Patent JPS5893592A successfully refreshed from Google Patents.
US5451683A
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Spatially-addressable immobilization of anti-ligands on surfaces
Assignee: Affymetrix Inc
•
Filing: 1993-04-23
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Granted: 1995-09-19
•
Expires: 2013-04-23
Abstract
Abstract Methods and compositions are described for immobilizing anti-ligands, such as antibodies or antigens, hormones or hormone receptors, oligonucleotides, and polysaccharides on surfaces of solid substrates for various uses. The methods provide surfaces covered with caged binding members which comprise protecting groups capable of being removed upon application of a suitable energy source. Spatially addressed irradiation of predefined regions on the surface permits immobilization of anti-ligands at the activated regions on the surface. Cycles of irradiation on different regions of the surface and immobilization of different anti-ligands allows formation of an immobilized matrix of anti-ligands at defined sites on the surface. The immobilized matrix of anti-ligands permits simultaneous screenings of a liquid sample for ligands having high affinities for certain anti-ligands of the matrix. A preferred embodiment of the invention involves attaching photoactivatable biotin derivatives to a surface. Photolytic activation of the biotin derivatives forms biotin analogs having strong binding affinity for avidin. Biotinylated anti-ligands can be immobilized on activated regions of the surface previously treated with avidin.
Inventors
- 👤 Ronald W. Barrett
- 👤 Michael C. Pirrung
- 👤 Lubert Stryer
- 👤 Christopher P. Holmes
- 👤 Steven A. Sundberg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 16:10
CPC Classifications
C; C07; C07D; C07D495/00; C07D495/02; C07D495/04; C07D233/00; C07D233/04; C07D233/28; C07D233/30; C07D233/32; C07D233/38; G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/53; G01N33/543; G01N33/54306; G01N33/54353; G01N33/551; G01N33/552; B; B01; B01J; B01J2219/00; B01J2219/00274; B01J2219/00583; B01J2219/00603; B01J2219/00605; B01J2219/00608; B01J2219/0061; B01J2219/00612; B01J2219/00614; B01J2219/00617; B01J2219/00623; B01J2219/00626; B01J2219/0063; B01J2219/00659; B01J2219/00718; B01J2219/0072; B01J2219/00722; C40; C40B; C40B40/00; C40B40/04; C40B40/06; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
302 words
A caged binding member compound having the formula: ##STR30## wherein X and Z are selected from the group consisting of (a) hydrogen, (b) oxycarbonyls of lower alkyl, aryl, and benzyl groups, (c) a nitroveratryloxycarbonyl group, (d) a nitropiperonyloxycarbonyl group where Z is hydrogen and R is p-nitrophenyl formate, (e) ##STR31## wherein R 1 and R 2 are hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, sulfonate, formamido or phosphido groups, (f) ##STR32## wherein R 1 and R 2 are hydrogen, lower alkyl, aryl, benzyl, pyrenyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido or phosphido groups, and R 3 and R 4 are hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido or phosphido groups, (g) ##STR33## wherein R 1 and R 2 are hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido or phosphido groups, and (h) ##STR34## wherein R 1 , R 2 , R 3 and R 4 are hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido or phosphido groups, provided that when X is hydrogen, Z is not hydrogen or methyloxycarbonyl and provided that when Z is hydrogen, X is not hydrogen or methyloxycarbonyl; R is selected from the group consisting of hydrogen, lower alkyl, aryl, carboxylate lower alkyl formate, aryl formate, methyl formate, p-nitrophenyl formate, formamide, N-alkylformamide, N-succinimidyl, hydroxyl, alkoxyl, thiol, thioether, disulfide, hydrazide and amine groups, provided that when X or Z is methyloxycarbonyl, R is not methyl formate; U is O, S or NH; Y is selected from the group consisting of sulfur, oxygen, methylene, carbonyl, sulfinyl and sulfonyl groups, or Y represents two hydrogens attached to the respective carbons; n=0-7; or acid addition salts of the compound.
