NZ583956A - Method and reagent for measuring nitroreductase enzyme activity - Google Patents
Method and reagent for measuring nitroreductase enzyme activityInfo
- Publication number
- NZ583956A NZ583956A NZ583956A NZ58395605A NZ583956A NZ 583956 A NZ583956 A NZ 583956A NZ 583956 A NZ583956 A NZ 583956A NZ 58395605 A NZ58395605 A NZ 58395605A NZ 583956 A NZ583956 A NZ 583956A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- dimethyl
- indolinylidenemethyl
- methyl
- dinitrobenzyl
- Prior art date
Links
- 108020001162 nitroreductase Proteins 0.000 title claims abstract description 70
- 102000004459 Nitroreductase Human genes 0.000 title claims abstract description 60
- 230000000694 effects Effects 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title description 25
- 239000003153 chemical reaction reagent Substances 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- 239000000758 substrate Substances 0.000 claims abstract description 41
- 238000005259 measurement Methods 0.000 claims abstract description 13
- 238000001514 detection method Methods 0.000 claims abstract description 9
- 239000000975 dye Substances 0.000 claims description 69
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 239000005864 Sulphur Substances 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical group O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 8
- 238000001727 in vivo Methods 0.000 claims description 7
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 229940125904 compound 1 Drugs 0.000 claims description 3
- 229940125782 compound 2 Drugs 0.000 claims description 3
- 229940126214 compound 3 Drugs 0.000 claims description 3
- 229940125898 compound 5 Drugs 0.000 claims description 3
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical group COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 3
- IMGNOSJOEJVQJM-UHFFFAOYSA-N (4e)-2-[(e)-[3,3-dimethyl-5-sulfo-1-(4-sulfobutyl)indol-2-ylidene]methyl]-4-[(1-methyl-6-nitroquinolin-1-ium-2-yl)methylidene]-3-oxocyclobuten-1-olate Chemical compound C1=CC2=CC([N+]([O-])=O)=CC=C2[N+](C)=C1C=C1C(=O)C(C=C2C(C3=CC(=CC=C3N2CCCCS(O)(=O)=O)S(O)(=O)=O)(C)C)=C1[O-] IMGNOSJOEJVQJM-UHFFFAOYSA-N 0.000 claims description 2
- AYCQUKLJEBZXAM-UHFFFAOYSA-N 2-[[1-(5-carboxypentyl)-3,3-dimethylindol-2-ylidene]methyl]-4-[[1-[(3,5-dinitrophenyl)methyl]-3,3-dimethylindol-1-ium-2-yl]methylidene]-3-oxocyclobuten-1-olate Chemical compound OC(=O)CCCCCN1C2=CC=CC=C2C(C)(C)\C1=C\C(C/1=O)=C([O-])\C\1=C/C(C(C1=CC=CC=C11)(C)C)=[N+]1CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 AYCQUKLJEBZXAM-UHFFFAOYSA-N 0.000 claims description 2
- OGSZZOPVPJEWBA-UHFFFAOYSA-N (4Z)-2-[(E)-[1-(5-carboxypentyl)-5-methoxy-3,3-dimethylindol-2-ylidene]methyl]-4-[[1-[(3,5-dinitrophenyl)methyl]-5-methoxy-3,3-dimethylindol-1-ium-2-yl]methylidene]-3-oxocyclobuten-1-olate Chemical compound CC1(C)C2=CC(OC)=CC=C2N(CCCCCC(O)=O)C1=CC(C1=O)=C([O-])C1=CC(C(C1=CC(OC)=CC=C11)(C)C)=[N+]1CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 OGSZZOPVPJEWBA-UHFFFAOYSA-N 0.000 claims 2
- INJBXCHXYYOKAF-UHFFFAOYSA-N (4Z)-4-[[1-(5-carboxypentyl)-3,3-dimethylbenzo[g]indol-1-ium-2-yl]methylidene]-2-[(E)-[1-[(3,5-dinitrophenyl)methyl]-3,3-dimethylindol-2-ylidene]methyl]-3-oxocyclobuten-1-olate Chemical compound C12=CC=CC=C2C(C)(C)\C(=C/C=2C(\C(=C/C=3C(C4=C(C5=CC=CC=C5C=C4)[N+]=3CCCCCC(O)=O)(C)C)\C=2[O-])=O)N1CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 INJBXCHXYYOKAF-UHFFFAOYSA-N 0.000 claims 1
- SLUJLSLVYSKSBO-UHFFFAOYSA-N (4Z)-4-[[1-[(3,5-dinitrophenyl)methyl]-5-methoxy-3,3-dimethylindol-1-ium-2-yl]methylidene]-2-[(E)-(1-ethyl-5-methoxy-3,3-dimethylindol-2-ylidene)methyl]-3-oxocyclobuten-1-olate Chemical compound CC1(C)C2=CC(OC)=CC=C2N(CC)C1=CC(C1=O)=C([O-])C1=CC(C(C1=CC(OC)=CC=C11)(C)C)=[N+]1CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 SLUJLSLVYSKSBO-UHFFFAOYSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- ZXXHMBXKWQQRCJ-UHFFFAOYSA-N 2-[[1-[(3,5-dinitrophenyl)methyl]-3,3-dimethylindol-2-ylidene]methyl]-3-oxo-4-[(1,3,3-trimethylindol-1-ium-2-yl)methylidene]cyclobuten-1-olate Chemical compound CC1(C)C2=CC=CC=C2[N+](C)=C1\C=C(C1=O)/C([O-])=C1/C=C(C(C1=CC=CC=C11)(C)C)\N1CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 ZXXHMBXKWQQRCJ-UHFFFAOYSA-N 0.000 claims 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 12
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Classifications
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- 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
- C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/007—Squaraine dyes
-
- 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
- C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
