CN101440089A - 涉及发光化合物的组合物、方法和试剂盒 - Google Patents
涉及发光化合物的组合物、方法和试剂盒 Download PDFInfo
- Publication number
- CN101440089A CN101440089A CNA2008101694033A CN200810169403A CN101440089A CN 101440089 A CN101440089 A CN 101440089A CN A2008101694033 A CNA2008101694033 A CN A2008101694033A CN 200810169403 A CN200810169403 A CN 200810169403A CN 101440089 A CN101440089 A CN 101440089A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- compound
- twinkler
- enzyme
- aryl
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 title claims abstract description 58
- 150000001875 compounds Chemical class 0.000 title claims description 113
- 108060001084 Luciferase Proteins 0.000 claims abstract description 36
- 239000005089 Luciferase Substances 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 112
- 102000010637 Aquaporins Human genes 0.000 claims description 111
- 108010063290 Aquaporins Proteins 0.000 claims description 111
- 241000242583 Scyphozoa Species 0.000 claims description 102
- 108090000790 Enzymes Proteins 0.000 claims description 86
- 102000004190 Enzymes Human genes 0.000 claims description 86
- 125000003118 aryl group Chemical group 0.000 claims description 47
- -1 butyryl radicals Chemical class 0.000 claims description 46
- 108010047357 Luminescent Proteins Proteins 0.000 claims description 44
- 102000006830 Luminescent Proteins Human genes 0.000 claims description 44
- 239000000243 solution Substances 0.000 claims description 41
- 238000010511 deprotection reaction Methods 0.000 claims description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 28
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 238000001514 detection method Methods 0.000 claims description 20
- 108010052090 Renilla Luciferases Proteins 0.000 claims description 18
- 210000002966 serum Anatomy 0.000 claims description 18
- 238000012360 testing method Methods 0.000 claims description 18
- 244000309466 calf Species 0.000 claims description 17
- 230000002829 reductive effect Effects 0.000 claims description 17
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- 125000002587 enol group Chemical group 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 108090000371 Esterases Proteins 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims 9
- 239000013592 cell lysate Substances 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 abstract description 15
- 102000004169 proteins and genes Human genes 0.000 abstract description 11
- YHIPILPTUVMWQT-UHFFFAOYSA-N Oplophorus luciferin Chemical class C1=CC(O)=CC=C1CC(C(N1C=C(N2)C=3C=CC(O)=CC=3)=O)=NC1=C2CC1=CC=CC=C1 YHIPILPTUVMWQT-UHFFFAOYSA-N 0.000 abstract description 3
- 230000002255 enzymatic effect Effects 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 59
- 238000004458 analytical method Methods 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 41
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 230000000903 blocking effect Effects 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000000523 sample Substances 0.000 description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- 239000011159 matrix material Substances 0.000 description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 13
- 239000003153 chemical reaction reagent Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- 230000003993 interaction Effects 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 238000004020 luminiscence type Methods 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- 230000009466 transformation Effects 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 238000001890 transfection Methods 0.000 description 9
