CA2778894C - Compounds for measuring nitroreductase enzyme activity - Google Patents
Compounds for measuring nitroreductase enzyme activity Download PDFInfo
- Publication number
- CA2778894C CA2778894C CA2778894A CA2778894A CA2778894C CA 2778894 C CA2778894 C CA 2778894C CA 2778894 A CA2778894 A CA 2778894A CA 2778894 A CA2778894 A CA 2778894A CA 2778894 C CA2778894 C CA 2778894C
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- CA
- Canada
- Prior art keywords
- compound
- dimethyl
- methyl
- indolinylidenemethyl
- ethyl
- 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.)
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- 150000001875 compounds Chemical class 0.000 title claims description 81
- 108020001162 nitroreductase Proteins 0.000 title abstract description 65
- 102000004459 Nitroreductase Human genes 0.000 title abstract description 55
- 230000000694 effects Effects 0.000 title abstract description 26
- 239000000975 dye Substances 0.000 claims description 71
- 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 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- FGSGOGSTNYMSHB-UHFFFAOYSA-N 4-[(3-ethyl-6-nitro-1,3-benzothiazol-3-ium-2-yl)methylidene]-2-[[1-[2-(2-methoxyethoxy)ethyl]-3,3-dimethylindol-2-ylidene]methyl]-3-oxocyclobuten-1-olate Chemical compound S1C2=CC([N+]([O-])=O)=CC=C2[N+](CC)=C1\C=C/1C(=O)C(/C=C\2C(C3=CC=CC=C3N/2CCOCCOC)(C)C)=C\1[O-] FGSGOGSTNYMSHB-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000005864 Sulphur Substances 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 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 description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 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 description 3
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- 101000883840 Macrobrachium rosenbergii Crustacean hyperglycemic hormone isoform 1 Proteins 0.000 description 1
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- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
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- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
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- 229910052794 bromium Inorganic materials 0.000 description 1
- NHYXMAKLBXBVEO-UHFFFAOYSA-N bromomethyl acetate Chemical compound CC(=O)OCBr NHYXMAKLBXBVEO-UHFFFAOYSA-N 0.000 description 1
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- 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
- 229910017604 nitric acid Inorganic materials 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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Classifications
-
- 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)
- Biotechnology (AREA)
- Biophysics (AREA)
- Analytical Chemistry (AREA)
- 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0411993.9 | 2004-05-28 | ||
| GBGB0411993.9A GB0411993D0 (en) | 2004-05-28 | 2004-05-28 | Method and reagent for measuring nitroreductase enzyme activity |
| CA2568754A CA2568754C (en) | 2004-05-28 | 2005-05-24 | Method and reagent for measuring nitroreductase enzyme activity |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2568754A Division CA2568754C (en) | 2004-05-28 | 2005-05-24 | Method and reagent for measuring nitroreductase enzyme activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2778894A1 CA2778894A1 (en) | 2005-12-15 |
| CA2778894C true CA2778894C (en) | 2013-12-31 |
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|---|---|---|---|
| CA2778894A Expired - Fee Related CA2778894C (en) | 2004-05-28 | 2005-05-24 | Compounds for measuring nitroreductase enzyme activity |
| CA2568754A Expired - Fee Related CA2568754C (en) | 2004-05-28 | 2005-05-24 | Method and reagent for measuring nitroreductase enzyme activity |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2568754A Expired - Fee Related CA2568754C (en) | 2004-05-28 | 2005-05-24 | Method and reagent for measuring nitroreductase enzyme activity |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7579140B2 (https=) |
| EP (1) | EP1749103B1 (https=) |
| JP (1) | JP4838239B2 (https=) |
| CN (1) | CN1993477A (https=) |
| AT (1) | ATE553215T1 (https=) |
| AU (1) | AU2005250209B2 (https=) |
| CA (2) | CA2778894C (https=) |
| GB (1) | GB0411993D0 (https=) |
| NZ (2) | NZ551506A (https=) |
| WO (1) | WO2005118839A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7767834B2 (en) | 2004-08-13 | 2010-08-03 | Elitech Holding B.V. | Phosphonylated fluorescent dyes and conjugates |
| EP1781675B1 (en) | 2004-08-13 | 2014-03-26 | Epoch Biosciences, Inc. | Phosphonate 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 |
| EP1196398A4 (en) | 1999-07-06 | 2002-11-06 | Surromed Inc | BRIDGED FLUORESCENT DYES, THEIR PRODUCTION AND USE IN DETECTION METHODS |
| 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 |
-
2004
- 2004-05-28 GB GBGB0411993.9A patent/GB0411993D0/en not_active Ceased
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2005
- 2005-05-24 CA CA2778894A patent/CA2778894C/en not_active Expired - Fee Related
- 2005-05-24 EP EP05746539A patent/EP1749103B1/en not_active Expired - Lifetime
- 2005-05-24 CA CA2568754A patent/CA2568754C/en not_active Expired - Fee Related
- 2005-05-24 NZ NZ551506A patent/NZ551506A/en not_active IP Right Cessation
- 2005-05-24 JP JP2007514089A patent/JP4838239B2/ja not_active Expired - Fee Related
- 2005-05-24 US US11/569,682 patent/US7579140B2/en not_active Expired - Fee Related
- 2005-05-24 CN CNA200580025476XA patent/CN1993477A/zh active Pending
- 2005-05-24 AU AU2005250209A patent/AU2005250209B2/en not_active Ceased
- 2005-05-24 AT AT05746539T patent/ATE553215T1/de active
- 2005-05-24 NZ NZ583956A patent/NZ583956A/en not_active IP Right Cessation
- 2005-05-24 WO PCT/GB2005/002057 patent/WO2005118839A1/en not_active Ceased
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2009
- 2009-07-10 US US12/500,730 patent/US8378120B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1749103B1 (en) | 2012-04-11 |
| ATE553215T1 (de) | 2012-04-15 |
| US20080317674A1 (en) | 2008-12-25 |
| NZ551506A (en) | 2010-04-30 |
| CA2568754C (en) | 2012-08-21 |
| WO2005118839A1 (en) | 2005-12-15 |
| US7579140B2 (en) | 2009-08-25 |
| GB0411993D0 (en) | 2004-06-30 |
| AU2005250209B2 (en) | 2009-07-30 |
| JP2008500828A (ja) | 2008-01-17 |
| EP1749103A1 (en) | 2007-02-07 |
| US20090325209A1 (en) | 2009-12-31 |
| CA2778894A1 (en) | 2005-12-15 |
| CN1993477A (zh) | 2007-07-04 |
| US8378120B2 (en) | 2013-02-19 |
| AU2005250209A1 (en) | 2005-12-15 |
| NZ583956A (en) | 2011-08-26 |
| CA2568754A1 (en) | 2005-12-15 |
| JP4838239B2 (ja) | 2011-12-14 |
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