOUSE (O35099)
MAP3K6 M3K6_HUMAN (O95382 ) M3K6_MOUSE (Q9WTR2)
MAP3K7 M3K7_HUMAN (O43318 ) M3K7_MOUSE (Q62073)
MAP3K8 M3K8_HUMAN (P41279 ) M3K8_MOUSE (Q07174)
MAP3K9 M3K9_HUMAN (P80192 ) M3K9_MOUSE (Q3U1V8)
MAP4K1 M4K1_HUMAN (Q92918 ) M4K1_MOUSE (P70218)
MAP4K2 M4K2_HUMAN (Q12851 ) M4K2_MOUSE (Q61161)
MAP4K3 M4K3_HUMAN (Q8IVH8 ) M4K3_MOUSE (Q99JP0)
MAP4K4 M4K4_HUMAN (O95819 ) M4K4_MOUSE (P97820)
MAP4K5 M4K5_HUMAN (Q9Y4K4 ) M4K5_MOUSE (Q8BPM2)
MINK1 MINK1_HUMAN (Q8N4C8 ) MINK1_MOUSE (Q9JM52)
MYO3A MYO3A_HUMAN (Q8NEV4 ) MYO3A_MOUSE (Q8K3H5)
MYO3B MYO3B_HUMAN (Q8WXR4 ) MYO3B_MOUSE (Q1EG27)
NRK NRK_HUMAN(Q7Z2Y5)NRK_MOUSE(Q9R0G8)
OXSR1 OXSR1_HUMAN (O95747 ) OXSR1_MOUSE (Q6P9R2)
PAK1 PAK1_HUMAN (Q13153 ) PAK1_MOUSE (O88643)
PAK2 PAK2_HUMAN (Q13177 ) PAK2_MOUSE (Q8CIN4)
PAK3 PAK3_HUMAN (O75914 ) PAK3_MOUSE (Q61036)
PAK4 PAK4_HUMAN (O96013 ) PAK4_MOUSE (Q8BTW9)
PAK5 PAK5_HUMAN (Q9P286 ) PAK5_MOUSE (Q8C015)
PAK6 PAK6_HUMAN (Q9NQU5 ) PAK6_MOUSE (Q3ULB5)
PBK TOPK_HUMAN(Q96KB5)TOPK_MOUSE(Q9JJ78)
SLK SLK_HUMAN(Q9H2G2)SLK_MOUSE(O54988)
STK10 STK10_HUMAN (O94804 ) STK10_MOUSE (O55098)
STK24 STK24_HUMAN (Q9Y6E0 ) STK24_MOUSE (Q99KH8)
STK25 STK25_HUMAN (O00506 ) STK25_MOUSE (Q9Z2W1)
STK26 STK26_HUMAN (Q9P289 ) STK26_MOUSE (Q99JT2)
STK3 STK3_HUMAN (Q13188 ) STK3_MOUSE (Q9JI10)
STK39 STK39_HUMAN (Q9UEW8 ) STK39_MOUSE (Q9Z1W9)
STK4 STK4_HUMAN (Q13043 ) STK4_MOUSE (Q9JI11)
STRADA STRAA_HUMAN(Q7RTN6)STRAA_MOUSE(Q3UUJ4)
STRADB STRAB_HUMAN(Q9C0K7)STRAB_MOUSE(Q8K4T3)
TAOK1 TAOK1_HUMAN (Q7L7X3 ) TAOK1_MOUSE (Q5F2E8)
TAOK2 TAOK2_HUMAN (Q9UL54 ) TAOK2_MOUSE (Q6ZQ29)
TAOK3 TAOK3_HUMAN (Q9H2K8 ) TAOK3_MOUSE (Q8BYC6)
TNIK TNIK_HUMAN(Q9UKE5)TNIK_MOUSE(P83510)
=================================
表1G TKL Ser / Thrプロテインキナーゼファミリー
=================================
ACVR1 ACVR1_HUMAN (Q04771 ) ACVR1_MOUSE (P37172)
ACVR1B ACV1B_HUMAN (P36896 ) ACV1B_MOUSE (Q61271)
ACVR1C ACV1C_HUMAN (Q8NER5 ) ACV1C_MOUSE (Q8K348)
ACVR2A AVR2A_HUMAN (P27037 ) AVR2A_MOUSE (P27038)
ACVR2B AVR2B_HUMAN (Q13705 ) AVR2B_MOUSE (P27040)
ACVRL1 ACVL1_HUMAN (P37023 ) ACVL1_MOUSE (Q61288)
AMHR2 AMHR2_HUMAN (Q16671 ) AMHR2_MOUSE (Q8K592)
ANKK1 ANKK1_HUMAN (Q8NFD2 ) ANKK1_MOUSE (Q8BZ25)
ARAF ARAF_HUMAN(P10398)ARAF_MOUSE(P04627)
BMPR1A BMR1A_HUMAN (P36894 ) BMR1A_MOUSE (P36895)
BMPR1B BMR1B_HUMAN (O00238 ) BMR1B_MOUSE (P36898)
BMPR2 BMPR2_HUMAN (Q13873 ) BMPR2_MOUSE (O35607)
BRAF BRAF_HUMAN(P15056)BRAF_MOUSE(P28028)
ILK ILK_HUMAN(Q13418)ILK_MOUSE(O55222)
IRAK1 IRAK1_HUMAN (P51617 ) IRAK1_MOUSE (Q62406)
IRAK2 IRAK2_HUMAN (O43187 ) IRAK2_MOUSE (Q8CFA1)
IRAK3 IRAK3_HUMAN (Q9Y616 ) IRAK3_MOUSE (Q8K4B2)
IRAK4 IRAK4_HUMAN (Q9NWZ3 ) IRAK4_MOUSE (Q8R4K2)
KSR1 KSR1_HUMAN (Q8IVT5 ) KSR1_MOUSE (Q61097)
KSR2 KSR2_HUMAN (Q6VAB6 ) KSR2_MOUSE (Q3UVC0)
LIMK1 LIMK1_HUMAN (P53667 ) LIMK1_MOUSE (P53668)
LIMK2 LIMK2_HUMAN (P53671 ) LIMK2_MOUSE (O54785)
LRRK1 LRRK1_HUMAN (Q38SD2 ) LRRK1_MOUSE (Q3UHC2)
LRRK2 LRRK2_HUMAN (Q5S007 ) LRRK2_MOUSE (Q5S006)
RAF1 RAF1_HUMAN (P04049 ) RAF1_MOUSE (Q99N57)
RIPK1 RIPK1_HUMAN (Q13546 ) RIPK1_MOUSE (Q60855)
RIPK2 RIPK2_HUMAN (O43353 ) RIPK2_MOUSE (P58801)
RIPK3 RIPK3_HUMAN (Q9Y572 ) RIPK3_MOUSE (Q9QZL0)