- 239000002002 slurry Substances 0.000 description 8
- 150000002085 enols Chemical class 0.000 description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000012491 analyte Substances 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XOFKYIUILQCCQE-UHFFFAOYSA-N (3-oxo-1-phenylprop-1-en-2-yl) acetate Chemical compound C(C)(=O)OC(C=O)=CC1=CC=CC=C1 XOFKYIUILQCCQE-UHFFFAOYSA-N 0.000 description 5
- 241000254173 Coleoptera Species 0.000 description 5
- 238000001212 derivatisation Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 210000001672 ovary Anatomy 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 230000036962 time dependent Effects 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 101100230376 Acetivibrio thermocellus (strain ATCC 27405 / DSM 1237 / JCM 9322 / NBRC 103400 / NCIMB 10682 / NRRL B-4536 / VPI 7372) celI gene Proteins 0.000 description 4
- 108010000239 Aequorin Proteins 0.000 description 4
- 241000699802 Cricetulus griseus Species 0.000 description 4
- 241001443978 Oplophorus Species 0.000 description 4
- 108700008625 Reporter Genes Proteins 0.000 description 4
- 238000000225 bioluminescence resonance energy transfer Methods 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HNGMHWCZZWCBON-UHFFFAOYSA-N 3-benzyl-5-phenylpyrazin-2-amine Chemical class NC1=NC=C(C=2C=CC=CC=2)N=C1CC1=CC=CC=C1 HNGMHWCZZWCBON-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 206010002368 Anger Diseases 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- 239000004098 Tetracycline Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QGJOFJXBPKBTHA-UHFFFAOYSA-N [O].O=C1N=CC=N1 Chemical compound [O].O=C1N=CC=N1 QGJOFJXBPKBTHA-UHFFFAOYSA-N 0.000 description 3
- NHYXMAKLBXBVEO-UHFFFAOYSA-N bromomethyl acetate Chemical compound CC(=O)OCBr NHYXMAKLBXBVEO-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 239000013612 plasmid Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 3
- 229960002180 tetracycline Drugs 0.000 description 3
- 229930101283 tetracycline Natural products 0.000 description 3
- 235000019364 tetracycline Nutrition 0.000 description 3
- 150000003522 tetracyclines Chemical class 0.000 description 3
- 238000009834 vaporization Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZKAMEFMDQNTDFK-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyrazine Chemical compound C1=CN=C2NC=NC2=N1 ZKAMEFMDQNTDFK-UHFFFAOYSA-N 0.000 description 2
- 239000001903 2-oxo-3-phenylpropanoic acid Substances 0.000 description 2
- BWNPYAKFDUFNND-UHFFFAOYSA-N 4-(5-amino-6-benzylpyrazin-2-yl)phenol Chemical compound NC1=NC=C(C=2C=CC(O)=CC=2)N=C1CC1=CC=CC=C1 BWNPYAKFDUFNND-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- 241000963438 Gaussia <copepod> Species 0.000 description 2
- 229910010199 LiAl Inorganic materials 0.000 description 2
- 229930193140 Neomycin Natural products 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 102000035195 Peptidases Human genes 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 241000242739 Renilla Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- DEDGUGJNLNLJSR-UHFFFAOYSA-N alpha-hydroxycinnamic acid Natural products OC(=O)C(O)=CC1=CC=CC=C1 DEDGUGJNLNLJSR-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 210000004748 cultured cell Anatomy 0.000 description 2
- 108010031180 cypridina luciferase Proteins 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 2
