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US4614723A
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Porphyrin derivatives as fluorescent markers for immunoassays
Assignee: F Hoffmann La Roche AG
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Filing: 1984-05-23
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Granted: 1986-09-30
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Expires: 2004-05-23
Abstract
Abstract There are described novel porphyrin derivatives of the general formula <IMAGE> I wherein either R1 signifies the group <IMAGE> and R2 signifies the group <IMAGE> +TR <IMAGE> or R1 signifies the group <IMAGE> and R2 signifies the group <IMAGE> whereby X- signifies a halogen ion, an arylsulphonate ion, an alkylsulphonate ion or an alkyl sulphate ion, A signifies (C1-8)-alkylene and R3 signifies (C1-4)-alkyl, and sulphonic acid salts of compounds of formula I in which R1 signifies the group <IMAGE> as well as a process for their manufacture and intermediates used in this process. Because of their water-solubility the novel porphyrin derivatives are suitable as label molecules for highly sensitive fluorescence immuno-assays, especially for time-resolving fluorescence immuno-assays. The coupling of the novel porphyrin derivatives to immunologically-active materials is carried out in the customary manner, for example with a water-soluble carbodiimide derivative.
Inventors
- 👤 Dieter Schmidt
- 👤 Hans Steffen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 09:18
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/22; G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/53; G01N33/531; G01N33/532; G01N33/533; Y; Y10; Y10S; Y10S436/00; Y10S436/80
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
35 words
A porphyrin compound of the formula: ##STR22## wherein R 1 is ##STR23## R 2 is ##STR24## A is (C 1-8 )-alkylene, and the salts thereof, wherein said salts are formed from inorganic or organic bases.
Claim 2
Dependent Claim
35 words
A porphyrin compound of the formula: ##STR22## wherein R 1 is ##STR23## R 2 is ##STR24## A is (C 1-8 )-alkylene, and the salts thereof, wherein said salts are formed from inorganic or organic bases.
Claim 3
Dependent Claim
10 words
A compound according to claim 1 which is 4-[10,15,20-tris(4-sulphophenyl)-21H,23H-porphin-5-yl]-benzoic acid.
Claim 4
Dependent Claim
10 words
A compound according to claim 1 which is [4-[10,15,20-tris(4-sulphophenyl)-21H-23H-porphin-5-yl]phenoxy]acetic acid.
Claim 5
Dependent Claim
10 words
A compound according to claim 1 which is 6-[4-[10,15,20-tris(4-sulphophenyl)-21H,23H-porphin-5-yl]phenyl]hexanecarboxylic acid.
Claim 6
Dependent Claim
10 words
A compound according to claim 1 which is 1-(carboxymethyl)-1',1",1"'-trimethyl-4,4',4",4"'-(21H,23H-porphin-5,10,15,20-tetrayl)tetrakispyridinium tetraiodide.
Claim 7
Dependent Claim
25 words
Compounds of the formula ##STR25## wherein R 4 is selected from the group consisting of --COOH, --A--COOH and --O--A--COOH and A is (C 1-8 )-alkylene.
Claim 8
Dependent Claim
25 words
Compounds of the formula ##STR25## wherein R 4 is selected from the group consisting of --COOH, --A--COOH and --O--A--COOH and A is (C 1-8 )-alkylene.
Claim 9
Dependent Claim
37 words
Compounds of the formula ##STR26## wherein X - is selected from the group consisting of halogen ions, benzenesulfonate ions, p-toluenesulfonate ions, (C 1-12 )-alkylsulfonate ions and (C 1-12 )-alkyl sulphate ions and A is (C 1-8 )-alkylene.
Claim 10
Dependent Claim
37 words
Compounds of the formula ##STR26## wherein X - is selected from the group consisting of halogen ions, benzenesulfonate ions, p-toluenesulfonate ions, (C 1-12 )-alkylsulfonate ions and (C 1-12 )-alkyl sulphate ions and A is (C 1-8 )-alkylene.
Claim 11
Dependent Claim
59 words
A fluorescent antibody, consisting essentially of an antibody specific to an antigen to be detected, and, conjugated to said antibody, a fluorescent compound of the formula ##STR27## wherein R 1 is ##STR28## and R 2 is ##STR29## A is (C 1-8 )-alkylene and the salts of said fluorescent compound, wherein said salts are formed from inorganic or organic bases.
Claim 12
Dependent Claim
59 words
A fluorescent antibody, consisting essentially of an antibody specific to an antigen to be detected, and, conjugated to said antibody, a fluorescent compound of the formula ##STR27## wherein R 1 is ##STR28## and R 2 is ##STR29## A is (C 1-8 )-alkylene and the salts of said fluorescent compound, wherein said salts are formed from inorganic or organic bases.
Claim 13
Dependent Claim
15 words
A fluorescent antibody according to claim 8 wherein the antibody is specific to carcinoembryonal antigen.
Claim 14
Dependent Claim
19 words
A fluorescent antibody according to claim 9 wherein a water-soluble carbodiimide derivative couples the antibody to said fluorescent compound.
Claim 15
Dependent Claim
59 words
In an immunoassay of the time resolving type which utilizes an antibody conjugated to fluorescent label, the improvement which comprises using as said label a compound of the formula ##STR30## wherein R 1 is ##STR31## and R 2 is ##STR32## A is (C 1-8 )-alkylene and the salts thereof wherein said salts are formed from inorganic or organic bases.
