JPH0553478B2 - - Google Patents
Info
- Publication number
- JPH0553478B2 JPH0553478B2 JP60173084A JP17308485A JPH0553478B2 JP H0553478 B2 JPH0553478 B2 JP H0553478B2 JP 60173084 A JP60173084 A JP 60173084A JP 17308485 A JP17308485 A JP 17308485A JP H0553478 B2 JPH0553478 B2 JP H0553478B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- peroxidase
- reaction
- assay
- fused ring
- 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.)
- Expired - Lifetime
Links
- 238000003556 assay Methods 0.000 claims description 54
- 238000006243 chemical reaction Methods 0.000 claims description 53
- 102000003992 Peroxidases Human genes 0.000 claims description 49
- 108040007629 peroxidase activity proteins Proteins 0.000 claims description 42
- 238000004020 luminiscence type Methods 0.000 claims description 34
- 239000007800 oxidant agent Substances 0.000 claims description 18
- 150000004982 aromatic amines Chemical class 0.000 claims description 11
- KGLPWQKSKUVKMJ-UHFFFAOYSA-N 2,3-dihydrophthalazine-1,4-dione Chemical compound C1=CC=C2C(=O)NNC(=O)C2=C1 KGLPWQKSKUVKMJ-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 238000005259 measurement Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 description 34
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 28
- 102100022334 Dihydropyrimidine dehydrogenase [NADP(+)] Human genes 0.000 description 27
- 101710165631 Dihydropyrimidine dehydrogenase [NADP(+)] Proteins 0.000 description 27
- 101710183660 NAD-dependent dihydropyrimidine dehydrogenase subunit PreA Proteins 0.000 description 27
- 101710183648 NAD-dependent dihydropyrimidine dehydrogenase subunit PreT Proteins 0.000 description 27
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- 239000003446 ligand Substances 0.000 description 17
- HWYHZTIRURJOHG-UHFFFAOYSA-N luminol Chemical compound O=C1NNC(=O)C2=C1C(N)=CC=C2 HWYHZTIRURJOHG-UHFFFAOYSA-N 0.000 description 17
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- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 10
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- RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical compound CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 6
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- YRNWIFYIFSBPAU-UHFFFAOYSA-N 4-[4-(dimethylamino)phenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CC=C(N(C)C)C=C1 YRNWIFYIFSBPAU-UHFFFAOYSA-N 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
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- 108010067372 Pancreatic elastase Proteins 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
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- 239000006228 supernatant Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 description 3
- FIIDVVUUWRJXLF-UHFFFAOYSA-N 4-phenylmethoxyaniline Chemical compound C1=CC(N)=CC=C1OCC1=CC=CC=C1 FIIDVVUUWRJXLF-UHFFFAOYSA-N 0.000 description 3
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- 239000000975 dye Substances 0.000 description 3
- 108010046301 glucose peroxidase Proteins 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000002207 metabolite Substances 0.000 description 3
- 150000007523 nucleic acids Chemical class 0.000 description 3
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- 230000001590 oxidative effect Effects 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- YSZIOXAEADAJLX-UHFFFAOYSA-N phthalazine-1,4-dione Chemical compound C1=CC=C2C(=O)N=NC(=O)C2=C1 YSZIOXAEADAJLX-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008313 sensitization Effects 0.000 description 3
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- PHOLIFLKGONSGY-CSKARUKUSA-N (e)-(3-methyl-1,3-benzothiazol-2-ylidene)hydrazine Chemical compound C1=CC=C2S\C(=N\N)N(C)C2=C1 PHOLIFLKGONSGY-CSKARUKUSA-N 0.000 description 2
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
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- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
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- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
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- 239000003418 antiprogestin Substances 0.000 description 2
- OHDRQQURAXLVGJ-HLVWOLMTSA-N azane;(2e)-3-ethyl-2-[(e)-(3-ethyl-6-sulfo-1,3-benzothiazol-2-ylidene)hydrazinylidene]-1,3-benzothiazole-6-sulfonic acid Chemical compound [NH4+].[NH4+].S/1C2=CC(S([O-])(=O)=O)=CC=C2N(CC)C\1=N/N=C1/SC2=CC(S([O-])(=O)=O)=CC=C2N1CC OHDRQQURAXLVGJ-HLVWOLMTSA-N 0.000 description 2
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- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
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Classifications
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- 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
- G01N33/535—Production of labelled immunochemicals with enzyme label or co-enzymes, co-factors, enzyme inhibitors or enzyme substrates
-
- 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
- C12Q1/28—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving peroxidase