RIPK4 RIPK4_HUMAN (P57078 ) RIPK4_MOUSE (Q9ERK0)
TESK1 TESK1_HUMAN (Q15569 ) TESK1_MOUSE (O70146)
TESK2 TESK2_HUMAN (Q96S53 ) TESK2_MOUSE (Q8VCT9)
TGFBR1 TGFR1_HUMAN (P36897 ) TGFR1_MOUSE (Q64729)
TGFBR2 TGFR2_HUMAN (P37173 ) TGFR2_MOUSE (Q62312)
TNNI3K TNI3K_HUMAN (Q59H18 ) TNI3K_MOUSE (Q5GIG6)
=========================
表1H Tyrプロテインキナーゼファミリー
=========================
AATK LMTK1_HUMAN(Q6ZMQ8)LMTK1_MOUSE(Q80YE4)
ABL1 ABL1_HUMAN (P00519 ) ABL1_MOUSE (P00520)
ABL2 ABL2_HUMAN (P42684 ) ABL2_MOUSE (Q4JIM5)
ALK ALK_HUMAN(Q9UM73)ALK_MOUSE(P97793)
AXL UFO_HUMAN(P30530)UFO_MOUSE(Q00993)
BLK BLK_HUMAN(P51451)BLK_MOUSE(P16277)
BMX BMX_HUMAN(P51813)BMX_MOUSE(P97504)
BTK BTK_HUMAN(Q06187)BTK_MOUSE(P35991)
CSF1R CSF1R_HUMAN (P07333 ) CSF1R_MOUSE (P09581)
CSK CSK_HUMAN(P41240)CSK_MOUSE(P41241)
DDR1 DDR1_HUMAN (Q08345 ) DDR1_MOUSE (Q03146)
DDR2 DDR2_HUMAN (Q16832 ) DDR2_MOUSE (Q62371)
EGFR EGFR_HUMAN(P00533)EGFR_MOUSE(Q01279)
EPHA1 EPHA1_HUMAN (P21709 ) EPHA1_MOUSE (Q60750)
EPHA10 EPHAA_HUMAN(Q5JZY3)EPHAA_MOUSE(Q8BYG9)
EPHA2 EPHA2_HUMAN (P29317 ) EPHA2_MOUSE (Q03145)
EPHA3 EPHA3_HUMAN (P29320 ) EPHA3_MOUSE (P29319)
EPHA4 EPHA4_HUMAN (P54764 ) EPHA4_MOUSE (Q03137)
EPHA5 EPHA5_HUMAN (P54756 ) EPHA5_MOUSE (Q60629)
EPHA6 EPHA6_HUMAN (Q9UF33 ) EPHA6_MOUSE (Q62413)
EPHA7 EPHA7_HUMAN (Q15375 ) EPHA7_MOUSE (Q61772)
EPHA8 EPHA8_HUMAN (P29322 ) EPHA8_MOUSE (O09127)
EPHB1 EPHB1_HUMAN (P54762 ) EPHB1_MOUSE (Q8CBF3)
EPHB2 EPHB2_HUMAN (P29323 ) EPHB2_MOUSE (P54763)
EPHB3 EPHB3_HUMAN (P54753 ) EPHB3_MOUSE (P54754)
EPHB4 EPHB4_HUMAN (P54760 ) EPHB4_MOUSE (P54761)
EPHB6 EPHB6_HUMAN (O15197 ) EPHB6_MOUSE (O08644)
ERBB2 ERBB2_HUMAN (P04626 ) ERBB2_MOUSE (P70424)
ERBB3 ERBB3_HUMAN (P21860 ) ERBB3_MOUSE (Q61526)
ERBB4 ERBB4_HUMAN (Q15303 ) ERBB4_MOUSE (Q61527)
FER FER_HUMAN(P16591)FER_MOUSE(P70451)
FES FES_HUMAN(P07332)FES_MOUSE(P16879)
FGFR1 FGFR1_HUMAN (P11362 ) FGFR1_MOUSE (P16092)
FGFR2 FGFR2_HUMAN (P21802 ) FGFR2_MOUSE (P21803)
FGFR3 FGFR3_HUMAN (P22607 ) FGFR3_MOUSE (Q61851)
FGFR4 FGFR4_HUMAN (P22455 ) FGFR4_MOUSE (Q03142)
FGR FGR_HUMAN(P09769)FGR_MOUSE(P14234)
FLT1 VGFR1_HUMAN (P17948 ) VGFR1_MOUSE (P35969)
FLT3 FLT3_HUMAN (P36888 ) FLT3_MOUSE (Q00342)
FLT4 VGFR3_HUMAN (P35916 ) VGFR3_MOUSE (P35917)
FRK FRK_HUMAN(P42685)FRK_MOUSE(Q922K9)
FYN FYN_HUMAN(P06241)FYN_MOUSE(P39688)
HCK HCK_HUMAN(P08631)HCK_MOUSE(P08103)
IGF1R IGF1R_HUMAN (P08069 ) IGF1R_MOUSE (Q60751)
INSR INSR_HUMAN(P06213)INSR_MOUSE(P15208)
INSRR INSRR_HUMAN(P14616)INSRR_MOUSE(Q9WTL4)
ITK ITK_HUMAN(Q08881)ITK_MOUSE(Q03526)
JAK1 JAK1_HUMAN (P23458 ) JAK1_MOUSE (P52332)
JAK2 JAK2_HUMAN (O60674 ) JAK2_MOUSE (Q62120)
JAK3 JAK3_HUMAN (P52333 ) JAK3_MOUSE (Q62137)
KDR VGFR2_HUMAN(P35968)VGFR2_MOUSE(P35918)
KIT KIT_HUMAN(P10721)KIT_MOUSE(P05532)
LCK LCK_HUMAN(P06239)LCK_MOUSE(P06240)
LMTK2 LMTK2_HUMAN (Q8IWU2 ) LMTK2_MOUSE (Q3TYD6)
LMTK3 LMTK3_HUMAN (Q96Q04 ) LMTK3_MOUSE (Q5XJV6)
LTK LTK_HUMAN(P29376)LTK_MOUSE(P08923)
LYN LYN_HUMAN(P07948)LYN_MOUSE(P25911)
MATK MATK_HUMAN(P42679)MATK_MOUSE(P41242)
MERTK MERTK_HUMAN(Q12866)MERTK_MOUSE(Q60805)
MET MET_HUMAN(P08581)MET_MOUSE(P16056)
