Stable no-delivering compounds
AssigneeDuke University
InventorsEric Toone, Jonathan Stamler
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Abstract
Disclosed are novel NO-releasing compounds which comprise a stabilized S-nitrosyl group and a free alcohol or a free thiol group. Also disclosed is a method of preparing the NO-releasing compounds. The method comprises reacting a polythiol or a thioalcohol with a nitrosylating agent. Also disclosed are medical devices coated with the disclosed compounds, methods of delivering NO to treatments sites in a subject by utilizing the medical devices and methods of sterilizing surfaces.
Claims27
A compound containing at least one S-nitrosyl group and at least one free thiol group, and optionally one or more functional groups selected from the group consisting of alcohols, amides, thioamides, aldehydes, ketones, halogens, double bonds, triple bonds and aryl groups, wherein the compound has a molecular weight of at least 375 atomic mass units, wherein at least one free thiol is located within three covalent bonds of at least one S-nitrosyl group, or can be brought within about one to one and a half bond lengths of at least one S-nitrosyl group, with the proviso that the compound is not an S-nitrosylated derivative of a polypeptide, a polythiolated polysaccharide, or a polymer with pendant thiol groups and is not an S-nitrosylated derivative of a compound represented by one of the following structural formulas:
- wherein each Ra is —H or methyl and is independently chosen.
A method of preparing a compound containing at least one S-nitrosyl group and at least one free thiol group, and optionally containing one or more functional groups selected from the group consisting of alcohols, amides, thioamides, aldehydes, ketones, halogens, double bonds, triple bonds and aryl groups, wherein the compound has a molecular weight of at least 375 atomic mass units, wherein at least one free thiol is located within three covalent bonds of at least one S-nitrosyl group, or can be brought within about one to one and a half bond lengths of at least one S-nitrosyl group, said method comprising the step of reacting a polythiol or thioalcohol with a nitrosylating agent, with the proviso that the polythiol or thioalcohol is not a polypeptide, a polythiolated polysaccharide, or a polymer with pendant thiol groups and is not represented by one of the following structural formulas:
- wherein each Ra is —H or methyl and is independently chosen.
A compound containing at least one S-nitrosyl group and at least one free alcohol group, and optionally one or more functional groups selected from the group consisting of thiols, amides, thioamides, aldehydes, ketones, halogens, double bonds, triple bonds and aryl groups, wherein the compound has a molecular weight of at least 500 atomic mass units, and wherein at least one free alcohol group is located within three covalent bonds of at least one S-nitrosyl group, or can be brought within about one to one and a half bond lengths of at least one S-nitrosyl group, with the proviso that the compound is not an S-nitrosylated derivative of a polypeptide, a polythiolated polysaccharide, or a polymer with pendant thiol groups and is not an S-nitrosylated derivative of a compound represented by one of the following structural formulas:
- wherein each Ra is —H or methyl and is independently chosen.
A method of preparing a compound containing at least one S-nitrosyl group and at least one free alcohol group, and optionally containing one or more functional groups selected from the group consisting of thiols, amides, thioamides, aldehydes, ketones, halogens, double bonds, triple bonds and aryl groups, wherein the compound has a molecular weight of at least 500 atomic mass units, wherein at least one free alcohol group is located within three covalent bonds of at least one S-nitrosyl group, or can be brought within about one to one and a half bond lengths of at least one S-nitrosyl group, the method comprising the step of reacting a thioalcohol with a nitrosylating agent, with the proviso that the thioalcohol is not a polypeptide, a polythiolated polysaccharide, or a polymer with pendant thiol groups and is not represented by one of the following structural formulas:
- wherein each Ra is —H or methyl and is independently chosen.
Dependencies are inferred from the claim text.