- 230000002068 genetic effect Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 229960004927 neomycin Drugs 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- CJIIERPDFZUYPI-UHFFFAOYSA-N oxidized Oplophorus luciferin Chemical compound C1=CC(O)=CC=C1CC(=O)NC1=NC=C(C=2C=CC(O)=CC=2)N=C1CC1=CC=CC=C1 CJIIERPDFZUYPI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000011535 reaction buffer Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- BZGWZLIKWOCPLN-UHFFFAOYSA-N 1,3-benzothiazole;quinoline Chemical compound C1=CC=C2SC=NC2=C1.N1=CC=CC2=CC=CC=C21 BZGWZLIKWOCPLN-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 1
- RLFZYIUUQBHRNV-UHFFFAOYSA-N 2,5-dihydrooxadiazole Chemical compound C1ONN=C1 RLFZYIUUQBHRNV-UHFFFAOYSA-N 0.000 description 1
- MSFXPXIVPZXOKN-UHFFFAOYSA-N 2-acetyloxy-3-phenylprop-2-enoic acid Chemical compound CC(=O)OC(C(O)=O)=CC1=CC=CC=C1 MSFXPXIVPZXOKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-QYKNYGDISA-N 2-deuteriophenol Chemical compound [2H]C1=CC=CC=C1O ISWSIDIOOBJBQZ-QYKNYGDISA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- 108010013043 Acetylesterase Proteins 0.000 description 1
- 108020004774 Alkaline Phosphatase Proteins 0.000 description 1
- 102000002260 Alkaline Phosphatase Human genes 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 102000003916 Arrestin Human genes 0.000 description 1
- 108090000328 Arrestin Proteins 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- QXFQWZCMFKOWJJ-UHFFFAOYSA-N CC(OBrC)=O Chemical compound CC(OBrC)=O QXFQWZCMFKOWJJ-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 241000035538 Cypridina Species 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 244000182625 Dictamnus albus Species 0.000 description 1
- 101000925662 Enterobacteria phage PRD1 Endolysin Proteins 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- IUWPPNJCPPZUSD-UHFFFAOYSA-N N1CCOCC1.O1C=NC=C1 Chemical compound N1CCOCC1.O1C=NC=C1 IUWPPNJCPPZUSD-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102000003992 Peroxidases Human genes 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
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 101100084449 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PRP4 gene Proteins 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 241000238584 Vargula Species 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- WQZGKKKJIJFFOK-PQMKYFCFSA-N alpha-D-mannose Chemical compound OC[C@H]1O[C@H](O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-PQMKYFCFSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N beta-D-fructofuranoseose Natural products OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- WQZGKKKJIJFFOK-FPRJBGLDSA-N beta-D-galactose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-FPRJBGLDSA-N 0.000 description 1
- 238000011953 bioanalysis Methods 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 238000005415 bioluminescence Methods 0.000 description 1
- 230000029918 bioluminescence Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000006143 cell culture medium Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 1
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000009585 enzyme analysis Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 238000012886 linear function Methods 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 description 1
- HOVAGTYPODGVJG-UHFFFAOYSA-N methyl beta-galactoside Natural products COC1OC(CO)C(O)C(O)C1O HOVAGTYPODGVJG-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000012846 protein folding Effects 0.000 description 1
- 229940121649 protein inhibitor Drugs 0.000 description 1