MST1R RON_HUMAN(Q04912)RON_MOUSE(Q62190)
MUSK MUSK_HUMAN(O15146)MUSK_MOUSE(Q61006)
NTRK1 NTRK1_HUMAN (P04629 ) NTRK1_MOUSE (Q3UFB7)
NTRK2 NTRK2_HUMAN (Q16620 ) NTRK2_MOUSE (P15209)
NTRK3 NTRK3_HUMAN (Q16288 ) NTRK3_MOUSE (Q6VNS1)
PDGFRA PGFRA_HUMAN(P16234)PGFRA_MOUSE(P26618)
PDGFRB PGFRB_HUMAN(P09619)PGFRB_MOUSE(P05622)
PTK2 FAK1_HUMAN (Q05397 ) FAK1_MOUSE (P34152)
PTK2B FAK2_HUMAN (Q14289 ) FAK2_MOUSE (Q9QVP9)
PTK6 PTK6_HUMAN (Q13882 ) PTK6_MOUSE (Q64434)
PTK7 PTK7_HUMAN (Q13308 ) PTK7_MOUSE (Q8BKG3)
RET RET_HUMAN(P07949)RET_MOUSE(P35546)
ROR1 ROR1_HUMAN (Q01973 ) ROR1_MOUSE (Q9Z139)
ROR2 ROR2_HUMAN (Q01974 ) ROR2_MOUSE (Q9Z138)
ROS1 ROS1_HUMAN (P08922 ) ROS1_MOUSE (Q78DX7)
RYK RYK_HUMAN(P34925)RYK_MOUSE(Q01887)
SRC SRC_HUMAN(P12931)SRC_MOUSE(P05480)
SRMS SRMS_HUMAN(Q9H3Y6)SRMS_MOUSE(Q62270)
STYK1 STYK1_HUMAN (Q6J9G0 ) STYK1_MOUSE (Q6J9G1)
SYK KSYK_HUMAN(P43405)KSYK_MOUSE(P48025)
Smok1 SMOK1_MOUSE (Q9QYZ4)
Smoktcr SMKTR_MOUSE(A2KF29)
TEC TEC_HUMAN(P42680)TEC_MOUSE(P24604)
TEK TIE2_HUMAN(Q02763)TIE2_MOUSE(Q02858)
TIE1 TIE1_HUMAN (P35590 ) TIE1_MOUSE (Q06806)
TNK1 TNK1_HUMAN (Q13470 ) TNK1_MOUSE (Q99ML2)
TNK2 ACK1_HUMAN (Q07912 ) ACK1_MOUSE (O54967)
TXK TXK_HUMAN(P42681)TXK_MOUSE(P42682)
TYK2 TYK2_HUMAN (P29597 ) TYK2_MOUSE (Q9R117)
TYRO3 TYRO3_HUMAN (Q06418 ) TYRO3_MOUSE (P55144)
YES1 YES_HUMAN(P07947)YES_MOUSE(Q04736)
ZAP70 ZAP70_HUMAN (P43403 ) ZAP70_MOUSE (P43404)
=====
表1I その他のキナーゼ
=====
AAK1 AAK1_HUMAN (Q2M2I8 ) AAK1_MOUSE (Q3UHJ0)
AURKA AURKA_HUMAN(O14965)AURKA_MOUSE(P97477)
AURKB AURKB_HUMAN(Q96GD4)AURKB_MOUSE(O70126)
AURKC AURKC_HUMAN(Q9UQB9)AURKC_MOUSE(O88445)
BMP2K BMP2K_HUMAN (Q9NSY1 ) BMP2K_MOUSE (Q91Z96)
BUB1 BUB1_HUMAN (O43683 ) BUB1_MOUSE (O08901)
BUB1B BUB1B_HUMAN (O60566 ) BUB1B_MOUSE (Q9Z1S0)
CAMKK1 KKCC1_HUMAN (Q8N5S9 ) KKCC1_MOUSE (Q8VBY2)
CAMKK2 KKCC2_HUMAN (Q96RR4 ) KKCC2_MOUSE (Q8C078)
CDC7 CDC7_HUMAN (O00311 ) CDC7_MOUSE (Q9Z0H0)
CHUK IKKA_HUMAN(O15111)IKKA_MOUSE(Q60680)
CSNK2A1 CSK21_HUMAN (P68400 ) CSK21_MOUSE (Q60737)
CSNK2A2 CSK22_HUMAN (P19784 ) CSK22_MOUSE (O54833)
CSNK2A3 CSK23_HUMAN (Q8NEV1 )
DSTYK DUSTY_HUMAN(Q6XUX3)DUSTY_MOUSE(Q6XUX1)
EIF2AK1 E2AK1_HUMAN (Q9BQI3 ) E2AK1_MOUSE (Q9Z2R9)
EIF2AK2 E2AK2_HUMAN (P19525 ) E2AK2_MOUSE (Q03963)
EIF2AK3 E2AK3_HUMAN (Q9NZJ5 ) E2AK3_MOUSE (Q9Z2B5)
EIF2AK4 E2AK4_HUMAN (Q9P2K8 ) E2AK4_MOUSE (Q9QZ05)
ERN1 ERN1_HUMAN (O75460 ) ERN1_MOUSE (Q9EQY0)
ERN2 ERN2_HUMAN (Q76MJ5 ) ERN2_MOUSE (Q9Z2E3)
GAK GAK_HUMAN(O14976)GAK_MOUSE(Q99KY4)
HASPIN HASP_HUMAN(Q8TF76)HASP_MOUSE(Q9Z0R0)
IKBKB IKKB_HUMAN(O14920)IKKB_MOUSE(O88351)
IKBKE IKKE_HUMAN(Q14164)IKKE_MOUSE(Q9R0T8)
MLKL MLKL_HUMAN(Q8NB16)MLKL_MOUSE(Q9D2Y4)
MOS MOS_HUMAN(P00540)MOS_MOUSE(P00536)
NRBP1 NRBP_HUMAN(Q9UHY1)NRBP_MOUSE(Q99J45)
NRBP2 NRBP2_HUMAN (Q9NSY0 ) NRBP2_MOUSE (Q91V36)
PAN3 PAN3_HUMAN (Q58A45 ) PAN3_MOUSE (Q640Q5)
PDIK1L PDK1L_HUMAN (Q8N165 ) PDK1L_MOUSE (Q8QZR7)
PEAK1 PEAK1_HUMAN (Q9H792 ) PEAK1_MOUSE (Q69Z38)
PIK3R4 PI3R4_HUMAN (Q99570 ) PI3R4_MOUSE (Q8VD65)
PINK1 PINK1_HUMAN (Q9BXM7 ) PINK1_MOUSE (Q99MQ3)
PKDCC PKDCC_HUMAN(Q504Y2)PKDCC_MOUSE(Q5RJI4)
PKMYT1 PMYT1_HUMAN (Q99640 ) PMYT1_MOUSE (Q9ESG9)