- C12Q1/32—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving dehydrogenase
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2500/00—Screening for compounds of potential therapeutic value
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Molecular Biology (AREA)
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- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0411993.9A GB0411993D0 (en) | 2004-05-28 | 2004-05-28 | Method and reagent for measuring nitroreductase enzyme activity |
| NZ551506A NZ551506A (en) | 2004-05-28 | 2005-05-24 | Method and reagent for measuring nitroreductase enzyme activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ583956A true NZ583956A (en) | 2011-08-26 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ583956A NZ583956A (en) | 2004-05-28 | 2005-05-24 | Method and reagent for measuring nitroreductase enzyme activity |
| NZ551506A NZ551506A (en) | 2004-05-28 | 2005-05-24 | Method and reagent for measuring nitroreductase enzyme activity |
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| NZ551506A NZ551506A (en) | 2004-05-28 | 2005-05-24 | Method and reagent for measuring nitroreductase enzyme activity |
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| EP (1) | EP1749103B1 (cg-RX-API-DMAC7.html) |
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| CN (1) | CN1993477A (cg-RX-API-DMAC7.html) |
| AT (1) | ATE553215T1 (cg-RX-API-DMAC7.html) |
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| CA (2) | CA2778894C (cg-RX-API-DMAC7.html) |
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| NZ (2) | NZ583956A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2005118839A1 (cg-RX-API-DMAC7.html) |
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| JP5214967B2 (ja) | 2004-08-13 | 2013-06-19 | エポック バイオサイエンシズ インコーポレーティッド | ホスホン酸蛍光色素および複合体 |
| US7767834B2 (en) * | 2004-08-13 | 2010-08-03 | Elitech Holding B.V. | Phosphonylated fluorescent dyes and conjugates |
| GB0505777D0 (en) * | 2005-03-22 | 2005-04-27 | Amersham Biosciences Uk Ltd | Enzyme detection method and reagent |
| GB0800938D0 (en) | 2008-01-18 | 2008-02-27 | Ge Healthcare Uk Ltd | Multiplex cell signalling assay |
| WO2010151592A1 (en) * | 2009-06-23 | 2010-12-29 | Bayer Healthcare Llc | System and apparatus for determining temperatures in a fluid analyte system |
| JP5535664B2 (ja) * | 2010-01-15 | 2014-07-02 | 株式会社Ａｄｅｋａ | 色調補正剤、スクアリリウム化合物及び光学フィルター |
| US8828678B2 (en) | 2010-11-16 | 2014-09-09 | Enzo Life Sciences, Inc. | Self-immolative probes for enzyme activity detection |
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| US5039818A (en) * | 1986-02-27 | 1991-08-13 | Syntex (U.S.A.) Inc. | Squaraine dye |
| US5403686A (en) * | 1993-09-27 | 1995-04-04 | Eastman Kodak Company | Electrophotographic element and imaging method exhibiting reduced incidence of laser interference patterns |
| JP2000508709A (ja) * | 1996-04-19 | 2000-07-11 | アマーシャム・ファルマシア・バイオテック・ユーケイ・リミテッド | スクアラート染料類および蛍光配列決定法におけるそれらの使用 |
| US6403807B1 (en) | 1999-07-06 | 2002-06-11 | Surromed, Inc. | Bridged fluorescent dyes, their preparation and their use in assays |
| GB0002261D0 (en) * | 2000-02-02 | 2000-03-22 | Amersham Pharm Biotech Uk Ltd | Fluorescent detection method & reagent |
| AU2003224912A1 (en) * | 2002-04-10 | 2003-10-27 | Igor Borovoy | Dyes and fluorescent compounds |
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2004
- 2004-05-28 GB GBGB0411993.9A patent/GB0411993D0/en not_active Ceased
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- 2005-05-24 CN CNA200580025476XA patent/CN1993477A/zh active Pending
- 2005-05-24 US US11/569,682 patent/US7579140B2/en not_active Expired - Fee Related
- 2005-05-24 WO PCT/GB2005/002057 patent/WO2005118839A1/en not_active Ceased
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- 2005-05-24 AT AT05746539T patent/ATE553215T1/de active
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- 2005-05-24 AU AU2005250209A patent/AU2005250209B2/en not_active Ceased
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2008500828A (ja) | 2008-01-17 |
| US8378120B2 (en) | 2013-02-19 |
| CA2568754C (en) | 2012-08-21 |
| EP1749103A1 (en) | 2007-02-07 |
| NZ551506A (en) | 2010-04-30 |
| CA2778894C (en) | 2013-12-31 |
| EP1749103B1 (en) | 2012-04-11 |
| AU2005250209A1 (en) | 2005-12-15 |
| GB0411993D0 (en) | 2004-06-30 |
| AU2005250209B2 (en) | 2009-07-30 |
| US20090325209A1 (en) | 2009-12-31 |
| WO2005118839A1 (en) | 2005-12-15 |
| JP4838239B2 (ja) | 2011-12-14 |
| CA2568754A1 (en) | 2005-12-15 |
| ATE553215T1 (de) | 2012-04-15 |
| US7579140B2 (en) | 2009-08-25 |
| US20080317674A1 (en) | 2008-12-25 |
| CA2778894A1 (en) | 2005-12-15 |
| CN1993477A (zh) | 2007-07-04 |
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