US4247631A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Reagent and method for the analytic determination of hydrogen peroxide
Assignee: COOPERBIOMEDICAL Inc 3145 PORTER DRIVE PALO ALTO CA 94304 A CORP OF
•
Filing: 1979-01-31
•
Granted: 1981-01-27
•
Expires: 1999-01-31
Abstract
Abstract A 3-aminobenzoic acid or a 3-aminobenzenesulfonic acid, when reacted with a 4-aminoantipyrine in aqueous medium in the presence of hydrogen peroxide forms a novel colored dye which is believed to be a charge-transfer complex of free radicals formed from the 3-aminoaromatic acid and the 4-aminoantipyrine. The dye and the process by which it is produced are useful in analytical procedures for hydrogen peroxide, as well as in enzymatic analyses involving the formation of hydrogen peroxide.
Inventors
- 👤 Paul T. Nix
- 👤 Spencer Fields
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 15:45
CPC Classifications
C; C12; C12Q; C12Q1/00; C12Q1/62; C12Q1/26; C12Q1/28; C12Q1/54; C12Q1/60; C12Q2326/00; C12Q2326/90; C12Q2326/96; Y; Y10; Y10S; Y10S435/00; Y10S435/81; Y10T; Y10T436/00; Y10T436/20
Claims Analysis
Total Claims: 41
Claim 1
Independent Claim
137 words
A method for producing a dye comprising contacting, in an aqueous medium at a temperature of from about 20° to about 45° C., having a pH of from about 3 to about 9.5, and containing hydrogen peroxide, (1) peroxidase, (2) an amino-aromatic acid represented by the formula: ##STR7## wherein X is a mono- or dialkylamino group, and ZH is the carboxyl group or the sulfo group, and (3) a 4-aminoantipyrine represented by the formula: ##STR8## wherein each of R and R 1 , when taken separately, is alkyl, R 2 is an aromatic moiety, each of R 3 and R 4 , when taken separately, is hydrogen or alkyl, and Y is oxygen or sulfur, wherein the molar ratio of said aminoaromatic acid to said aminoantipyrine is in th range of from bout 0.1:1 to about 25:1.
Claim 2
Independent Claim
137 words
A method for producing a dye comprising contacting, in an aqueous medium at a temperature of from about 20° to about 45° C., having a pH of from about 3 to about 9.5, and containing hydrogen peroxide, (1) peroxidase, (2) an amino-aromatic acid represented by the formula: ##STR7## wherein X is a mono- or dialkylamino group, and ZH is the carboxyl group or the sulfo group, and (3) a 4-aminoantipyrine represented by the formula: ##STR8## wherein each of R and R 1 , when taken separately, is alkyl, R 2 is an aromatic moiety, each of R 3 and R 4 , when taken separately, is hydrogen or alkyl, and Y is oxygen or sulfur, wherein the molar ratio of said aminoaromatic acid to said aminoantipyrine is in th range of from bout 0.1:1 to about 25:1.
Claim 3
Dependent Claim
28 words
A method according to claim 1 wherein said aminoaromatic acid is an aminobenzoic acid and said aminoantipyrine is one wherein R 2 is phenyl and Y is oxygen.
Claim 4
Dependent Claim
19 words
A method according to claim 2 wherein said aminoantipyrine is one wherein R and R 1 each is methyl.
Claim 5
Dependent Claim
13 words
A method according to claim 3 wherein said aminobenzoic acid is 3-(N,N-dimethylamino)benzoic acid.
Claim 6
Dependent Claim
21 words
A method according to claim 4 wherein said aminoantipyrine is one wherein each of R 3 and R 4 is hydrogen.
Claim 7
Dependent Claim
21 words
A method according to claim 4 wherein said aminoantripyrine is one wherein each of R 3 and R 4 is methyl.
Claim 8
Dependent Claim
28 words
A method according to claim 5 wherein the molar ratio of said 3-(N,N-dimethylamino)benzoic acid to said aminoantipyrine is in the range of from about 8:1 to about 12:1.
Claim 9
Independent Claim
152 words
A method for detecting the presence of hydrogen peroxide in an aqueous medium at a temperature of from about 20° C. to about 45° C. and having a pH of from about 3 to about 9.5, which comprises: (a) adding to said aqueous medium (1) peroxidase, (2) an aminoaromatic acid represented by the formula: ##STR9## wherein X is a mono-or dialkylamine group and ZH is the carboxyl group or the sulfo group, and (3) a 4-aminoantipyrine represented by the formula: ##STR10## wherein each of R and R 1 , when taken separately, is alkyl, R 2 is an aromatic moiety, each of R 3 and R 4 , when taken separately, is hydrogen or alkyl, and Y is oxygen or sulfur, wherein the molar ratio of said aminoaromatic acid to said aminoantipyrine is in the range of from about 0.1:1 to about 25:1; and (b) thereafter measuring any resulting color change photometrically.