PLK1 PLK1_HUMAN (P53350 ) PLK1_MOUSE (Q07832)
PLK2 PLK2_HUMAN (Q9NYY3 ) PLK2_MOUSE (P53351)
PLK3 PLK3_HUMAN (Q9H4B4 ) PLK3_MOUSE (Q60806)
PLK4 PLK4_HUMAN (O00444 ) PLK4_MOUSE (Q64702)
PLK5 PLK5_HUMAN (Q496M5 ) PLK5_MOUSE (Q4FZD7)
POMK SG196_HUMAN(Q9H5K3)SG196_MOUSE(Q3TUA9)
PRAG1 PRAG1_HUMAN (Q86YV5 ) PRAG1_MOUSE (Q571I4)
PXK PXK_HUMAN(Q7Z7A4)PXK_MOUSE(Q8BX57)
RNASEL RN5A_HUMAN(Q05823)RN5A_MOUSE(Q05921)
RPS6KC1 KS6C1_HUMAN (Q96S38 ) KS6C1_MOUSE (Q8BLK9)
RPS6KL1 RPKL1_HUMAN (Q9Y6S9 ) RPKL1_MOUSE (Q8R2S1)
SBK1 SBK1_HUMAN (Q52WX2 ) SBK1_MOUSE (Q8QZX0)
SBK2 SBK2_HUMAN (P0C263 ) SBK2_MOUSE (P0C5K1)
SBK3 SBK3_HUMAN (P0C264 ) SBK3_MOUSE (P0C5K0)
SCYL1 SCYL1_HUMAN (Q96KG9 ) SCYL1_MOUSE (Q9EQC5)
SCYL2 SCYL2_HUMAN (Q6P3W7 ) SCYL2_MOUSE (Q8CFE4)
SCYL3 PACE1_HUMAN (Q8IZE3 ) PACE1_MOUSE (Q9DBQ7)
SGK494 SG494_HUMAN (Q96LW2 ) SG494_MOUSE (Q5SYL1)
STK16 STK16_HUMAN (O75716 ) STK16_MOUSE (O88697)
STK31 STK31_HUMAN (Q9BXU1 ) STK31_MOUSE (Q99MW1)
STK32A ST32A_HUMAN (Q8WU08 ) ST32A_MOUSE (Q8BGW6)
STK32B ST32B_HUMAN (Q9NY57 ) ST32B_MOUSE (Q9JJX8)
STK32C ST32C_HUMAN (Q86UX6 ) ST32C_MOUSE (Q8QZV4)
STK35 STK35_HUMAN (Q8TDR2 ) STK35_MOUSE (Q80ZW0)
STK36 STK36_HUMAN (Q9NRP7 ) STK36_MOUSE (Q69ZM6)
STKLD1 STKL1_HUMAN (Q8NE28 ) STKL1_MOUSE (Q80YS9)
TBCK TBCK_HUMAN(Q8TEA7)TBCK_MOUSE(Q8BM85)
TBK1 TBK1_HUMAN (Q9UHD2 ) TBK1_MOUSE (Q9WUN2)
TEX14 TEX14_HUMAN (Q8IWB6 ) TEX14_MOUSE (Q7M6U3)
TLK1 TLK1_HUMAN (Q9UKI8 ) TLK1_MOUSE (Q8C0V0)
TLK2 TLK2_HUMAN (Q86UE8 ) TLK2_MOUSE (O55047)
TP53RK PRPK_HUMAN(Q96S44)PRPK_MOUSE(Q99PW4)
TTK TTK_HUMAN(P33981)TTK_MOUSE(P35761)
UHMK1 UHMK1_HUMAN (Q8TAS1 ) UHMK1_MOUSE (P97343)
ULK1 ULK1_HUMAN (O75385 ) ULK1_MOUSE (O70405)
ULK2 ULK2_HUMAN (Q8IYT8 ) ULK2_MOUSE (Q9QY01)
ULK3 ULK3_HUMAN (Q6PHR2 ) ULK3_MOUSE (Q3U3Q1)
ULK4 ULK4_HUMAN (Q96C45 ) ULK4_MOUSE (Q3V129)
WEE1 WEE1_HUMAN (P30291 ) WEE1_MOUSE (P47810)
WEE2 WEE2_HUMAN (P0C1S8 ) WEE2_MOUSE (Q66JT0)
WNK1 WNK1_HUMAN (Q9H4A3 ) WNK1_MOUSE (P83741)
WNK2 WNK2_HUMAN (Q9Y3S1 ) WNK2_MOUSE (Q3UH66)
WNK3 WNK3_HUMAN (Q9BYP7 ) WNK3_MOUSE (Q80XP9)
WNK4 WNK4_HUMAN (Q96J92 ) WNK4_MOUSE (Q80UE6)
====================================
表1J. ADCKプロテインキナーゼファミリー
====================================
ADCK1 ADCK1_HUMAN (Q86TW2 ) ADCK1_MOUSE (Q9D0L4)
ADCK2 ADCK2_HUMAN (Q7Z695 ) ADCK2_MOUSE (Q6NSR3)
ADCK5 ADCK5_HUMAN (Q3MIX3 ) ADCK5_MOUSE (Q80V03)
COQ8A COQ8A_HUMAN (Q8NI60 ) COQ8A_MOUSE (Q60936)
COQ8B COQ8B_HUMAN (Q96D53 ) COQ8B_MOUSE (Q566J8)
==========================================
表1K.アルファ型プロテインキナーゼファミリー
==========================================
ALPK1 ALPK1_HUMAN (Q96QP1 ) ALPK1_MOUSE (Q9CXB8)
ALPK2 ALPK2_HUMAN (Q86TB3 ) ALPK2_MOUSE (Q91ZB0)
ALPK3 ALPK3_HUMAN (Q96L96 ) ALPK3_MOUSE (Q924C5)
EEF2K EF2K_HUMAN (O00418 ) EF2K_MOUSE (O08796)
TRPM6 TRPM6_HUMAN (Q9BX84 ) TRPM6_MOUSE (Q8CIR4)
TRPM7 TRPM7_HUMAN (Q96QT4 ) TRPM7_MOUSE (Q923J1)
====================================
表1L.FASTプロテインキナーゼファミリー
====================================
FASTK FASTK_HUMAN(Q14296)FASTK_MOUSE(Q9JIX9)
=========================================
表1M.PDK / BCKDKプロテインキナーゼファミリー
=========================================
