Patent US4828983A successfully refreshed from Google Patents.
US4828983A
Expired / Lapsed
US
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Use of phenols and anilines to increase the rate of peroxidase catalyzed oxidation of leuco dyes
Assignee: Clinical Diagnostic Systems Inc
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Filing: 1986-07-10
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Granted: 1989-05-09
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Expires: 2006-07-10
Abstract
Abstract Certain phenols and anilines can be used as electron transfer agents to increase the rate of oxidation of leuco dyes by peroxidase. These phenols and anilines can react with hydrogen peroxide in the presence of peroxidase to provide intermediates which have higher oxidation potentials than the slowly oxidized substrates, e.g. the leuco dyes. These phenols and anilines can be used to advantage in both solution and dry assays of various analytes. They are particularly useful for the determination of an immunologically reactive ligand in an immunoassay.
Inventors
- 👤 Gregory J. McClune
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 20:19
CPC Classifications
C; C12; C12Q; C12Q1/00; C12Q1/26; C12Q1/28; G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/58; G01N33/581
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
90 words
An analytical composition comprising peroxidase or a peroxidase-labeled analog of an immunologically reactive ligand, an imidazole or triarylmethane leuco dye which is capable of providing a detectable dye in the presence of peroxidase and hydrogen peroxide, and a phenol or aniline electron transfer agent which is capable of reacting with hydrogen peroxide in the presence of peroxidase to provide an intermediate compound which has a higher oxidation potential than said leuco dye, said phenol or aniline electron transfer agent being p, p'-biphenol, 4'-hydroxyacetanilide, p-methoxyphenol, o-methoxyphenol, p-anisidine, p-hydroxy-N, N'-dimethyl-aniline or o-phenylenediamine.
Claim 2
Dependent Claim
90 words
An analytical composition comprising peroxidase or a peroxidase-labeled analog of an immunologically reactive ligand, an imidazole or triarylmethane leuco dye which is capable of providing a detectable dye in the presence of peroxidase and hydrogen peroxide, and a phenol or aniline electron transfer agent which is capable of reacting with hydrogen peroxide in the presence of peroxidase to provide an intermediate compound which has a higher oxidation potential than said leuco dye, said phenol or aniline electron transfer agent being p, p'-biphenol, 4'-hydroxyacetanilide, p-methoxyphenol, o-methoxyphenol, p-anisidine, p-hydroxy-N, N'-dimethyl-aniline or o-phenylenediamine.
Claim 3
Dependent Claim
13 words
The composition of claim 1 wherein said leuco dye is an imidazole derivative.
Claim 4
Dependent Claim
12 words
The composition of claim 2 wherein said imidazole derivative is a triarylimidazole.
Claim 5
Dependent Claim
15 words
The composition of claim 1 wherein said phenol or aniline electron transfer agent is 4'-hydroxy-acetanilide.
Claim 6
Dependent Claim
22 words
The composition of claim 1 further comprising an interactive composition which is capable of interacting with an analyte to provide hydrogen peroxide.
Claim 7
Dependent Claim
22 words
The composition of claim 1 comprising peroxidase and an analog of an immunologically reactive ligand labeled with an enzyme other than peroxidase.
Claim 8
Dependent Claim
12 words
The composition of claim 6 wherein said ligand analog comprises glucose oxidase.
Claim 9
Dependent Claim
96 words
An analytical element comprising an absorbent carrier material containing: peroxidase or a peroxidase labeled analog of an immunologically reactive ligand, an imidazole or triarylmethane leuco dye which is capable of providing a detectable dye in the presence of peroxidase and hydrogen peroxide, and a phenol or aniline electron transfer agent which is capable of reacting with hydrogen peroxide in the presence of peroxidase to provide an intermediate compound which has a higher oxidation potential than said leuco dye, said phenol or aniline electron transfer agent being p, p'-biphenol, 4'-hydroxyacetanilide, p-methoxyphenol, o-methoxyphenol, p-anisidine, p-hydroxy-N, N'-dimethyl-aniline or o-phenylenediamine.