- 239000012268 protein inhibitor Substances 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000008259 solid foam Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003153 stable transfection Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 150000008496 α-D-glucosides Chemical class 0.000 description 1
- 150000008498 β-D-glucosides Chemical class 0.000 description 1
Images
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
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/533—Production of labelled immunochemicals with fluorescent label
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- C12Q1/66—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving luciferase
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Microbiology (AREA)
- Hematology (AREA)
- Zoology (AREA)
- Urology & Nephrology (AREA)
- Biotechnology (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- General Physics & Mathematics (AREA)
- Biophysics (AREA)
- Medicinal Chemistry (AREA)
- Food Science & Technology (AREA)
- Cell Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Pathology (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Luminescent Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Farming Of Fish And Shellfish (AREA)
- Decoration By Transfer Pictures (AREA)
- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/053,482 US7268229B2 (en) | 2001-11-02 | 2001-11-02 | Compounds to co-localize luminophores with luminescent proteins |
| US10/053482 | 2001-11-02 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB028266773A Division CN100439338C (zh) | 2001-11-02 | 2002-11-01 | 涉及发光化合物的组合物、方法和试剂盒 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101440089A true CN101440089A (zh) | 2009-05-27 |
Family
ID=21984572
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2008101694033A Pending CN101440089A (zh) | 2001-11-02 | 2002-11-01 | 涉及发光化合物的组合物、方法和试剂盒 |
| CNB028266773A Expired - Fee Related CN100439338C (zh) | 2001-11-02 | 2002-11-01 | 涉及发光化合物的组合物、方法和试剂盒 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB028266773A Expired - Fee Related CN100439338C (zh) | 2001-11-02 | 2002-11-01 | 涉及发光化合物的组合物、方法和试剂盒 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7268229B2 (https=) |
| EP (2) | EP1894933B1 (https=) |
| JP (1) | JP4958388B2 (https=) |
| CN (2) | CN101440089A (https=) |
| AT (1) | ATE399784T1 (https=) |
| CA (1) | CA2462506C (https=) |
| DE (1) | DE60227408D1 (https=) |
| DK (1) | DK1451155T3 (https=) |
| ES (1) | ES2307829T3 (https=) |
| WO (1) | WO2003040100A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113683617A (zh) * | 2021-07-16 | 2021-11-23 | 山东大学 | 一种基于腔肠素-h的氘代化合物及其制备方法与应用 |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1546162B1 (en) | 2002-09-20 | 2011-06-22 | Promega Corporation | Luminescence-based methods and probes for measuring cytochrome p450 activity |
| JP4485470B2 (ja) | 2002-12-23 | 2010-06-23 | プロメガ コーポレイション | ルシフェラーゼ酵素活性を保護するための方法及びキット |
| EP2272972A1 (en) | 2005-05-31 | 2011-01-12 | Promega Corporation | Luminogenic and fluorogenic compounds and methods to detect molecules or conditions |
| US7709468B2 (en) | 2005-09-02 | 2010-05-04 | Abbott Laboratories | Imidazo based heterocycles |
| JP2007081050A (ja) * | 2005-09-13 | 2007-03-29 | Fujifilm Corp | 有機電界発光素子 |
| JP4982737B2 (ja) * | 2006-03-23 | 2012-07-25 | 国立大学法人三重大学 | イミダゾキノキザリノン化学発光物質、その製造法、および発光分析法 |
| JP2007277097A (ja) * | 2006-04-03 | 2007-10-25 | Mie Univ | 発光化合物、発光方法、及びその製造方法 |
