DE3528391C2 - Lumineszenz- oder luminometrischer Assay - Google Patents
Lumineszenz- oder luminometrischer AssayInfo
- Publication number
- DE3528391C2 DE3528391C2 DE3528391A DE3528391A DE3528391C2 DE 3528391 C2 DE3528391 C2 DE 3528391C2 DE 3528391 A DE3528391 A DE 3528391A DE 3528391 A DE3528391 A DE 3528391A DE 3528391 C2 DE3528391 C2 DE 3528391C2
- Authority
- DE
- Germany
- Prior art keywords
- amino
- assay
- peroxidase
- chemiluminescent
- reaction
- 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 - Fee Related
Links
- 238000003556 assay Methods 0.000 title claims description 55
- 238000004020 luminiscence type Methods 0.000 title claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 53
- 102000003992 Peroxidases Human genes 0.000 claims description 51
- 108040007629 peroxidase activity proteins Proteins 0.000 claims description 33
- 239000000126 substance Substances 0.000 claims description 33
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- HWYHZTIRURJOHG-UHFFFAOYSA-N luminol Chemical compound O=C1NNC(=O)C2=C1C(N)=CC=C2 HWYHZTIRURJOHG-UHFFFAOYSA-N 0.000 claims description 21
- HUDPLKWXRLNSPC-UHFFFAOYSA-N 4-aminophthalhydrazide Chemical compound O=C1NNC(=O)C=2C1=CC(N)=CC=2 HUDPLKWXRLNSPC-UHFFFAOYSA-N 0.000 claims description 17
- 239000007800 oxidant agent Substances 0.000 claims description 15
- 150000004982 aromatic amines Chemical class 0.000 claims description 14
- 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 13
- 102000004190 Enzymes Human genes 0.000 claims description 12
- 108090000790 Enzymes Proteins 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 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 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 5
- 238000005259 measurement Methods 0.000 claims description 5
- 125000005605 benzo group Chemical group 0.000 claims description 3
- FIIDVVUUWRJXLF-UHFFFAOYSA-N 4-phenylmethoxyaniline Chemical compound C1=CC(N)=CC=C1OCC1=CC=CC=C1 FIIDVVUUWRJXLF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 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 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 claims description 2
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- 229940072417 peroxidase Drugs 0.000 description 35
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 34
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- 238000000034 method Methods 0.000 description 19
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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 11
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- 125000003277 amino group Chemical group 0.000 description 9
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 9
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- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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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 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
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- 239000006228 supernatant Substances 0.000 description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
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- 239000003054 catalyst Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
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- 150000007523 nucleic acids Chemical class 0.000 description 3
- 108020004707 nucleic acids Proteins 0.000 description 3
- 102000039446 nucleic acids Human genes 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
- 235000013824 polyphenols Nutrition 0.000 description 3
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- 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
- RNIPJYFZGXJSDD-UHFFFAOYSA-N 2,4,5-triphenyl-1h-imidazole Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 RNIPJYFZGXJSDD-UHFFFAOYSA-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
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 239000000275 Adrenocorticotropic Hormone Substances 0.000 description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 102000009151 Luteinizing Hormone Human genes 0.000 description 2
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Classifications
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- 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
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- 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
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- 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)
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- Biomedical Technology (AREA)
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- Biophysics (AREA)
- Pathology (AREA)
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- 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848420053A GB8420053D0 (en) | 1984-08-07 | 1984-08-07 | Enhanced luminescent/luminometric assay |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3528391A1 DE3528391A1 (de) | 1986-02-20 |
| DE3528391C2 true DE3528391C2 (de) | 1996-01-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3528391A Expired - Fee Related DE3528391C2 (de) | 1984-08-07 | 1985-08-07 | Lumineszenz- oder luminometrischer Assay |
Country Status (4)
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4794073A (en) * | 1985-07-10 | 1988-12-27 | Molecular Diagnostics, Inc. | Detection of nucleic acid hybrids by prolonged chemiluminescence |
| US4853327A (en) * | 1985-07-10 | 1989-08-01 | Molecular Diagnostics, Inc. | Enhanced phthalazinedione chemiluminescence |
| CA1307480C (en) * | 1985-07-10 | 1992-09-15 | Nanibhushan Dattagupta | 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 |
| EP0361470B1 (en) * | 1988-09-30 | 1993-12-22 | Fujirebio Inc. | Method for the chemiluminescence assay of the activity of peroxidase |
| EP0384271B1 (en) * | 1989-02-14 | 1996-05-08 | Wako Pure Chemical Industries Ltd | Method for enhancement of chemiluminescence |
| EP0422252B1 (en) * | 1989-04-28 | 1995-07-26 | Toray Industries, Inc. | Method for detecting a substance using chemiluminescence |
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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 |
| EP0116454B1 (en) * | 1983-02-11 | 1987-04-29 | National Research Development Corporation | 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 |
|---|---|
| GB2162946A (en) | 1986-02-12 |
| US4729950A (en) | 1988-03-08 |
| GB8519544D0 (en) | 1985-09-11 |
| JPH0553478B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-08-10 |
| JPS6154453A (ja) | 1986-03-18 |
| GB2162946B (en) | 1987-10-14 |
| GB8420053D0 (en) | 1984-09-12 |
| DE3528391A1 (de) | 1986-02-20 |
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