BCKDK BCKD_HUMAN(O14874)BCKD_MOUSE(O55028)
PDK1 PDK1_HUMAN (Q15118 ) PDK1_MOUSE (Q8BFP9)
PDK2 PDK2_HUMAN (Q15119 ) PDK2_MOUSE (Q9JK42)
PDK3 PDK3_HUMAN (Q15120 ) PDK3_MOUSE (Q922H2)
PDK4 PDK4_HUMAN (Q16654 ) PDK4_MOUSE (O70571)
===============================
表1N.PI3 / PI4-キナーゼファミリー
===============================
ATM ATM_HUMAN(Q13315)ATM_MOUSE(Q62388)
ATR ATR_HUMAN(Q13535)ATR_MOUSE(Q9JKK8)
MTOR MTOR_HUMAN(P42345)MTOR_MOUSE(Q9JLN9)
PIK3CA PK3CA_HUMAN (P42336 ) PK3CA_MOUSE (P42337)
PIK3CG PK3CG_HUMAN (P48736 ) PK3CG_MOUSE (Q9JHG7)
PRKDC PRKDC_HUMAN(P78527)PRKDC_MOUSE(P97313)
SMG1 SMG1_HUMAN (Q96Q15 ) SMG1_MOUSE (Q8BKX6)
========================================
表1O.RIO型Ser / Thrキナーゼファミリー
========================================
RIOK1 RIOK1_HUMAN (Q9BRS2 ) RIOK1_MOUSE (Q922Q2)
RIOK2 RIOK2_HUMAN (Q9BVS4 ) RIOK2_MOUSE (Q9CQS5)
RIOK3 RIOK3_HUMAN (O14730 ) RIOK3_MOUSE (Q9DBU3)
すべての出発物質及び試薬は商業的供給元から購入し、特に断らない限り、受け取ったままの状態で使用した。以下の実施例で使用される略語は次のとおりである。Bocはtert-ブチルオキシカルボニルであり、DCMはジクロロメタンであり、DMFはN,N-ジメチルホルムアミドであり、ESIはエレクトロスプレーイオン化であり、HATUは1-[ビス(ジメチルアミノ)メチレン]-1H-1,2,3-トリアゾロ[4,5-b]ピリジニウム-3-オキシドヘキサフルオロホスフェートであり、HPLCは高速液体クロマトグラフィーであり、MSは質量分析であり、RTは室温であり、TFAはトリフルオロ酢酸である。
Tert-ブチル(15-(4-(4-((5-クロロ-4-((2-(メチルカルバモイル)フェニル)アミノ)ピリミジン-2-イル)アミノ)フェニル)ピペラジン-1-イル)-15-オキソ-3,6,9,12-テトラオキサペンタデシル)カルバメート
化合物CC-1290
2-((5-クロロ-2-((4-(ピペラジン-1-イル)フェニル)アミノ)ピリミジン-4-イル)アミノ)-N-メチルベンズアミド(200.0mg、0.46mmol)及び2,2-ジメチル-4-オキソ-3,8,11,14,17-ペンタオキサ-5-アザイコサン-20-酸(250.0mg、0.69mmol)及びHATU(208.4mg、0.55mmol)をDMF(5mL)に取り込み、N,N-ジイソプロピルエチルアミン(238.7μL、1.37mmol)を加えた。混合物を3時間撹拌し、揮発性物質を減圧下で除去した。粗生成物を最小量のジクロロメタンに取り、セライトに吸収させ、そして自由流動性の固体となるまで乾燥させた。混合物をシリカゲルフラッシュクロマトグラフィーに供して所望の生成物(192.0mg、53.3%)を白色固体として得た。[M+H]+C38H54ClN8O8のMS(ESI+)m/z計算値785.38、実測値785.60。
化合物CC-1294
Tert-ブチル(15-(4-(4-((5-クロロ-4-((2-(メチルカルバモイル)フェニル)アミノ)ピリミジン-2-イル)アミノ)フェニル)ピペラジン-1-イル)-15-オキソ-3,6,9,12-テトラオキサペンタデシル)カルバメート(125.0mg、0.16mmol)をDCM(2.0mL)に加えた溶液を、100μLのトリイソプロピルシラン、次いでトリフルオロ酢酸(2mL)で処理した。混合物に蓋をし、3時間撹拌し、揮発性物質を減圧下で除去して黄色の油状物を得た。混合物を高真空下で乾燥させ、残留物をジエチルエーテルで処理して黄色の固体を得た。ジエチルエーテルをデカントし、残留物を高真空下で30分間乾燥させた。粗生成物を撹拌しながら無水DMF(5mL)に取り、N、N-ジイソプロピルエチルアミン(277μL、1.59mmol)で処理した。反応液を10分間撹拌し、NanoBRET(商標)590SEトレーサー(Promega Corporation、74.5mg、0.17mmol)を加え、反応液を暗所で2時間撹拌した。揮発性物質を減圧下で除去して青色のフィルムを得、これをアミン修飾シリカゲルフラッシュクロマトグラフィーによって精製して生成物(118.5mg 74.8%)を青色固体として得た。[M+H]+C49H58BClF2N11O7のMS(ESI+)m/z計算値996.46、実測値996.4。
Tert-ブチル(15-(4-(3-アミノフェニル)ピペラジン-1-イル)-15-オキソ-3,6,9,12テトラオキサペンタデシル)カルバメート
化合物CC-1815
2,5-ジオキソピロリジン-1-イル2,2-ジメチル-4-オキソ-3,8,11,14,17-ペンタオキサ-5-アザイコサン-20-オエート(525.0mg、1.14mmol)及び3-(ピペラジン-1-イル)アニリン(200.0mg、1.13mmol)をジクロロメタン(10.0mL)に溶解し、黄色の懸濁液を得た。N,N-ジイソプロピルエチルアミン(590μL、3.39mmol)を加え、混合物を2時間撹拌した。粗混合物をセライトに吸収させ、揮発性物質を減圧下で除去し、粗生成物をシリカゲルフラッシュクロマトグラフィーに供して生成物(590.0mg、100%)を黄色の固体として得た。
2-((2-((3-(4-(1-アミノ-3,6,9,12-テトラオキサペンタデカン-15-オイル)ピペラジン-1-イル)フェニル)アミノ)-5-クロロピリミジン-4-イル)アミノ)ベンズアミド
化合物CC-1816
2-((2,5-ジクロロピリミジン-4-イル)アミノ)ベンズアミド(294.3mg、1.04mmol)及びtert-ブチル(15-(4-(3-アミノフェニル)ピペラジン-1-イル)-15-オキソ-3,6,9,12-テトラオキサペンタデシル)カルバメート(600.0mg、1.14mmol)を2-メトキシエタノール(8mL)に加えた溶液を100℃に一晩加熱した。混合物を室温に冷却し、揮発性物質を減圧下で除去して、赤色の固体を得て、これを高真空下で乾燥させた。Bocを脱保護した粗残留物を最小量のジクロロメタンに溶解し、セライトに吸収させ、自由流動性固体にまで乾燥させ、シリカゲルフラッシュクロマトグラフィーによって精製して所望の生成物(270.0mg、33.7%)を赤黄色固体として得た。[M+H]+C32H44ClN8O6のMS(ESI+)m/z計算値671.31、実測値671.30。