Claim 10
Dependent Claim
96 words
An analytical element comprising an absorbent carrier material containing: peroxidase or a peroxidase labeled analog of an immunologically reactive ligand, an imidazole or triarylmethane leuco dye which is capable of providing a detectable dye in the presence of peroxidase and hydrogen peroxide, and a phenol or aniline electron transfer agent which is capable of reacting with hydrogen peroxide in the presence of peroxidase to provide an intermediate compound which has a higher oxidation potential than said leuco dye, said phenol or aniline electron transfer agent being p, p'-biphenol, 4'-hydroxyacetanilide, p-methoxyphenol, o-methoxyphenol, p-anisidine, p-hydroxy-N, N'-dimethyl-aniline or o-phenylenediamine.
Claim 11
Dependent Claim
112 words
An analytical element comprising a support having thereon a registration zone and a porous spreading zone, said element further comprising, independently in any of said zones, peroxidase or a peroxidase-labeled analog of an immunologically reactive ligand, an imidazole or triarylmethane leuco dye which is capable of providing a detectable dye in the presence of peroxidase and hydrogen peroxide, and a phenol or aniline electron transfer agent which is capable of reacting with hydrogen peroxide in the presence of peroxidase to provide an intermediate compound which has a higher oxidation potential than said leuco dye, said phenol or aniline electron transfer agent being p, p'-biphenol, 4'-hydroxyacetanilide, p-methoxyphenol, o-methoxyphenol, p-anisidine, p-hydroxy-N, N'-dimethyl-aniline or o-phenylenediamine.
Claim 12
Dependent Claim
112 words
An analytical element comprising a support having thereon a registration zone and a porous spreading zone, said element further comprising, independently in any of said zones, peroxidase or a peroxidase-labeled analog of an immunologically reactive ligand, an imidazole or triarylmethane leuco dye which is capable of providing a detectable dye in the presence of peroxidase and hydrogen peroxide, and a phenol or aniline electron transfer agent which is capable of reacting with hydrogen peroxide in the presence of peroxidase to provide an intermediate compound which has a higher oxidation potential than said leuco dye, said phenol or aniline electron transfer agent being p, p'-biphenol, 4'-hydroxyacetanilide, p-methoxyphenol, o-methoxyphenol, p-anisidine, p-hydroxy-N, N'-dimethyl-aniline or o-phenylenediamine.
Claim 13
Dependent Claim
19 words
The element of claim 9 comprising said peroxidase and phenol or aniline electron transfer agent in said registration zone.
Claim 14
Dependent Claim
12 words
The element of claim 9 wherein said zones are individually superposed layers.
Claim 15
Dependent Claim
22 words
The element of claim 9 further comprising an interactive composition which is capable of interacting with an analyte to provide hydrogen peroxide.
Claim 16
Dependent Claim
13 words
The element of claim 9 wherein said leuco dye is an imidazole derivative.
Claim 17
Dependent Claim
22 words
The element of claim 9 comprising peroxidase and an analog of an immunologically reactive ligand labeled with an enzyme other than peroxidase.
Claim 18
Dependent Claim
22 words
The element of claim 9 wherein said phenol or aniline electron transfer agent is 4'-hydroxyacetanilide and said leuco dye is 2-(3,5-dimethoxy-4-hydroxyphenyl)-4,5-bis(4-dimethylaminophenyl) imidazole.
Claim 19
Dependent Claim
14 words
The element of claim 9 further comprising a receptor for an immunologically reactive ligand.
Claim 20
Independent Claim
126 words
A method for the determination of an analyte comprising the steps of: A. contacting a sample of a liquid suspected of containing an analyte with: peroxidase or a peroxidase-labeled analog of an immunologically reactive ligand, an imidazole or triarylmethane leuco dye which is capable of providing a detectable dye in the presence of peroxidase and hydrogen peroxide, and a phenol or aniline electron transfer agent which is capable of reacting with hydrogen peroxide in the presence of peroxidase to provide an intermediate compound which has a higher oxidation potential than said leuco dye, said phenol or aniline electron transfer agent being p, p'-biphenol, 4'-hydroxyacetanilide, p-methoxyphenol, o-methoxyphenol, p-anisidine, p-hydroxy-N, N'-dimethyl-aniline or o-phenylenediamine, and B. determining said detectable dye as a result of the presence of said analyte.