Claim 2
Dependent Claim
302 words
A caged binding member compound having the formula: ##STR30## wherein X and Z are selected from the group consisting of (a) hydrogen, (b) oxycarbonyls of lower alkyl, aryl, and benzyl groups, (c) a nitroveratryloxycarbonyl group, (d) a nitropiperonyloxycarbonyl group where Z is hydrogen and R is p-nitrophenyl formate, (e) ##STR31## wherein R 1 and R 2 are hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, sulfonate, formamido or phosphido groups, (f) ##STR32## wherein R 1 and R 2 are hydrogen, lower alkyl, aryl, benzyl, pyrenyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido or phosphido groups, and R 3 and R 4 are hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido or phosphido groups, (g) ##STR33## wherein R 1 and R 2 are hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido or phosphido groups, and (h) ##STR34## wherein R 1 , R 2 , R 3 and R 4 are hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido or phosphido groups, provided that when X is hydrogen, Z is not hydrogen or methyloxycarbonyl and provided that when Z is hydrogen, X is not hydrogen or methyloxycarbonyl; R is selected from the group consisting of hydrogen, lower alkyl, aryl, carboxylate lower alkyl formate, aryl formate, methyl formate, p-nitrophenyl formate, formamide, N-alkylformamide, N-succinimidyl, hydroxyl, alkoxyl, thiol, thioether, disulfide, hydrazide and amine groups, provided that when X or Z is methyloxycarbonyl, R is not methyl formate; U is O, S or NH; Y is selected from the group consisting of sulfur, oxygen, methylene, carbonyl, sulfinyl and sulfonyl groups, or Y represents two hydrogens attached to the respective carbons; n=0-7; or acid addition salts of the compound.
Claim 3
Dependent Claim
15 words
A compound as in claim 1 wherein U is O, Y is sulfur, and n=4.
Claim 4
Dependent Claim
16 words
A compound as in claim 1 wherein one of X and Z is a nitroveratryloxycarbonyl group.
Claim 5
Dependent Claim
42 words
A compound as in claim 1 wherein one of X and Z has the formula: ##STR35## wherein R 1 and R 2 are hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, sulfonate, formamido or phosphido groups.
Claim 6
Dependent Claim
18 words
A compound as in claim 1 wherein X is 6-nitroveratryloxycarbonyl; Z is hydrogen; and R is methyl formate.
Claim 7
Dependent Claim
18 words
A compound as in claim 1 wherein X is 6-nitroveratryloxycarbonyl; Z is hydrogen; and R is p-nitrophenyl formate.
Claim 8
Dependent Claim
18 words
A compound as in claim 1 wherein X is 6-nitropiperonyloxycarbonyl, Z is hydrogen; and R is p-nitrophenyl formate.
Claim 9
Dependent Claim
65 words
A compound as in claim 1 wherein one of X and Z is ##STR36## wherein R 1 and R 2 are hydrogen, lower alkyl, aryl, benzyl, pyrenyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido or phosphido groups, and R 3 and R 4 are hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido or phosphido groups.
Claim 10
Dependent Claim
332 words
A caged binding member compound having the formula selected from the group consisting of: ##STR37## wherein X is selected from the group consisting of (a) hydrogen, (b) lower alkyl, (c) aryl, (d) benzyl, (e) substituted benzyl selected from the group consisting of ##STR38## wherein R 1 , R 2 , R 3 and R 4 are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido and phosphido groups provided that R 1 , R 2 , R 3 and R 4 are not all hydrogen, and ##STR39## wherein R 1 and R 2 are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido and phosphido groups. (f) nitroveratryl, (g) 6-nitroveratryl, (h) 6-nitroveratryloxycarbonyl, and (i) 6-nitropiperonyloxycarbonyl where U or W is hydrogen; U and W are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl and substituted benzyl selected from the group consisting of ##STR40## wherein R 1 , R 2 , R 3 and R 4 are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido and phosphido groups provided that R 1 , R 2 , R 3 and R 4 are not all hydrogen, and ##STR41## wherein R 1 and R 2 are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido and phosphido groups, provided that only one of U or W is present; R is selected from the group consisting of hydrogen, lower alkyl, aryl, carboxylate, alkyl formate, aryl formate, formamide, N-alkyl formamide, N-succinimidyl, hydroxyl, alkoxyl, thiol, thioether, disulfide, hydrazide and amine groups; Y is selected from the group consisting of sulfur, oxygen, methylene, carbonyl, sulfinyl and sulfonyl groups, or Y represents two hydrogens attached to the respective carbons; and n=0-7; or acid addition salts of the compound.