化合物CC-1817
2-((2-((3-(4-(1-アミノ-3,6,9,12-テトラオキサペンタデカン-15-オイル)ピペラジン-1-イル)フェニル)アミノ)-5-クロロピリミジン-4-イル)アミノ)ベンズアミド(250.0mg、0.037mmol)を無水DMF(5mL)に攪拌しながら取り込んだ。混合物に、N,N-ジイソプロピルエチルアミン(22.2μL、0.03mmol)を加え、反応物を10分間撹拌した。NanoBRET(商標)590SEトレーサー(PromegaCorp.、17.5mg、0.038mmol)を加え、反応物を暗所で2時間撹拌した。揮発性物質を減圧下で除去して青色のフィルムを得、これを8mLの1:1:0.01のアセトニトリル、水、トリフルオロ酢酸に取り、逆相分取HPLC精製に供して生成物(12.0mg 32.8%)を青色固体として得た。[M+H]+C48H56BClF2N11O7のMS(ESI+)m/z計算値982.41、実測値982.67。
Tert-ブチル 4-(4-((4-((2-カルバモイルフェニル)アミノ)-5-クロロピリミジン-2-イル)アミノ)フェニル)ピペラジン-1-カルボキシレート
化合物CC-1790
2-((2,5-ジクロロピリミジン-4-イル)アミノ)ベンズアミド(500mg、1.77mmol)及びtert-ブチル 4-(4-アミノフェニル)ピペラジン-1-カルボキシレート(583.8、1.94mmol)を2-メトキシエタノール(6mL)に加えた溶液を100℃に一晩加熱した。混合物を室温に冷却し、揮発性物質を減圧下で除去して褐色の固体を得、これを高真空下で乾燥させた。粗残留物を最小量のジクロロメタンに溶解し、セライトに吸収させ、そして自由流動性の固体に乾燥させた。混合物をシリカゲルフラッシュクロマトグラフィーにより精製して所望の生成物(200.0mg、21.6%)を黄色固体として得た。[M+H]+C26H31ClN7O3のMS(ESI+)m/z計算値524.22、実測値524.19。
2-((5-クロロ-2-((4-(ピペラジン-1-イル)フェニル)アミノ)ピリミジン-4-イル)アミノ)ベンズアミド-TFA
化合物CC-1795
Tert-ブチル4-(4-((4-((2-カルバモイルフェニル)アミノ)-5-クロロピリミジン-2-イル)アミノ)フェニル)ピペラジン-1-カルボキシレート(200.0mg、0.38mmol)をDCM(3.0mL)に加えた溶液を300μLのトリイソプロピルシラン、次いでトリフルオロ酢酸(3mL)で処理した。混合物に蓋をし、4時間撹拌し、揮発性物質を減圧下で除去して紫色の油状物を得た。混合物を高真空下で乾燥させ、残留物をジエチルエーテルで処理して、暗色の固体を得た。エーテルをデカントし、ジエチルエーテルの追加部分を加えてデカントした後、残留物を高真空下で一晩乾燥させた。得られた固体を1:1:0.01のアセトニトリル、水、トリフルオロ酢酸に溶解し、逆相分取HPLC精製に供して所望の生成物(136.0mg、84.1%)を黄色の固体として得た。
tert-ブチル (15-(4-(4-((4-((2-カルバモイルフェニル)アミノ)-5-クロロピリミジン-2-イル)アミノ)フェニル)ピペラジン-1-イル)-15-オキソ-3,6,9,12-テトラオキサペンタデシル)カルバメート
化合物CC-1796
2-((5-クロロ-2-((4-(ピペラジン-1-イル)フェニル)アミノ)ピリミジン-4-イル)アミノ)ベンズアミド(100.0mg、0.24mmol)、2,5-ジオキソピロリジン-1-2,2-ジメチル-4-オキソ-3,8,11,14,17-ペンタオキサ-5-アザイコサン-20-オエート(163.7mg、353.9mmol)及びN,N-ジイソプロピルエチルアミン(127.3μL、0.71mmol)をジクロロメタン(10mL)に加えた溶液を2時間撹拌した。粗生成物をセライトに吸収させ、自由流動性の固体に乾燥させ、混合物をシリカゲルフラッシュクロマトグラフィーに供して、所望の生成物(156.0mg、85.7%)を黄色固体として得た。[M+H]+C37H52ClN8O8のMS(ESI+)m/z計算値771.38、実測値771.35。
2-((2-((4-(4-(1-アミノ-3,6,9,12-テトラオキサペンタデカン-15-オイル)ピペラジン-1-イル)フェニル)アミノ)-5-クロロピリミジン-4-イル)アミノ)ベンズアミド-TFA
化合物CC-1803
tert-ブチル(15-(4-(4-((4-((2-カルバモイルフェニル)アミノ)-5-クロロピリミジン-2-イル)アミノ)フェニル)ピペラジン-1-イル)-15-オキソ-3,6,9,12-テトラオキサペンタデシル)カルバメート(100.0mg、0.13mmol)をDCM(3.0mL)に加えた溶液を300μLのトリイソプロピルシラン、次いでトリフルオロ酢酸(3mL)で処理した。混合物に蓋をして、1時間撹拌した。揮発性物質を減圧下で除去し、混合物を高真空下で乾燥させた。残留物をジエチルエーテルで処理して、赤色の固体を得て、デカントし、ジエチルエーテルの追加部分を加えてデカントした後、残留物を真空下で一晩乾燥させた。得られた固体を1:1:0.01のアセトニトリル、水、トリフルオロ酢酸に溶解し、逆相分取HPLCに供して、所望の生成物(67.9mg、66.7%)を黄色の固体として得た。[M+H]+C32H44ClN8O6MSの(ESI+)m/z計算値671.31、実測値671.35。
化合物CC-1804
2-((2-((4-(4-(1-アミノ-3,6,9,12-テトラオキサペンタデカン-15-オイル)ピペラジン-1-イル)フェニル)アミノ)-5-クロロピリミジン-4-イル)アミノ)ベンズアミド-TFA(20.0mg、0.03mmol)を5mlの無水DMFに攪拌しながら取り込んだ。混合物にN,Nージイソプロピルエチルアミン(22.2μL、0.03mmol)を加え、反応液を10分間撹拌した。NanoBRET(商標)590SEトレーサー(Promega Corp.、16.3mg、0.038mmol)を加え、反応液を暗所で90分間撹拌した。揮発性物質を減圧下で除去して青色のフィルムを得、これを8mLの1:1:0.01のアセトニトリル、水、トリフルオロ酢酸に取り、逆相分取HPLC精製に供して、生成物(24.8mg、99.0%)を青色固体として得た。[M+H]+C48H57BClF2N11O7のMS(ESI+)m/z計算値983.31、実測値983.42。
