US4794082A
Expired / Lapsed
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Biotinylating agents
Assignee: Siemens Healthcare Diagnostics GmbH Germany
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Filing: 1987-09-03
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Granted: 1988-12-27
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Expires: 2007-09-03
Abstract
Abstract Compounds having a dithiopyridyl moiety linked to a biotin moiety are useful as thiol specific biotinylating agents. The biotin label can be cleaved in a reducing environment to yield the native thiol.
Inventors
- 👤 Gerald F. Sigler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 03:24
CPC Classifications
C; C07; C07D; C07D495/00; C07D495/02; C07D495/04; Y; Y10; Y10S; Y10S435/00; Y10S435/8215; Y10S435/822; Y10S435/848; Y10S435/849
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
109 words
A method for preparing a biotin derivative of a thiol containing protein, said method comprising contacting said thiol containing protein in an aqueous buffered solution maintaining a pH in the range of 6 to 9 with a compound of the formula: ##STR9## where x and y are integers of 1 to 5, n is 0 or 1, R is --CONH or --CH(CO 2 H)NHCO-- and Z is a pyridyl group optionally substituted with one or more substituents of such type and in such position as to preserve the tautomerism of the thiol-thione generated upon cleavage of the --S--S-- group, in a water-miscible organic solvent, and isolating said biotin derivative.
Claim 2
Independent Claim
109 words
A method for preparing a biotin derivative of a thiol containing protein, said method comprising contacting said thiol containing protein in an aqueous buffered solution maintaining a pH in the range of 6 to 9 with a compound of the formula: ##STR9## where x and y are integers of 1 to 5, n is 0 or 1, R is --CONH or --CH(CO 2 H)NHCO-- and Z is a pyridyl group optionally substituted with one or more substituents of such type and in such position as to preserve the tautomerism of the thiol-thione generated upon cleavage of the --S--S-- group, in a water-miscible organic solvent, and isolating said biotin derivative.
Claim 3
Dependent Claim
18 words
A method according to claim 1 wherein the buffer is phosphate buffered saline maintaining a pH of 7.4.
Claim 4
Dependent Claim
16 words
A method according to claim 1 wherein the water-miscible organic solvent is a dioolar aprotic solvent.
Claim 5
Dependent Claim
13 words
The method according to claim 3 wherein the dipolar aprotic solvent is dimethylformamide.
Claim 6
Dependent Claim
11 words
A method according to claim 1 wherein an antioxidant is employed.
Claim 7
Dependent Claim
12 words
The method according to claim 5 wherein the antioxidant is ethylenediaminetetraacetic acid.
Claim 8
Dependent Claim
17 words
A method according to claim 1 wherein the thiol containing protein is a hormone, enzyme, or antibody.
Claim 9
Dependent Claim
14 words
A method according to claim 7 wherein the thiol containing substance is an enzyme.
Claim 10
Dependent Claim
13 words
The method according to claim 8 wherein the enzyme is Escherichia coli β-galactosidase.
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) | 1991-12-27 | 1992-06-27 | 1992-12-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-12-27 | 1996-06-27 | 1996-12-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-12-27 | 2000-06-27 | 2000-12-27 | $7700.00 | Window Closed / Lapsed |