Stable NO-delivering compounds
AssigneeDuke University
InventorsEric J. Toone, Jonathan S. 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.
Claims18
A compound containing at least one stabilized S-nitrosyl group and at least one free thiol group or free alcohol group, wherein the S-nitrosyl group is stabilized by the free alcohol group or the free thiol group and wherein the compound has a half-life for NO-release that is at least two times as great as the corresponding compound without the free thiol group or free alcohol group, wherein the compound is prepared by reacting a polythiol or a thioalcohol with a nitrosylating agent, with the proviso that the polythiol or thioalcohol is not a polypeptide, an unsubstituted straight chained or branched dithiolated alkane, an unsubstituted straight chained or branched thiolalkanol, 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 method of preparing a compound containing a stabilized S-nitrosyl group and a free thiol group or free alcohol group, wherein the S-nitrosyl group is stabilized by the free alcohol group or the free thiol group and wherein the compound has a half-life for NO-release that is at least two times as great as the corresponding compound without the free thiol group or free alcohol group, said method comprising the step of reacting a polythiol or a thioalcohol with a nitrosylating agent, with the proviso that the polythiol or thioalcohol is not a polypeptide, an unsubstituted straight chained or branched dithiolated alkane, an unsubstituted straight chained or branched thioalkanol, 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.