CC-1294から誘導されたNanoBRET(商標)トレーサーと新規の阻害剤から誘導されたNanoBRET(商標)トレーサーを用いた細胞内キナーゼ標的結合の包括的分析を導くため、本明細書の実施形態を発展させる実験を行った。96ウェルプレートのウェル中、各ウェル当たり20,000個のHEK293細胞にキナーゼ/NanoLuc(登録商標)(Nluc)融合タンパク質を発現させるためのpFN31K及びpFN32Kプラスミドをトランスフェクトした。トランスフェクションは、3:1のFuGENE HD:プラスミド比を用いて行った。トランスフェクションの24時間後に細胞を0.5μMのCC-1804、CC-1852、または1μMのCC-1294の存在下で2時間処理した。インキュベーション後、NanoBRET(登録商標)標的結合(TE)基質/阻害剤溶液を1Xの最終濃度まで加えた。NanoBRETをGlomax(登録商標)Discoverプレートリーダーで測定した。相対BRETシグナルを求めるため、トレーサーから生じたBRETをトレーサーの非存在下のBRETで割った。図1A~Bに示されるように、予想外に広いスペクトルの標的結合/キナーゼプロファイリングが、CC-1294と比較してCC-1804及びCC-1852で観察された。
CC-1294によっては実現されず、CC-1804によって固有に実現される、新規な生細胞標的結合アッセイを実証するため、本明細書の実施形態を発展させる実験を行った。96ウェルプレートのウェル中、各ウェル当たり20,000個のHEK293細胞にキナーゼ/NanoLuc(登録商標)(Nluc)融合タンパク質を発現させるためのpFN31K及びpFN32Kプラスミドをトランスフェクトした。トランスフェクションは、3:1のFuGENE HD:プラスミド比を用いて行った。トランスフェクションの24時間後、細胞を図2A~Cに示される異なる濃度のトレーサー及び異なる濃度のコントロール阻害剤の存在下で2時間処理した。インキュベーション後、NanoBRET(商標)-TE基質/阻害剤溶液を1Xの最終濃度まで加え、BRETをGlomax(登録商標)Discoverプレートリーダーで測定した。
親分子CC-1861とCTx-0294885の広域スペクトルの細胞内キナーゼ標的結合を分析するため、本明細書の実施形態を発展させる実験を行った(図3)。96ウェルプレートのウェル中、各ウェル当たり20,000個のHEK293細胞にpFN31K及びpFN32Kプラスミドから発現されたキナーゼ/Nluc融合タンパク質をトランスフェクトした。トランスフェクションは、3:1のFuGENE HD:プラスミド比を用いて行った。トランスフェクションの24時間後に細胞を試験化合物として300nMのCC-1861、300nMのCTx-0294885、または0.1%DMSO(溶媒)の存在下、最適化した濃度で導入したNanoBRET(商標)トレーサー(K4、K5、K7、K8、K9、K10、K11)の存在下で2時間処理した。分析は、BRET=0(完全な占有率のコントロール試料)を測定するためにタグ付けしていないNlucを用いることでも行った。インキュベーション後、NanoBRET(登録商標)-TE基質/阻害剤溶液を1Xの最終濃度まで加えた。NanoBRETをGlomax(登録商標)Discoverプレートリーダーで測定した。生のBRET比の値を生成するため、アクセプター放射値(例えば、610nm)を各試料のドナー放射値(例えば、450nm)で割った。
占有率(%)=[1-(X-Z)/(Y-Z)]*100
式中、X=試験化合物及びトレーサーの存在下でのBRETであり、Y=トレーサーのみの存在下でのBRET(占有率=0のコントロール)であり、Z=完全占有率コントロールのBRET(すなわち、タグ付けされていないNluc融合タンパク質からのBRET)である。
非改変CC-1861とCTx-0294885のキナーゼ親和性の増加を示すため、本明細書の実施形態を発展させる実験を行った。96ウェルプレートのウェル中、各ウェル当たり20,000個のHEK293細胞にpFN31K及びpFN32Kプラスミドから発現されたキナーゼ/Nluc融合タンパク質をトランスフェクトした。トランスフェクションは、3:1のFuGENE HD:プラスミド比を用いて行った。トランスフェクションの24時間後、細胞を、トレーサー及び示される異なる濃度のコントロール阻害剤の存在下で2時間処理した。インキュベーション後、NanoBRET(商標)-TE基質/阻害剤溶液を1Xの最終濃度まで加え、BRETをGlomax(登録商標)Discoverプレートリーダーで測定した。
2-((5-クロロ-2-((4-(ピペラジン-1-イル)フェニル)アミノ)ピリミジン-4-イル)アミノ)ベンズアミド
化合物CC-1861
DCM(2.0mL)に加えたTert-ブチル 4-(4-((4-((2-カルバモイルフェニル)アミノ)-5-クロロピリミジン-2-イル)アミノ)フェニル)ピペラジン-1-カルボキシレート(90.0mg、0.17mmol)をトリイソプロピルシラン(200μL、0.17mmol)、次いでトリフルオロ酢酸(2.0mL)で処理した。蓋をした混合物を3時間撹拌し、揮発性物質を減圧下で除去して、黄色の油状物を得た。残留物を20mLのジエチルエーテルで処理して、白色の固体を得た。エーテルをデカントし、得られた白色固体を20mLの新鮮なジエチルエーテルで粉砕した。エーテルをデカントし、得られた白色固体を高真空下で20分間乾燥させた。残留物をメタノール(10mL)に溶解し、45mgの炭酸カリウムで処理した。得られた混合物を1時間撹拌し、セライトに吸収させ、DCM中、メタノールの勾配を用いたフラッシュシリカゲルクロマトグラフィーに供した。画分を含む生成物をプールし、濃縮して、生成物(50.0mg、68.7%)を白色固体として得た。[M+H]+C21H22ClN7OのMS(ESI+)m/z計算値:424.17、実測値424.24。
本発明のまた別の態様は、以下のとおりであってもよい。
〔1〕下式の広域スペクトルキナーゼ結合剤。
(CC-1852)
〔2〕下式の広域スペクトルキナーゼ結合剤。
(CC-1861)
〔3〕下式の部分を含む、機能的要素または固体表面に結合された広域スペクトルキナーゼ結合剤:
(前記機能的要素または固体表面に結合されたもの)。
〔4〕下式の部分を含む、機能的要素または固体表面に結合された広域スペクトルキナーゼ結合剤:
(前記機能的要素または固体表面に結合されたもの)。
〔5〕前記固体表面が、沈降粒子、膜、ガラス、チューブ、ウェル、自己組織化単分子層、表面プラズモン共鳴チップ、または電子伝導性表面を備えた固体支持体から選択される、前記〔3〕または〔4〕に記載の広域スペクトルキナーゼ結合剤。
〔6〕前記沈降粒子が、磁性粒子である、前記〔5〕に記載の広域スペクトルキナーゼ結合剤。
〔7〕前記機能的要素が、検出可能な要素、親和性要素、及び捕捉要素から選択される、前記〔3〕または〔4〕に記載の広域スペクトルキナーゼ結合剤。
〔8〕前記検出可能な要素が、フルオロフォア、発色団、放射性核種、電子不透明分子、MRI造影剤、SPECT造影剤、または質量タグを含む、前記〔7〕に記載の広域スペクトルキナーゼ結合剤。
〔9〕CC-1852またはCC-1861が機能的要素に直接結合している、前記〔3〕~〔8〕のいずれか1項に記載の広域スペクトルキナーゼ結合剤。