| US7709253B2 (en) * | 2006-08-04 | 2010-05-04 | The Board Of Trustees Of The Leland Stanford Junior University | Ligand-regulable transactivation systems, methods of use thereof, methods of detecting estrogen receptor ligands, and methods of differentiating estrogen receptor ligand agonists and antagonists |
| JP5844029B2 (ja) * | 2006-10-24 | 2016-01-13 | ジーン ストリーム ピーティーワイ エルティーディ | ルシフェラーゼシグナルを増強する組成物 |
| US20090075309A1 (en) * | 2007-09-06 | 2009-03-19 | Gambhir Sanjiv S | Bisdeoxycoelenterazine derivatives, methods of use, and BRET2 systems |
| EP2326953B1 (en) | 2008-07-22 | 2018-03-21 | Promega Corporation | Adp detection based luminescent phosphotransferase or atp hydrolase assay |
| US8288559B2 (en) | 2008-08-18 | 2012-10-16 | Promega Corporation | Luminogenic compounds and methods to detect cytochrome P450 3A enzymes |
| WO2010090319A1 (ja) | 2009-02-09 | 2010-08-12 | チッソ株式会社 | セレンテラジン類縁体及びその製造方法 |
| ES2795287T3 (es) | 2009-05-01 | 2020-11-23 | Promega Corp | Luciferasas de Oplophorus sintéticas con mayor emisión de luz |
| JP5605727B2 (ja) * | 2010-04-06 | 2014-10-15 | Jnc株式会社 | セレンテラジン類縁体及びセレンテラミド類縁体 |
| SG185481A1 (en) | 2010-05-10 | 2012-12-28 | Univ California | Endoribonuclease compositions and methods of use thereof |
| CN103180324A (zh) * | 2010-11-02 | 2013-06-26 | 普罗美加公司 | 腔肠素衍生物及其使用方法 |
| SG10202103336SA (en) | 2010-11-02 | 2021-04-29 | Promega Corp | Novel coelenterazine substrates and methods of use |
| JP6067019B2 (ja) * | 2011-09-02 | 2017-01-25 | プロメガ コーポレイションPromega Corporation | 代謝的に活性な細胞の酸化還元状態を評価するための化合物及び方法、ならびにnad(p)/nad(p)hを測定するための方法 |
| JP6511720B2 (ja) | 2013-02-28 | 2019-05-15 | Jnc株式会社 | コドン最適化変異エビルシフェラーゼ遺伝子およびその使用方法 |
| JP6040846B2 (ja) | 2013-04-08 | 2016-12-07 | Jnc株式会社 | セレンテラジン類縁体 |
| JP6484987B2 (ja) | 2013-10-21 | 2019-03-20 | Jnc株式会社 | エビルシフェラーゼの触媒蛋白質の変異遺伝子とその使用法 |
| JP6442825B2 (ja) | 2013-12-26 | 2018-12-26 | Jnc株式会社 | エビルシフェラーゼの触媒蛋白質の変異遺伝子とその使用法 |
| US9790537B2 (en) | 2014-01-29 | 2017-10-17 | Promega Corporation | Quinone-masked probes as labeling reagents for cell uptake measurements |
| EP3099691B1 (en) | 2014-01-29 | 2019-11-20 | Promega Corporation | Pro-substrates for live cell applications |
| JP6265020B2 (ja) | 2014-04-16 | 2018-01-24 | Jnc株式会社 | エビルシフェラーゼの触媒蛋白質の変異遺伝子とその使用法 |
| US9732373B2 (en) * | 2014-09-11 | 2017-08-15 | Promega Corporation | Luciferase sequences utilizing infrared-emitting substrates to produce enhanced luminescence |
| JP6814132B2 (ja) | 2014-09-12 | 2021-01-13 | プロメガ コーポレイションPromega Corporation | 内部タンパク質タグ |
| US9677117B2 (en) | 2014-10-08 | 2017-06-13 | Promega Corporation | Bioluminescent succinate detection assay |
| WO2016210294A1 (en) | 2015-06-25 | 2016-12-29 | Promega Corporation | Thienopyrrole compounds and uses thereof as inhibitors of oplophorus-derived luciferases |
| JP7092677B2 (ja) | 2016-02-15 | 2022-06-28 | プロメガ コーポレイション | セレンテラジン類似体 |
| WO2018049241A1 (en) | 2016-09-09 | 2018-03-15 | Promega Corporation | Dual protected pro-coelenterazine substrates |
| JP7200102B2 (ja) | 2016-11-01 | 2023-01-06 | プロメガ コーポレイション | エネルギー受容体に係留されたセレンテラジン類縁体 |
| EP3548492B1 (en) | 2016-12-01 | 2023-07-05 | Promega Corporation | Cell impermeable coelenterazine analogues |
| WO2018125992A1 (en) | 2016-12-28 | 2018-07-05 | Promega Corporation | Functionalized nanoluc inhibitors |
| EP3395803A1 (en) | 2017-04-28 | 2018-10-31 | Institut Pasteur | Imidazopyrazine derivatives, process for preparation thereof, and their uses as luciferins |
| ES2983923T3 (es) * | 2017-07-06 | 2024-10-28 | Promega Corp | Análogos de la pro-coelenterazina estables en suero |
| JP7419260B2 (ja) | 2018-05-01 | 2024-01-22 | プロメガ コーポレイション | NanoLuc自殺基質としてのセレンテラジン化合物 |