Claim 10
Independent Claim
152 words
A method for detecting the presence of hydrogen peroxide in an aqueous medium at a temperature of from about 20° C. to about 45° C. and having a pH of from about 3 to about 9.5, which comprises: (a) adding to said aqueous medium (1) peroxidase, (2) an aminoaromatic acid represented by the formula: ##STR9## wherein X is a mono-or dialkylamine group and ZH is the carboxyl group or the sulfo group, and (3) a 4-aminoantipyrine represented by the formula: ##STR10## wherein each of R and R 1 , when taken separately, is alkyl, R 2 is an aromatic moiety, each of R 3 and R 4 , when taken separately, is hydrogen or alkyl, and Y is oxygen or sulfur, wherein the molar ratio of said aminoaromatic acid to said aminoantipyrine is in the range of from about 0.1:1 to about 25:1; and (b) thereafter measuring any resulting color change photometrically.
Claim 11
Dependent Claim
28 words
A method according to claim 8 wherein said aminoaromatic acid is an aminobenzoic acid and said aminoantipyrine is one wherein R 2 is phenyl and Y is oxygen.
Claim 12
Dependent Claim
20 words
A method according to claim 9 wherein said aminoantipyrine is one wherein each of R and R 1 is methyl.
Claim 13
Dependent Claim
13 words
A method according to claim 10 wherein said aminobenzoic acid is 3-(N,N-dimethylamino)benzoic acid.
Claim 14
Dependent Claim
21 words
A method according to claim 11 wherein said aminoantipyrine is one wherein each of R 3 and R 4 is hydrogen.
Claim 15
Dependent Claim
21 words
A method according to claim 11 wherein said aminoantipyrine is one wherein each of R 3 and R 4 is methyl.
Claim 16
Dependent Claim
28 words
A method according to claim 12 wherein the molar ratio of said 3-(N,N-dimethylamino)-benzoic acid to said aminoantipyrine is in the range of from about 8:1 to about 12:1.
Claim 17
Dependent Claim
196 words
In a method for the enzymatic determination of the amount of a component in a body fluid by admixing said fluid with (a) an enzyme capable of promoting the oxidation of said component and forming hydrogen peroxide, (b) peroxidase, and (c) a chromagen capable of being oxidized by peroxidasecatalyzed reaction with hydrogen peroxide to form a chromophore, and measuring the resulting color change, the improvement wherein said chromogen is a mixture of (1) an aminoaromatic acid represented by the formula: ##STR11## wherein X is a mono- or dialkyl amine group and ZH is the carboxyl or the sulfo group and (2) a 4-aminoantipyrine represented by the formula: ##STR12## wherein each of R and R 1 , when taken separately, is alkyl, R 2 is an aromatic moiety, each of R 3 and R 4 , when taken separately, is hydrogen or alkyl, and Y is oxygen or sulfur, wherein the molar ratio of said aminoaromatic acid to said aminoantipyrine is in the range of from about 0.1:1 to about 25:1, said method being conducted at a temperture of from about 20° C. to about 45° C., and a pH of from about 3 to about 9.5.
Claim 18
Dependent Claim
196 words
In a method for the enzymatic determination of the amount of a component in a body fluid by admixing said fluid with (a) an enzyme capable of promoting the oxidation of said component and forming hydrogen peroxide, (b) peroxidase, and (c) a chromagen capable of being oxidized by peroxidasecatalyzed reaction with hydrogen peroxide to form a chromophore, and measuring the resulting color change, the improvement wherein said chromogen is a mixture of (1) an aminoaromatic acid represented by the formula: ##STR11## wherein X is a mono- or dialkyl amine group and ZH is the carboxyl or the sulfo group and (2) a 4-aminoantipyrine represented by the formula: ##STR12## wherein each of R and R 1 , when taken separately, is alkyl, R 2 is an aromatic moiety, each of R 3 and R 4 , when taken separately, is hydrogen or alkyl, and Y is oxygen or sulfur, wherein the molar ratio of said aminoaromatic acid to said aminoantipyrine is in the range of from about 0.1:1 to about 25:1, said method being conducted at a temperture of from about 20° C. to about 45° C., and a pH of from about 3 to about 9.5.
Claim 19
Dependent Claim
28 words
A method according to claim 15 wherein said aminoaromatic acid is an aminobenzoic acid and said aminoantipyrine is one wherein R 2 is phenyl and Y is oxygen.
Claim 20
Dependent Claim
20 words
A method according to claim 16 wherein sid aminoantipyrine is one wherein each of R and R 1 is methyl.