〔10〕前記CC-1852またはCC-1861がリンカーを介して機能的要素に結合されている、前記〔3〕~〔8〕のいずれか1項に記載の広域スペクトルキナーゼ結合剤。
〔11〕前記リンカーが、-[(CH 2 ) 2 O] n -(式中、nは1~20である)を含む、前記〔10〕に記載の広域スペクトルキナーゼ結合剤。
〔12〕前記リンカーが、アミド結合によってCC-1852またはCC-1861、及び/または機能的要素と結合される、前記〔11〕に記載の広域スペクトルキナーゼ結合剤。
〔13〕下記構造:
(式中、Xは機能的要素または固体表面である)を含む、前記〔3〕~〔8〕及び〔10〕~〔12〕のいずれか1項に記載の広域スペクトルキナーゼ結合剤。
〔14〕Xが、フルオロフォアである、前記〔13〕に記載の広域スペクトルキナーゼ結合剤。
〔15〕下記構造:
を含む、前記〔14〕に記載の広域スペクトルキナーゼ結合剤。
〔16〕下記構造:
(式中、Xは機能的要素または固体表面である)を含む、前記〔3〕~〔4〕及び〔10〕~〔12〕のいずれか1項に記載の広域スペクトルキナーゼ結合剤。
〔17〕Xが、フルオロフォアである、前記〔16〕に記載の広域スペクトルキナーゼ結合剤。
〔18〕下記構造:
を含む、前記〔17〕に記載の広域スペクトルキナーゼ結合剤。
〔19〕非天然存在比の1つ以上の安定した重同位体を含む、前記〔1〕~〔18〕のいずれか1項に記載の広域スペクトルキナーゼ結合剤。
〔20〕前記〔1〕~〔19〕のいずれか1項に記載の広域スペクトルキナーゼ結合剤を含む組成物。
〔21〕試料中のキナーゼを検出または定量化する方法であって、前記試料を前記〔3〕~〔4〕または〔7〕~〔19〕のいずれか1項に記載の組成物と接触させる工程と、それによって生成されたシグナルの前記機能的要素を検出または定量化する工程と、を含む、前記方法。
〔22〕前記それによって生成された信号の機能的要素が、蛍光、質量分析、光学イメージング、磁気共鳴イメージング(MRI)、及びエネルギー転移によって検出または定量化される、前記〔21〕に記載の方法。
〔23〕試料からキナーゼを単離する方法であって、前記試料を前記〔3〕~〔13〕、〔16〕、及び〔19〕のいずれか1項に記載の広域スペクトルキナーゼ結合剤と接触させる工程と、前記固体表面の前記機能的要素及び結合したキナーゼを前記試料の非結合部分から分離する工程と、を含む、前記方法。
〔24〕試料中のキナーゼが何であるかを特徴付ける方法であって、前記〔23〕に記載の方法によって試料からキナーゼを単離する工程と、単離されたキナーゼを質量分析によって分析する工程と、を含む、前記方法。
〔25〕キナーゼと非修飾生体分子との間の相互作用を監視する方法であって、試料を、前記〔3〕~〔13〕、〔16〕、及び〔19〕のいずれか1項に記載の広域スペクトルキナーゼ結合剤と接触させる工程を含む、前記方法。
〔26〕前記試料が、細胞、細胞ライセート、体液、組織、生物学的試料、インビトロ試料、及び環境試料から選択される、前記〔21〕~〔25〕のいずれか1項に記載の方法。
Claims (23)
- 下式の広域スペクトルキナーゼ結合剤。
(CC-1852) - 下式の部分を含む、機能的要素または固体表面に結合された広域スペクトルキナーゼ結合剤:
(前記機能的要素または固体表面に結合されたもの)。 - 前記固体表面が、沈降粒子、膜、ガラス、チューブ、ウェル、自己組織化単分子層、表面プラズモン共鳴チップ、または電子伝導性表面を備えた固体支持体から選択される、請求項2に記載の広域スペクトルキナーゼ結合剤。
- 前記固体表面が沈降粒子であり、前記沈降粒子が、磁性粒子である、請求項3に記載の広域スペクトルキナーゼ結合剤。
- 前記機能的要素が、検出可能な要素、親和性要素、及び捕捉要素から選択される、請求項2に記載の広域スペクトルキナーゼ結合剤。
- 前記機能的要素が検出可能な要素であり、前記検出可能な要素が、フルオロフォア、発色団、放射性核種、電子不透過性分子、MRI造影剤、SPECT造影剤、または質量タグを含む、請求項5に記載の広域スペクトルキナーゼ結合剤。
- 前記CC-1852が機能的要素に直接結合している、請求項2、5及び6のいずれか1項に記載の広域スペクトルキナーゼ結合剤。
- 前記CC-1852がリンカーを介して機能的要素に結合されている、請求項2、5及び6のいずれか1項に記載の広域スペクトルキナーゼ結合剤。
- 前記リンカーが、-[(CH2)2O]n-(式中、nは1~20である)を含む、請求項8に記載の広域スペクトルキナーゼ結合剤。
- 前記リンカーと前記CC-1852を結合している結合及び/または前記リンカーと前記機能的要素を結合している結合が、アミド結合である、請求項9に記載の広域スペクトルキナーゼ結合剤。
- 下記構造:
(式中、Xは機能的要素または固体表面である)を含む、請求項2~6及び8~10のいずれか1項に記載の広域スペクトルキナーゼ結合剤。 - Xが機能的要素であり、前記機能的要素がフルオロフォアである、請求項11に記載の広域スペクトルキナーゼ結合剤。
- 非天然存在比の1つ以上の安定した重同位体を含む、請求項2及び5~11のいずれか1項に記載の広域スペクトルキナーゼ結合剤。
- 非天然存在比の1つ以上の安定した重同位体を含む、請求項12または13に記載の広域スペクトルキナーゼ結合剤。
- 非天然存在比の1つ以上の安定した重同位体を含む、請求項3または4に記載の広域スペクトルキナーゼ結合剤。
- 非天然存在比の1つ以上の安定した重同位体を含む、請求項1に記載の広域スペクトルキナーゼ結合剤。
- 請求項1~17のいずれか1項に記載の広域スペクトルキナーゼ結合剤を含む、キナーゼを検出または定量化するための組成物。
- 試料中のキナーゼを検出または定量化する方法であって、前記試料を請求項2及び5~15のいずれか1項に記載の広域スペクトルキナーゼ結合剤と接触させる工程と、前記機能的要素またはそれによって生成されたシグナルを検出または定量化する工程と、を含む、前記方法。
- 前記機能的要素またはそれによって生成されたシグナルが、蛍光、質量分析、光学イメージング、磁気共鳴イメージング(MRI)、及びエネルギー転移によって検出または定量化される、請求項19に記載の方法。
- 試料からキナーゼを単離する方法であって、前記試料を請求項2~11、14及び16のいずれか1項に記載の広域スペクトルキナーゼ結合剤と接触させる工程と、前記広域スペクトルキナーゼ結合剤と結合したキナーゼを前記試料の非結合部分から分離する工程と、を含む、前記方法。
- 試料中のキナーゼが何であるかを特徴付ける方法であって、請求項21に記載の方法によって試料からキナーゼを単離する工程と、単離されたキナーゼを質量分析によって分析する工程と、を含む、前記方法。
- 前記試料が、細胞、細胞ライセート、体液、組織、生物学的試料、インビトロ試料、及び環境試料から選択される、請求項19~22のいずれか1項に記載の方法。
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