Photoactivatable o-nitrobenzyl polyethylene glycol-silane for the production of patterned biomolecular arrays
First Claim
1. A compound having the formula:
- ##STR9## wherein R1 is --(CH2 CH2 O)n CH3, where n is an integer from about 6 to about 300, R2 is a linear linking group having a distal end that is capable of forming a covalent bond with a substrate, and R3 is NO2 or H.
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Abstract
O-nitrobenzyl analogs that include a photoremovable protecting group that resists the nonspecific adsorption of biomolecules and a linking group for attaching the o-nitrobenzyl analog to a substrate are disclosed. Also disclosed are methods for using o-nitrobenzyl analogs for creating patterned arrays of anti-ligands on a substrate so that a plurality of bioassays can be conducted simultaneously. In particular, the compounds disclosed are o-nitrobenzyl-polyethylene glycol-silanes, wherein the silane group serves to attach the compound to a substrate, the polyethylene glycol group resists the nonspecific adsorption of biomolecules. The o-nitrobenzyl group provides a photoactivatable functionality that allows the polyethylene glycol group to be selectively removed upon exposure to UV radiation and be replaced by an anti-ligand.
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Citations
21 Claims
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1. A compound having the formula:
- ##STR9## wherein R1 is --(CH2 CH2 O)n CH3, where n is an integer from about 6 to about 300, R2 is a linear linking group having a distal end that is capable of forming a covalent bond with a substrate, and R3 is NO2 or H.
- View Dependent Claims (2, 7, 8, 9, 10, 11, 12, 13)
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3. A compound having the formula:
- ##STR10## wherein R is a leaving group, m is an integer from about 9 to about 25, n is an integer from about 6 to about 300 and R3 is NO2 or H.
- View Dependent Claims (4)
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5. A modified substrate having a compound covalently bonded thereto, the compound having the formula:
- ##STR11## wherein R1 is --(CH2 CHO)n CH3, where n is an integer from about 6 to about 300, R2 is a linear linking group having a distal end that is covalently bonded to the solid substrate and R3 is NO2 or H.
- View Dependent Claims (6)
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14. A method for attaching a plurality of anti-ligands having different binding specificities to predefined regions on a substrate, the method comprising the steps of
(a) covalently binding to the substrate a protected o-nitrobenzyl analog of the formula: - ##STR15## wherein R is a leaving group, m is an integer from about 9 to about 25, and n is an integer from about 6 to about 300, and R3 is NO2 or H to form a modified substrate having bound thereto a compound of the formula;
##STR16## wherein Si forms at least one covalent bond with the substrate and x is an integer between 1 and 3 representing the number of covalent bonds between Si and the substrate, m is an integer from about 9 to about 25, and n is an integer from about 6 to about 300, and R3 is NO2 or H,(b) irradiating the protected o-nitrobenzyl analog on a first prefined region of the modified substrate to form unprotected o-nitrosobenzyl analog of the formula;
##STR17## wherein Si forms at least one covalent bond with the first predefined region of the modified substrate and x is an integer between 1 and 3 representing the number of covalent bonds between Si and the first predefined region of the modified substrate and m is an integer from about 9 to about 25 and R3 is NO2 or H,(c) reacting the unprotected o-nitrosobenzyl analog with an anti-ligand to covalently bind the anti-ligand to the unprotected o-nitrosobenzyl analog to form a bridging o-nitrosobenzyl analog of the formula;
##STR18## where Si forms at least one covalent bond with the first predefined region of the modified substrate and x is an integer between 1 and 3 representing the number of covalent bonds between Si and the first predefined region of the modified substrate, m is an integer from about 9 to about 25 and R3 is NO2 or H(d) washing the substrate to remove unbound anti-ligand, (e) repeating steps (b) to (d) at least one additional time on a different region of the modified substrate with a different anti-ligand. - View Dependent Claims (15, 16, 17, 18, 19)
- ##STR15## wherein R is a leaving group, m is an integer from about 9 to about 25, and n is an integer from about 6 to about 300, and R3 is NO2 or H to form a modified substrate having bound thereto a compound of the formula;
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20. A patterned substrate for performing a plurality of biological assays simultaneously, made by a process comprising the steps of:
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(a) covalently binding to the substrate a protected o-nitrobenzyl analog of the formula;
##STR19## wherein R is a leaving group, m is an integer from about 9 to about 25, and n is an integer from about 6 to about 300, and R3 is NO2 or H, to form a modified substrate having bound thereto a compound of the formula;
##STR20## wherein Si forms at least one covalent bond with the substrate and x is an integer between 1 and 3 representing the number of covalent bonds between Si and the substrate, m is an integer from about 9 to about 25, and n is an integer from about 6 to about 300, and R3 is NO2 or H,(b) irradiating the protected o-nitrobenzyl analog on a first predefined region of the substrate to form unprotected o-nitrosobenzyl analog of the formula;
##STR21## where Si forms at least one covalent bond with the first predefined region of the modified substrate and x is an integer between 1 and 3 representing the number of covalent bonds between Si and the first predefined region of the modified substrate and m is an integer from about 9 to about 25 and R3 is NO2 or H,(c) reacting the unprotected o-nitrosobenzyl analog with an anti-ligand to covalently bind the anti-ligand to the unprotected o-nitrosobenzyl analog to form a bridging o-nitrosobenzyl analog of the formula;
##STR22## where Si forms at least one covalent bond with the first predefined region of the modified substrate and x is an integer between 1 and 3 representing the number of covalent bonds between Si and the first predefined region of the modified substrate and m is an integer from about 9 to about 25 and R3 is NO2 or H,(d) washing the substrate to remove unbound anti-ligand, (e) repeating steps (b) to (d) at least one additional time on a different region of the modified substrate with a different anti-ligand. - View Dependent Claims (21)
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Specification