Claim 21
Dependent Claim
13 words
A method according to claim 17 wherein said aminobenzoic acid is 3-(N,N-dimethylamino)benzoic acid.
Claim 22
Dependent Claim
21 words
A method according to claim 18 wherein said aminoantipyrine is one wherein each of R 3 and R 4 is hydrogen.
Claim 23
Dependent Claim
21 words
A method according to claim 18 wherein said aminoantipyrine is one wherein each of R 3 and R 4 is methyl.
Claim 24
Dependent Claim
28 words
A method according to claim 19 wherein the molar ratio of said 3-(N,N-dimethylamino)-benzoic acid to said aminoantipyrine is in the range of from about 8:1 to about 12:1.
Claim 25
Dependent Claim
18 words
A method according to claim 15 wherein said enzyme capable of promoting oxidation of said component is uricase.
Claim 26
Dependent Claim
19 words
A method according to claim 15 wherein said enzyme capable of promoting oxidation of said component is glucose oxidase.
Claim 27
Dependent Claim
19 words
A method according to claim 15 wherein said enzyme capable of promoting oxidation of said component is cholesterol oxidase.
Claim 28
Dependent Claim
111 words
A reagent system for detecting the presence of hydrogen peroxide in an aqueous medium comprising: (1) peroxidase, (2) an aminoaromatic acid represented by the formula: ##STR13## wherein X is a mono- or dialkylamino group and ZH is the carboxyl group or the sulfo group, and (3) a 4-aminoantipyrine represented by the formula: ##STR14## wherein each of R and R 1 , when taken separately, is alkyl, R 2 is an aromatic moiety, each of R 3 and R 4 , when taken separately, is hydrogen or alkyl, and Y is oxygen or sulfur, wherein the molar ratio of said aminoaromatic acid to said aminoantipyrine is from about 0.1:1 to about 25:1.
Claim 29
Dependent Claim
111 words
A reagent system for detecting the presence of hydrogen peroxide in an aqueous medium comprising: (1) peroxidase, (2) an aminoaromatic acid represented by the formula: ##STR13## wherein X is a mono- or dialkylamino group and ZH is the carboxyl group or the sulfo group, and (3) a 4-aminoantipyrine represented by the formula: ##STR14## wherein each of R and R 1 , when taken separately, is alkyl, R 2 is an aromatic moiety, each of R 3 and R 4 , when taken separately, is hydrogen or alkyl, and Y is oxygen or sulfur, wherein the molar ratio of said aminoaromatic acid to said aminoantipyrine is from about 0.1:1 to about 25:1.
Claim 30
Dependent Claim
35 words
A system according to claim 25 additionally including a buffer to buffer an aqueous solution of said peroxidase, aminoaromatic acid and aminoantipyrine to a pH in the range of from about 3 to about 9.5.
Claim 31
Dependent Claim
25 words
A system according to claim 26 additionally including an enzyme capable of supporting oxidation of a component of a body fluid to form hydrogen peroxide.
Claim 32
Dependent Claim
25 words
A system according to claim 27 wherein said enzyme is capable of supporting the oxidation of uric acid, cholesterol or glucose to form hydrogen peroxide.
Claim 33
Dependent Claim
18 words
A system according to claim 27 wherein ZH is carboxyl, R 2 is phenyl and Y is oxygen.
Claim 34
Dependent Claim
18 words
A system according to claim 29 wherein X is aminoalkyl, R is methyl and R 1 is methyl.
Claim 35
Dependent Claim
19 words
A system according to claim 30 wherein X is dimethylamino and R 3 and R 4 each is methyl.
Claim 36
Dependent Claim
19 words
A system according to claim 30 wherein X is dimethylamino and R 3 and R 4 each is hydrogen.
Claim 37
Dependent Claim
28 words
A system according to claim 32 wherein the molar ratio of said aminoaromatic acid to said aminoantipyrine is in the range of from about 8:1 to about 12:1.
Claim 38
Dependent Claim
15 words
A system according to claim 33 wherein said enzyme capable of supporting oxidation is uricase.
Claim 39
Dependent Claim
16 words
A system according to claim 33 wherein said enzyme capable of supporting oxidation is glucose oxidase.
Claim 40
Dependent Claim
16 words
A system according to claim 33 wherein said enzyme capable of supporting oxidation is cholesterol oxidase.
Claim 41
Dependent Claim
9 words
The system according to claim 25 in kit form.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-01-27 | 1984-07-28 | 1985-01-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-01-27 | 1988-07-28 | 1989-01-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-01-27 | 1992-07-28 | 1993-01-27 | $7700.00 | Window Closed / Lapsed |