Nitrate esters as nitric oxide donors: SS-nitrates

Org Lett. 2001 Apr 19;3(8):1113-6. doi: 10.1021/ol007022a.

Abstract

[structure: see text]. The important biological secondary messenger NO can be generated from exogenous nitrovasodilators and NO donors. Nitrate esters are nitrovasodilators and NO mimetics, believed to be biotransformed to NO in vivo. On the basis of a mechanistic hypothesis, nitrates have been synthesized that release NO at significant rates in neutral aqueous solution in the presence only of added thiol. The novel masked beta-mercaptonitrates reported (SS-nitrates), provide information on possible sulfhydryl-dependent biotransformation mechanisms for nitrates in clinical use.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Electrochemistry
  • Esters / chemistry*
  • Models, Chemical
  • Nitric Oxide / chemistry*
  • Sulfhydryl Compounds / chemistry

Substances

  • Esters
  • Sulfhydryl Compounds
  • Nitric Oxide