| EP3802514B1 (en) | 2018-06-01 | 2022-08-03 | Promega Corporation | Inhibitors of oplophorus luciferase-derived bioluminescent complexes |
| WO2020023871A1 (en) | 2018-07-27 | 2020-01-30 | Promega Corporation | Quinone-containing conjugates |
| CA3114424A1 (en) | 2018-10-03 | 2020-04-09 | Promega Corporation | Compositions and methods for stabilizing coelenterazine and analogs and derivatives thereof |
| EP4600650A3 (en) | 2019-04-05 | 2025-11-26 | Earli Inc. | Improved methods and compositions for synthetic biomarkers |
| US12582726B1 (en) | 2019-04-05 | 2026-03-24 | Earli Inc. | Synthetic cancer-specific promoters |
| CA3158729A1 (en) | 2019-11-27 | 2021-06-03 | Virginia Kincaid | Multipartite luciferase peptides and polypeptides |
| JP7745550B2 (ja) | 2019-12-10 | 2025-09-29 | プロメガ コーポレイション | 多官能性プローブを使用する生物発光検出用組成物及び生物発光検出方法 |
| US20210363565A1 (en) | 2020-05-22 | 2021-11-25 | Promega Corporation | Enhancement of kinase target engagement |
| US12606863B2 (en) | 2021-05-13 | 2026-04-21 | Promega Corporation | Bioluminescent detection of DNA synthesis |
| WO2023215505A1 (en) | 2022-05-04 | 2023-11-09 | Promega Corporation | Modified dehalogenase with extended surface loop regions |
| EP4519385A2 (en) | 2022-05-04 | 2025-03-12 | Promega Corporation | Bioluminescence-triggered photocatalytic labeling |
Family Cites Families (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4604364A (en) | 1974-01-04 | 1986-08-05 | Kosak Kenneth M | Bioluminescent tracer composition and method of use in immunoassays |
| US4080265A (en) | 1974-08-02 | 1978-03-21 | Antonik Alan S | Method for the determination of creative phosphokinase enzyme |
| US3958938A (en) | 1974-12-16 | 1976-05-25 | Bausch & Lomb Incorporated | Bioluminescent sensor system |
| US4349510A (en) | 1979-07-24 | 1982-09-14 | Seppo Kolehmainen | Method and apparatus for measurement of samples by luminescence |
| SE449004B (sv) | 1981-06-25 | 1987-03-30 | Wallac Oy | Bioluminiscensbestemning av nadh och/eller nadph |
| IT1172385B (it) | 1983-12-21 | 1987-06-18 | Miles Italiana | Composizione e metodo per la determinazione enzimatica di atp ed fmn |
| US4665022A (en) | 1984-02-17 | 1987-05-12 | The Regents Of The University Of California | Bioluminescent assay reagent and method |
| DE3537877A1 (de) | 1985-10-24 | 1987-04-30 | Geiger Reinhard | Luciferin-derivate und immunoassays unter einsatz derartiger luciferin-derivate |
| US5004565A (en) | 1986-07-17 | 1991-04-02 | The Board Of Governors Of Wayne State University | Method and compositions providing enhanced chemiluminescence from 1,2-dioxetanes |
| DE3700908A1 (de) | 1987-01-14 | 1988-07-28 | Geiger Reinhard | Aminoluciferine, verfahren zu deren herstellung und deren verwendung bei der bestimmung von enzymaktivitaeten |
| JPS6447379A (en) | 1987-08-19 | 1989-02-21 | Chisso Corp | Preparation of calcium-dependent oxygenation enzyme |
| JPH04228097A (ja) | 1990-07-02 | 1992-08-18 | Toyo Ink Mfg Co Ltd | ミルク試料からの細胞分離および濃縮方法とそのキット |
| US5283180A (en) | 1990-07-19 | 1994-02-01 | Charm Sciences, Inc. | Bioluminescence method for the determination of pesticides |
| US5374534A (en) | 1990-07-19 | 1994-12-20 | Charm Sciences, Inc. | Method of preparing D-luciferin derivatives |
| US5831102A (en) | 1990-08-30 | 1998-11-03 | Tropix, Inc. | Chemiluminescent 3-(substituted adamant-2'-ylidene) 1,2-dioxetanes |
| US5283179A (en) | 1990-09-10 | 1994-02-01 | Promega Corporation | Luciferase assay method |
