EP0455471A2
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EP
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Improved chemiluminescent reagents and methods
Assignee: Resonac Corp
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Filing: 1991-04-30
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Granted: —
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Expires: 2011-04-30
Abstract
Abstract New and improved enhancers for intensifying light emission in chemiluminescence or chemiluminometric assays are disclosed. These enhancers are phenols substituted in the ortho- or para-position by a five-membered sulfur-containing aromatic ring. Thus, these enhancers are ortho- or para-substituted phenols wherein the ortho- or para-substituent is of the formula: wherein each X is independently CR or N, wherein R is H or a moiety selected from the group consisting of R′, OR′, SR′, NHR′, NR′₂ and halo, wherein each R′ is independently alkyl(1-6C); or wherein adjacent X=X may be substituted with -CR=CR-CR=CR-, wherein each R is H or a moiety as defined above. These enhancers, as well as enhancers known in the art can be supplied either per se or in blocked form as esters of picolinic or isonicotinic acid.
Inventors
- 👤 Steven Torkelson
- 👤 Naomi Kameda
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-09 02:33
CPC Classifications
C; C07; C07D; C07D409/00; C07D409/02; C07D409/12; C07D417/00; C07D417/02; C07D417/12; C12; C12Q; C12Q1/00; C12Q1/26; C12Q1/28; G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/52
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
111 words
In a luminescent or luminometric assay which comprises conducting a chemiluminescent reaction using an oxidation catalyst, an oxidant, and a chemiluminescent 2,3-dihydro-1,4-phthalazinedione, and measuring or detecting the chemiluminescence thereby produced, the improvement wherein the reaction is carried out in the presence of an ortho- or para-substituted phenolic enhancer wherein the ortho- or para-substituent is of the formula wherein each X is independently CR or N; wherein R is H or a moiety selected from the group consisting of R′, OR′, SR′, NHR′, NR′₂ and halo, wherein each R′ is independently alkyl(1-6C); or wherein adjacent X=X may be substituted with -CR=CR-CR=CR-, wherein each R is H or a moiety as defined above.
Claim 2
Dependent Claim
39 words
The assay of claim 1 wherein said substituent is in the para-position; and wherein the substituent of formula 1 has the formula: wherein the substituent of formula 2 has the formula: wherein R is as defined in claim 1.
Claim 3
Dependent Claim
35 words
The assay of claim 2 wherein the substituent of formula 1a and 1c have the formulas: wherein the substituent of formulas 2a and 2d have the formulas: wherein R is defined as in claim 1.
Claim 4
Dependent Claim
19 words
The assay of any one of claims 1 to 3 wherein each R is independently H or alkyl (1-6C).
Claim 5
Dependent Claim
27 words
The assay of any one of claims 2 to 4 wherein said p-substituted phenolic enhancer is selected from the group consisting of 4-(2′-thienyl)phenol, 4-[4′-(2′-methyl)thiazolyl]phenol, 4-[2′-(4′-methyl)-thiazolyl]phenol, and 4-(2′-benzothiazolyl)phenol.
Claim 6
Dependent Claim
88 words
A composition useful to prepare a substrate reagent for a chemiluminescence-based reaction, which composition comprises a chemiluminescent 2,3-dihydro-1,4-phthalazinedione and an ortho- or para-substituted phenolic enhancer wherein the ortho- or para-substituent is of the formula wherein each X is independently CR or N, wherein R is H or a moiety selected from the group consisting of R′, OR′, SR′, NHR′, NR′₂ and halo, wherein each R′ is independently alkyl(1-6C); or wherein adjacent X=X may be substituted with -CR=CR-CR=CR-, wherein each R is H or a moiety as defined above.
Claim 7
Dependent Claim
39 words
The composition of claim 6 wherein said substituent is in the para-position; and wherein the substituent of formula 1 has the formula: wherein the substituent of formula 2 has the formula: wherein R is as defined in claim 1.
Claim 8
Dependent Claim
35 words
The composition of claim 7 wherein the substituent of formula 1a and 1c have the formulas: wherein the substituent of formulas 2a and 2d have the formulas: wherein R is defined as in claim 7.
Claim 9
Dependent Claim
19 words
The composition of any one of claims 6 to 8 wherein each R is independently H or alkyl (1-6C).
Claim 10
Dependent Claim
27 words
The composition of any one of claims 7 to 9 wherein said p-substituted phenolic enhancer is selected from the group consisting of 2-(4′-hydroxyphenyl)thiophene, 4-[4′-(2′-methyl)thiazolyl]phenol, 4-[2′-(4′-methyl)thiazolyl]phenol, and 2-(4′-hydroxyphenyl)-benzothiazole.
Claim 11
Dependent Claim
49 words
A blocked enhancer useful in enhancing the emission of light in a luminescent or a luminometric assay which is an ester formed by a compound of the formula: and an alcohol which is the ortho- or para-substituted phenolic enhancer set forth in any one of claims 1 to 5.
Claim 12
Dependent Claim
67 words
In a luminescent or luminometric assay which comprises conducting a chemiluminescent reaction using an oxidation catalyst, an oxidant, and a chemiluminescent 2,3-dihydro-1,4-phthalazinedione, and measuring or detecting the chemiluminescence thereby produced, the improvement wherein the reaction is carried out in the presence of a blocked enhancer which is an ester formed from an acid of the formula: wherein R˝ is optionally substituted alkyl (1-6C), with a phenolic enhancer.
Claim 13
Dependent Claim
36 words
The assay of claim 12 wherein the phenolic enhancer is selected from the group consisting of p-phenyl phenol, p-iodophenol, 2,4-dibromophenol, 2,4-dichlorophenol, p-hydroxybenzoic acid, p-hydroxycinnamic acid, and the phenolic enhancer of any one of claims 1to 5.
Claim 14
Dependent Claim
22 words
The assay of claim 13 wherein the phenolic enhancer is selected from the group consisting of 4-(2′-thienyl)phenol, 4-[4′-(2′-methyl)thiazolyl] phenol, 4-[2′-(4′-methyl)thiazolyl]phenol and 4-(2′-benzothiazolyl)phenol.
Claim 15
Dependent Claim
46 words
A composition useful to prepare a substrate reagent for a chemiluminescence-based reaction, which composition comprises a chemiluminescent 2,3-dihydro-1,4-phthalazinedione and a blocked enhancer which is an ester formed from an acid of the formula: wherein R˝ is an optionally substituted alkyl substituent (1-6C), with a phenolic enhancer.
References Cited (Backward Citations)
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