US4745181A
Expired / Lapsed
US
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Polysubstituted aryl acridinium esters
Assignee: Bayer Corp
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Filing: 1986-10-06
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Granted: 1988-05-17
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Expires: 2006-10-06
Abstract
Abstract The present invention relates to novel acridinium esters which are useful as luminescent labels in specific binding assays such as immunoassays or nucleic acid hybridization assays. More particularly, polysubstituted aryl acridinium esters are highly stable labels for use in a chemiluminescent immunoassay.
Inventors
- 👤 Say-Jong Law
- 👤 Steve C. S. Chang
- 👤 Stephen A. Palmacci
- 👤 Roger S. Cubicciotti
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 12:00
CPC Classifications
C; C07; C07D; C07D219/00; C07D219/04; Y; Y10; Y10S; Y10S530/00; Y10S530/802
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
190 words
A luminescent conjugate for use in luminescent assays comprising a polysubstituted aryl acridinum ester of the formula: ##STR4## where R 1 is an alkyl, alkenyl, alkynyl, or aryl group; R 2 , R 3 , R 5 , or R 7 are a hydrogen, amino, carboxyl, hydroxyl, alkoxyl, nitro, or halide group; R 4 or R 8 are an alkyl, alkenyl, alkynyl, aryl, alkoxyl, amino, amido, sulfonamido, or sulfide group; R 6 represents the following substituent: R.sub.6 =-R.sub.9 -R.sub.10 where R 9 is not required but optionally can be an alkyl, aryl, or aralkyl group, and R 10 is selected from the following: ##STR5## X is CH 3 SO4 - , OSO 2 F - , a halide, OSO 2 CF 3 - , OSO 2 C 4 F 9 - , ##STR6## R is alkyl, aryl, aralkyl; and finally R 5 , R 6 , and R 7 substituent positions on the phenoxy ring are interchangeable, wherein the R 6 substituent of the polysubstituted aryl acridinium ester is covalently coupled to a molecule with biological activity which molecule is capable of being covalently coupled to the R 6 substituent.
Claim 2
Dependent Claim
190 words
A luminescent conjugate for use in luminescent assays comprising a polysubstituted aryl acridinum ester of the formula: ##STR4## where R 1 is an alkyl, alkenyl, alkynyl, or aryl group; R 2 , R 3 , R 5 , or R 7 are a hydrogen, amino, carboxyl, hydroxyl, alkoxyl, nitro, or halide group; R 4 or R 8 are an alkyl, alkenyl, alkynyl, aryl, alkoxyl, amino, amido, sulfonamido, or sulfide group; R 6 represents the following substituent: R.sub.6 =-R.sub.9 -R.sub.10 where R 9 is not required but optionally can be an alkyl, aryl, or aralkyl group, and R 10 is selected from the following: ##STR5## X is CH 3 SO4 - , OSO 2 F - , a halide, OSO 2 CF 3 - , OSO 2 C 4 F 9 - , ##STR6## R is alkyl, aryl, aralkyl; and finally R 5 , R 6 , and R 7 substituent positions on the phenoxy ring are interchangeable, wherein the R 6 substituent of the polysubstituted aryl acridinium ester is covalently coupled to a molecule with biological activity which molecule is capable of being covalently coupled to the R 6 substituent.
Claim 3
Dependent Claim
62 words
A luminescent conjugate as recited in claim 1 wherein R 1 is a methyl group; R 2 , R 3 , R 5 and R 7 are hydrogen; R 4 and R 8 are a methyl group; R 10 is an N-succinimidyl oxycarbonyl group attached directly to the para-position of the phenoxy ring; and X is CH 3 SO 4 - .
Claim 4
Dependent Claim
20 words
A luminescent conjugate as recited in claim 1 wherein the molecule with biological activity is a molecule with immunological activity.
Claim 5
Dependent Claim
17 words
A luminescent conjugate as recited in claim 3 wherein the molecule with immunological activity is an antibody.
Claim 6
Dependent Claim
17 words
A luminescent conjugate as recited in claim 3 wherein the molecule with immunological activity is an antigen.
Claim 7
Dependent Claim
18 words
A luminescent conjugate as recited in claim 1 wherein the molecule with biological activity is a nucleic acid.
Claim 8
Dependent Claim
17 words
A luminescent conjugate as recited in claim 1 wherein the molecule with biological activity comprises nucleic acids.
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) | 1991-05-17 | 1991-11-16 | 1992-05-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-05-17 | 1995-11-16 | 1996-05-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-05-17 | 1999-11-16 | 2000-05-17 | $7700.00 | Window Closed / Lapsed |