| DE69219963T2 (de) | 1991-02-13 | 1997-10-16 | Hamamatsu Photonics K.K., Hamamatsu, Shizuoka | Verfahren zur bestimmung der zahl lebender mikroorganismen |
| US5784162A (en) | 1993-08-18 | 1998-07-21 | Applied Spectral Imaging Ltd. | Spectral bio-imaging methods for biological research, medical diagnostics and therapy |
| JP2856339B2 (ja) | 1991-02-21 | 1999-02-10 | キッコーマン株式会社 | 酵素免疫測定法 |
| JPH08441B2 (ja) | 1992-03-06 | 1996-01-10 | 司 上月 | 容器素材の製造方法 |
| JP3311752B2 (ja) | 1992-07-02 | 2002-08-05 | ソイニ,エルッキ | 生体特異的多変数検定法 |
| US5360728A (en) | 1992-12-01 | 1994-11-01 | Woods Hole Oceanographic Institution (W.H.O.I.) | Modified apoaequorin having increased bioluminescent activity |
| US5648232A (en) | 1993-01-21 | 1997-07-15 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Microbiological best method and reagents |
| GB9311241D0 (en) | 1993-06-01 | 1993-07-21 | Celsis Ltd | Reagents for use in bioluminescence |
| DE69433967D1 (de) | 1993-10-06 | 2004-09-30 | Univ Florida | Stammzellen-proliferations-faktor |
| JPH07125617A (ja) | 1993-11-02 | 1995-05-16 | Hino Motors Ltd | 坂道発進補助装置 |
| WO1995021191A1 (en) | 1994-02-04 | 1995-08-10 | William Ward | Bioluminescent indicator based upon the expression of a gene for a modified green-fluorescent protein |
| JP3648763B2 (ja) * | 1994-08-23 | 2005-05-18 | 日本油脂株式会社 | ウミホタルルシフェリン誘導体および糖加水分解酵素の定量方法 |
| US5840572A (en) | 1994-10-11 | 1998-11-24 | United States Of America As Represented By The Secretary Of The Navy | Bioluminescent bioassay system |
| JPH08294397A (ja) * | 1995-04-27 | 1996-11-12 | Nippon Oil & Fats Co Ltd | 免疫学的活性物質の測定方法 |
| AU713409B2 (en) | 1995-07-12 | 1999-12-02 | Charm Sciences, Inc. | Test apparatus, system and method for the detection of test samples |
| US6165734A (en) | 1995-12-12 | 2000-12-26 | Applied Spectral Imaging Ltd. | In-situ method of analyzing cells |
| JP3547882B2 (ja) | 1995-12-28 | 2004-07-28 | キッコーマン株式会社 | Atp消去剤、atp消去法、それを用いた生物細胞測定試薬及び生物細胞測定法 |
| JP3409962B2 (ja) | 1996-03-04 | 2003-05-26 | キッコーマン株式会社 | 生物発光試薬及びその試薬を用いたアデノシンリン酸エステルの定量法並びにその試薬を用いたatp変換反応系に関与する物質の定量法 |
| US5908751A (en) | 1996-04-26 | 1999-06-01 | Toyo Ink Mfg. Co., Ltd. | Method for detecting and/or determining ATP from microorganism cells in a sample |
| US6416960B1 (en) * | 1996-08-08 | 2002-07-09 | Prolume, Ltd. | Detection and visualization of neoplastic tissues and other tissues |
| US5798263A (en) | 1996-09-05 | 1998-08-25 | Promega Corporation | Apparatus for quantifying dual-luminescent reporter assays |
| GB9626932D0 (en) | 1996-12-24 | 1997-02-12 | Lumitech Limited | Assay methods and kits therefor |
| US6171809B1 (en) | 1998-01-29 | 2001-01-09 | Packard Instrument Company | Method and compositions for detecting luciferase biological samples |
| CA2324648C (en) * | 1998-03-27 | 2013-02-26 | Prolume, Ltd. | Luciferases, fluorescent proteins, nucleic acids encoding the luciferases and fluorescent proteins and the use thereof in diagnostics, high throughput screening and novelty items |
| DE69928255T2 (de) | 1998-06-16 | 2006-11-09 | PerkinElmer BioSignal Inc., Montréal | Biolumineszentes resonanz-energie-transfersystem (bret) und seine anwendung |
| US6214552B1 (en) * | 1998-09-17 | 2001-04-10 | Igen International, Inc. | Assays for measuring nucleic acid damaging activities |
| US20040034225A1 (en) * | 2000-05-17 | 2004-02-19 | Jacqueline Marchand-Brynaert | Aryl-substituted n, n-heterocyclic compounds, method for their preparationand their use in therapeutics and diagnostics |
-
2001
- 2001-11-02 US US10/053,482 patent/US7268229B2/en not_active Expired - Lifetime
-
2002