Claim 21
Independent Claim
126 words
A method for the determination of an analyte comprising the steps of: A. contacting a sample of a liquid suspected of containing an analyte with: peroxidase or a peroxidase-labeled analog of an immunologically reactive ligand, an imidazole or triarylmethane leuco dye which is capable of providing a detectable dye in the presence of peroxidase and hydrogen peroxide, and a phenol or aniline electron transfer agent which is capable of reacting with hydrogen peroxide in the presence of peroxidase to provide an intermediate compound which has a higher oxidation potential than said leuco dye, said phenol or aniline electron transfer agent being p, p'-biphenol, 4'-hydroxyacetanilide, p-methoxyphenol, o-methoxyphenol, p-anisidine, p-hydroxy-N, N'-dimethyl-aniline or o-phenylenediamine, and B. determining said detectable dye as a result of the presence of said analyte.
Claim 22
Dependent Claim
38 words
The method of claim 17 for the determination of an analyte other than hydrogen peroxide wherein said liquid sample is also contacted with an interactive composition which is capable of reacting with said analyte to provide hydrogen peroxide.
Claim 23
Dependent Claim
24 words
The method of claim 17 for the determination of an immunologically reactive ligand carried out in the presence of a receptor for said ligand.
Claim 24
Dependent Claim
16 words
The method of claim 19 carried out with a peroxidase-labeled analog of said immunologically reactive ligand.
Claim 25
Dependent Claim
24 words
The method of claim 19 carried out with peroxidase and an analog of said immunologically reactive ligand labeled with an enzyme other than peroxidase.
Claim 26
Dependent Claim
15 words
The method of claim 17 wherein said phenol or aniline electron transfer agent is 4'-hydroxyacet-anilide.
Claim 27
Dependent Claim
33 words
The method of claim 17 carried out with an analytical element comprising an absorbent carrier material containing said peroxidase or peroxidase-labeled analog, said imidazole or triarylmethane leuco dye and said electron transfer agent.
Claim 28
Dependent Claim
17 words
The method of claim 17 for the determination of glucose, triglycerides, uric acid, cholesterol or creatine kinase.
Claim 29
Dependent Claim
76 words
A leuco dye composition comprising an imidazole or triarylmethane leuco dye which is capable of providing a detectable dye in the presence of peroxidase and hydrogen peroxide, and a phenol or aniline electron transfer agent which is capable of reacting with hydrogen peroxide to provide an intermediate compound which has a higher oxidation potential than said leuco dye, said phenol or aniline electron transfer agent being p, p'-biphenol, 4'-hydroxyacetanilide, p-methoxyphenol, o-methoxyphenol, p-anisidine, p-hydroxy-N, N'-dimethylaniline or o-phenylenediamine.
Claim 30
Dependent Claim
76 words
A leuco dye composition comprising an imidazole or triarylmethane leuco dye which is capable of providing a detectable dye in the presence of peroxidase and hydrogen peroxide, and a phenol or aniline electron transfer agent which is capable of reacting with hydrogen peroxide to provide an intermediate compound which has a higher oxidation potential than said leuco dye, said phenol or aniline electron transfer agent being p, p'-biphenol, 4'-hydroxyacetanilide, p-methoxyphenol, o-methoxyphenol, p-anisidine, p-hydroxy-N, N'-dimethylaniline or o-phenylenediamine.
Claim 31
Dependent Claim
14 words
The leuco dye composition of claim 25 wherein said electron transfer agent is 4'-hydroxyacetanilide.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-05-08 | 1992-11-07 | 1993-05-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-05-08 | 1996-11-07 | 1997-05-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-05-08 | 2000-11-07 | 2001-05-09 | $7700.00 | Window Closed / Lapsed |