Claim 16
Dependent Claim
59 words
In an immunoassay of the time resolving type which utilizes an antibody conjugated to fluorescent label, the improvement which comprises using as said label a compound of the formula ##STR30## wherein R 1 is ##STR31## and R 2 is ##STR32## A is (C 1-8 )-alkylene and the salts thereof wherein said salts are formed from inorganic or organic bases.
Claim 17
Dependent Claim
54 words
A porphyrin compound of the formula: ##STR33## wherein R 1 is ##STR34## R 2 is ##STR35## X - is selected from the group consisting of halogen ions, benzene sulfonate ions, p-toluenesulfonate ions, (C 1-12 )-alkylsulfonate ions and (C 1-12 )-alkyl sulphate ions; A is (C 1-8 )-alkylene; and R 3 is (C 1-4 )-alkyl.
Claim 18
Dependent Claim
54 words
A porphyrin compound of the formula: ##STR33## wherein R 1 is ##STR34## R 2 is ##STR35## X - is selected from the group consisting of halogen ions, benzene sulfonate ions, p-toluenesulfonate ions, (C 1-12 )-alkylsulfonate ions and (C 1-12 )-alkyl sulphate ions; A is (C 1-8 )-alkylene; and R 3 is (C 1-4 )-alkyl.
Claim 19
Dependent Claim
16 words
A compound according to claim 12 wherein R 1 is ##STR36## and R 2 is ##STR37##
Claim 20
Dependent Claim
11 words
A compound according to claim 12 wherein R 2 is ##STR38##
Claim 21
Dependent Claim
16 words
A compound according to claim 1 wherein said salts are alkali metal salts or ammonium salts.
Claim 22
Dependent Claim
13 words
A compound according to claim 15 wherein said salt is the sodium salt.
Claim 23
Dependent Claim
12 words
A compound according to claim 12 wherein X - is p-toluenesulfonate ion.
Claim 24
Dependent Claim
12 words
A compound according to claim 12 wherein X - is halogen ion.
Claim 25
Dependent Claim
14 words
A fluorescent antibody according to claim 10 wherein said carbodiimide derivative is 1-cyclohexyl-3-(2-morpholinoethyl)-carbodiimide methyl-p-toluenesulfonate.
Claim 26
Dependent Claim
68 words
A fluorescent antibody consisting essentially of, an antibody specific to an antigen to be detected, and, conjugated to said antibody, a fluorescent compound of the formula ##STR39## wherein R 1 is ##STR40## R 2 is ##STR41## X - is selected from the group consisting of halogen ions, benzene sulfonate ions, p-toluenesulfonate ions, (C 1-12 )-alkylsulfonate ions and (C 1-12 )-alkyl sulphate ions; R 3 is (C 1-4 )-alkyl.
Claim 27
Dependent Claim
68 words
A fluorescent antibody consisting essentially of, an antibody specific to an antigen to be detected, and, conjugated to said antibody, a fluorescent compound of the formula ##STR39## wherein R 1 is ##STR40## R 2 is ##STR41## X - is selected from the group consisting of halogen ions, benzene sulfonate ions, p-toluenesulfonate ions, (C 1-12 )-alkylsulfonate ions and (C 1-12 )-alkyl sulphate ions; R 3 is (C 1-4 )-alkyl.
Claim 28
Dependent Claim
15 words
A fluorescent antibody according to claim 20 wherein the antibody is specific to carcinoembryonal antigen.
Claim 29
Dependent Claim
19 words
A fluorescent antibody according to claim 21 wherein a water-soluble carbodiimide derivative couples said antibody to said fluorescent compound.
Claim 30
Dependent Claim
14 words
A fluorescent antibody according to claim 22 wherein said carbodiimide derivative is 1-cyclohexyl-3-(2-morpholinoethyl)-carbodiimide methyl-p-toluenesulfonate.
Claim 31
Dependent Claim
71 words
In an immunoassay of the time resolving type which utilizes an antibody conjugated to fluorescent label, the improvement which comprises using as said label a compound of the formula: ##STR42## wherein R 1 is ##STR43## R 2 is ##STR44## X - is selected from the group consisting of halogen ions, benzene sulfonate ions, p-toluenesulfonate ions, (C 1-12 )-alkylsulfonate ions and (C 1-12 )-alkyl sulphate ions; R 3 is (C 1-4 )-alkyl.
Claim 32
Dependent Claim
71 words
In an immunoassay of the time resolving type which utilizes an antibody conjugated to fluorescent label, the improvement which comprises using as said label a compound of the formula: ##STR42## wherein R 1 is ##STR43## R 2 is ##STR44## X - is selected from the group consisting of halogen ions, benzene sulfonate ions, p-toluenesulfonate ions, (C 1-12 )-alkylsulfonate ions and (C 1-12 )-alkyl sulphate ions; R 3 is (C 1-4 )-alkyl.
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) | 1989-09-29 | 1990-03-31 | 1990-09-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-09-29 | 1994-03-31 | 1994-09-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-09-29 | 1998-03-31 | 1998-09-30 | $7700.00 | Window Closed / Lapsed |