- 2002-11-01 CA CA2462506A patent/CA2462506C/en not_active Expired - Fee Related
- 2002-11-01 WO PCT/US2002/034972 patent/WO2003040100A1/en not_active Ceased
- 2002-11-01 CN CNA2008101694033A patent/CN101440089A/zh active Pending
- 2002-11-01 AT AT02802815T patent/ATE399784T1/de not_active IP Right Cessation
- 2002-11-01 DK DK02802815T patent/DK1451155T3/da active
- 2002-11-01 ES ES02802815T patent/ES2307829T3/es not_active Expired - Lifetime
- 2002-11-01 CN CNB028266773A patent/CN100439338C/zh not_active Expired - Fee Related
- 2002-11-01 DE DE60227408T patent/DE60227408D1/de not_active Expired - Lifetime
- 2002-11-01 EP EP07025040.2A patent/EP1894933B1/en not_active Expired - Lifetime
- 2002-11-01 JP JP2003542146A patent/JP4958388B2/ja not_active Expired - Lifetime
- 2002-11-01 EP EP02802815A patent/EP1451155B1/en not_active Expired - Lifetime
-
2007
- 2007-08-01 US US11/832,169 patent/US7537912B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113683617A (zh) * | 2021-07-16 | 2021-11-23 | 山东大学 | 一种基于腔肠素-h的氘代化合物及其制备方法与应用 |
| CN113683617B (zh) * | 2021-07-16 | 2022-08-30 | 山东大学 | 一种基于腔肠素-h的氘代化合物及其制备方法与应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2307829T3 (es) | 2008-12-01 |
| JP4958388B2 (ja) | 2012-06-20 |
| CA2462506A1 (en) | 2003-05-15 |
| EP1451155B1 (en) | 2008-07-02 |
| JP2005515977A (ja) | 2005-06-02 |
| EP1451155A1 (en) | 2004-09-01 |
| DK1451155T3 (da) | 2008-11-10 |
| EP1894933A3 (en) | 2008-03-26 |
| US7537912B2 (en) | 2009-05-26 |
| WO2003040100A1 (en) | 2003-05-15 |
| ATE399784T1 (de) | 2008-07-15 |
| EP1451155A4 (en) | 2006-03-01 |
| CA2462506C (en) | 2010-04-06 |
| DE60227408D1 (de) | 2008-08-14 |
| EP1894933B1 (en) | 2013-07-03 |
| US20080050760A1 (en) | 2008-02-28 |
| US7268229B2 (en) | 2007-09-11 |
| EP1894933A2 (en) | 2008-03-05 |
| CN100439338C (zh) | 2008-12-03 |
| CN1612860A (zh) | 2005-05-04 |
| US20030153090A1 (en) | 2003-08-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN100439338C (zh) | 涉及发光化合物的组合物、方法和试剂盒 | |
| US4774339A (en) | Chemically reactive dipyrrometheneboron difluoride dyes | |
| US5503770A (en) | Fluorescent compound suitable for use in the detection of saccharides | |
| Takakusa et al. | A novel design method of ratiometric fluorescent probes based on fluorescence resonance energy transfer switching by spectral overlap integral | |
| US5089630A (en) | Dioxetanes for use in assays | |
| WO2008118445A1 (en) | Methods to quench light from optical reactions | |
| KR19990044694A (ko) | 개선된 성능을 갖는 화학발광 1,2-디옥세탄 | |
| JP2003520017A (ja) | 多種酵素アッセイ | |
| US6162610A (en) | Xanthan-ester and acridan substrates for horseradish peroxidase | |
| JPH0853467A (ja) | ボロン酸基を有する発蛍光性化合物 | |
| AU2004210982B2 (en) | Methods and kits for dual enzymatic assays whereby light is quenched from luminescent reactions | |
| Toya et al. | Synthesis and Chemiluminescence Properties of 6-(4-Methoxyphenyl)-2-methylimidazo (1, 2-a) pyrazin-3 (7H)-one and 2-Methyl-6-(2-naphthyl) imidazo (1, 2-a) pyrazin-3 (7H)-one. | |
| CN110885326A (zh) | 高水溶性苯基乙酸酯化合物及包含该化合物的羧酸酯酶检测试剂盒 | |
| EP0348494B1 (en) | Dioxetanes for use in assays | |
| AU7359796A (en) | 1,2 chemiluminescent dioxetanes of improved performance | |
| CN109678802A (zh) | 衍生醛基嘧啶的方法、检测5-醛基胞嘧啶的方法以及醛基嘧啶衍生物的应用 | |
| EP2048140A1 (en) | Deuterated chemiluminescent 1,2-dioxetanes | |
| AU2002363424A1 (en) | Compositions, methods and kits pertaining to luminescent compounds | |
| Musicki | Chemistry of bioluminescence: jellyfish and euphausiid bioluminescent systems |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Open date: 20090527 |