Claim 11
Dependent Claim
332 words
A caged binding member compound having the formula selected from the group consisting of: ##STR37## wherein X is selected from the group consisting of (a) hydrogen, (b) lower alkyl, (c) aryl, (d) benzyl, (e) substituted benzyl selected from the group consisting of ##STR38## wherein R 1 , R 2 , R 3 and R 4 are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido and phosphido groups provided that R 1 , R 2 , R 3 and R 4 are not all hydrogen, and ##STR39## wherein R 1 and R 2 are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido and phosphido groups. (f) nitroveratryl, (g) 6-nitroveratryl, (h) 6-nitroveratryloxycarbonyl, and (i) 6-nitropiperonyloxycarbonyl where U or W is hydrogen; U and W are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl and substituted benzyl selected from the group consisting of ##STR40## wherein R 1 , R 2 , R 3 and R 4 are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido and phosphido groups provided that R 1 , R 2 , R 3 and R 4 are not all hydrogen, and ##STR41## wherein R 1 and R 2 are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido and phosphido groups, provided that only one of U or W is present; R is selected from the group consisting of hydrogen, lower alkyl, aryl, carboxylate, alkyl formate, aryl formate, formamide, N-alkyl formamide, N-succinimidyl, hydroxyl, alkoxyl, thiol, thioether, disulfide, hydrazide and amine groups; Y is selected from the group consisting of sulfur, oxygen, methylene, carbonyl, sulfinyl and sulfonyl groups, or Y represents two hydrogens attached to the respective carbons; and n=0-7; or acid addition salts of the compound.
Claim 12
Dependent Claim
12 words
A compound as in claim 9 wherein Y is sulfur and n=4.
Claim 13
Dependent Claim
68 words
A compound as in claim 9 wherein one of X, U or W has the formula: ##STR42## wherein R 1 , R 2 , R 3 and R 4 are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido and phosphido groups provided that R 1 , R 2 , R 4 are not all hydrogen.
Claim 14
Dependent Claim
14 words
A compound as in claim 11 wherein R 1 and R 2 are methoxy.
Claim 15
Dependent Claim
14 words
A compound as in claim 11 wherein R 3 and R 4 are methyl.
Claim 16
Dependent Claim
12 words
A compound as in claim 9 wherein X is a nitroveratryl group.
Claim 17
Dependent Claim
43 words
A compound as in claim 9, wherein X has the formula: ##STR43## wherein R 1 and R 2 are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido and phosphido groups.
Claim 18
Dependent Claim
20 words
A compound as in claim 9 wherein X is 6-nitroveratryl; U or W is hydrogen: and R is methyl formate.
Claim 19
Dependent Claim
16 words
A compound as in claim 9 wherein X is 6-nitroveratryloxycarbonyl hydrogen; and R is p-nitrophenyl formate.
Claim 20
Dependent Claim
16 words
A compound as in claim 9 wherein X is 6-nitropiperonyloxycarbonyl and U or W is hydrogen.
Claim 21
Dependent Claim
21 words
A compound as in claim 9 wherein X is a substituted benzyl group, and R is methyl formate or p-nitrophenyl formate.
Claim 22
Dependent Claim
14 words
A compound as in claim 8 wherein R 1 and R 2 are methoxy.
Claim 23
Dependent Claim
14 words
A compound as in claim 8 wherein R 3 and R 4 are methyl.
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