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/81—Packaged device or kit
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/968—High energy substrates, e.g. fluorescent, chemiluminescent, radioactive
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/975—Kit
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/80—Fluorescent dyes, e.g. rhodamine
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Biophysics (AREA)
- Pathology (AREA)
- General Physics & Mathematics (AREA)
- Food Science & Technology (AREA)
- Cell Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848420053A GB8420053D0 (en) | 1984-08-07 | 1984-08-07 | Enhanced luminescent/luminometric assay |
| GB8420053 | 1984-08-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6154453A JPS6154453A (ja) | 1986-03-18 |
| JPH0553478B2 true JPH0553478B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-08-10 |
Family
ID=10565011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60173084A Granted JPS6154453A (ja) | 1984-08-07 | 1985-08-06 | 増感した発光又は発光測定アツセイ |
Country Status (4)
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1307480C (en) * | 1985-07-10 | 1992-09-15 | Nanibhushan Dattagupta | Prolonged chemiluminescence |
| US4853327A (en) * | 1985-07-10 | 1989-08-01 | Molecular Diagnostics, Inc. | Enhanced phthalazinedione chemiluminescence |
| US4794073A (en) * | 1985-07-10 | 1988-12-27 | Molecular Diagnostics, Inc. | Detection of nucleic acid hybrids by prolonged chemiluminescence |
| AU603342B2 (en) * | 1985-10-15 | 1990-11-15 | Minnesota Mining And Manufacturing Company | Chemiluminescent methods and kit |
| DE3545398A1 (de) * | 1985-12-20 | 1987-06-25 | Boehringer Mannheim Gmbh | Verfahren zur steigerung der quanten-ausbeute bei der oxidation von luminol durch peroxide in gegenwart von peroxidase |
| US4921791A (en) * | 1986-06-26 | 1990-05-01 | Konishiroku Photo Industry Co., Ltd. | Method for measuring specific component using peroxidase enzyme reaction |
| US4828983A (en) * | 1986-07-10 | 1989-05-09 | Eastman Kodak Company | Use of phenols and anilines to increase the rate of peroxidase catalyzed oxidation of leuco dyes |
| CA1340590C (en) * | 1986-07-24 | 1999-06-08 | John C. Voyta | Chemiluminescence enhancement |
| GB8621261D0 (en) * | 1986-09-03 | 1986-10-08 | Barnard G J R | Enhanced luminescent assay |
| GB8713951D0 (en) * | 1987-06-15 | 1987-07-22 | Dewar M H | Enhanced chemiluminescent reaction |
| JPH07114709B2 (ja) * | 1987-11-13 | 1995-12-13 | 協和メデックス株式会社 | 酵素活性の定量法 |
| GB8811294D0 (en) * | 1988-05-12 | 1988-06-15 | Kabivitrum Peptide Hormones Ab | Luminescent/luminometric assays |
| US5017471A (en) * | 1988-08-26 | 1991-05-21 | Epitope, Inc. | Reagent for peroxidase detection |
| DE68911633T2 (de) * | 1988-09-30 | 1994-04-07 | Fujirebio Kk | Verfahren zur Bestimmung von Peroxidase-Aktivität unter Verwendung von Chemilumineszenz. |
| ES2086326T3 (es) * | 1989-02-14 | 1996-07-01 | Wako Pure Chem Ind Ltd | Metodo para intensificar la quimiluminiscencia. |
| ES2074571T3 (es) * | 1989-04-28 | 1995-09-16 | Toray Industries | Metodo para la deteccion de una substancia utilizando quimioluminiscencia. |
| GB2233451B (en) * | 1989-06-27 | 1993-09-15 | Tropix Inc | Chemiluminescence enhancement |
| WO1991005063A1 (en) * | 1989-10-05 | 1991-04-18 | Exoxemis, Inc. | Haloperoxidase acid optimum chemiluminescence assay system |
| JP2977895B2 (ja) * | 1989-10-17 | 1999-11-15 | ブリティッシュ・テクノロジー・グループ・リミテッド | 増幅化学ルミネセントアッセイ |
| US5108899A (en) * | 1989-10-31 | 1992-04-28 | Exoxemis, Inc. | Chemiluminescence assay of in vivo inflammation |
| JPH03262498A (ja) * | 1990-03-12 | 1991-11-22 | Nichirei Corp | 魚介類の鮮度測定方法及び測定装置 |
| IE66038B1 (en) * | 1990-06-12 | 1995-12-13 | British Tech Group | Antioxidant assay |
| IE74193B1 (en) * | 1990-08-23 | 1997-07-16 | Enfer Tech Ltd | Hormone detection methods |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4290773A (en) * | 1979-11-13 | 1981-09-22 | Miles Laboratories, Inc. | Stabilization of benzidine-type indicators with various enhancers |
| DE3463395D1 (en) * | 1983-02-11 | 1987-06-04 | Nat Res Dev | Enhanced luminescent or luminometric assay |
| US4556640A (en) * | 1983-06-29 | 1985-12-03 | Miles Laboratories, Inc. | Stabilized test composition, device and method for the determination of peroxidatively active substances |
-
1984
- 1984-08-07 GB GB848420053A patent/GB8420053D0/en active Pending
-
1985
- 1985-07-29 US US06/760,036 patent/US4729950A/en not_active Expired - Lifetime
- 1985-08-02 GB GB08519544A patent/GB2162946B/en not_active Expired
- 1985-08-06 JP JP60173084A patent/JPS6154453A/ja active Granted
- 1985-08-07 DE DE3528391A patent/DE3528391C2/de not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB2162946B (en) | 1987-10-14 |
| GB8420053D0 (en) | 1984-09-12 |
| US4729950A (en) | 1988-03-08 |
| DE3528391A1 (de) | 1986-02-20 |
| GB2162946A (en) | 1986-02-12 |
| DE3528391C2 (de) | 1996-01-11 |
| JPS6154453A (ja) | 1986-03-18 |
| GB8519544D0 (en) | 1985-09-11 |
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