One-electron reduction of S-nitrosothiols in aqueous medium

Free Radic Biol Med. 2006 Oct 15;41(8):1240-6. doi: 10.1016/j.freeradbiomed.2006.06.025. Epub 2006 Jul 11.

Abstract

One-electron reduction of S-nitrosothiols (RSNO) has been studied using radiolytically produced reducing entity, the hydrated electron (e(aq)(-)), in aqueous medium. Both kinetics of the reaction and the mechanistic aspects of the decomposition of S-nitroso derivatives of glutathione, L-cysteine, N-acetyl-L-cysteine, N-acetyl-D,L-penicillamine, N-acetylcysteamine, L-cysteine methyl ester, and D,L-penicillamine have been investigated at neutral and acidic pH. The second-order rate constants of the reaction of e(aq)(-) with RSNOs were determined using a pulse radiolysis technique and were found to be diffusion controlled (10(10) dm(3) mol(-1) s(-1)) at neutral pH. The product analysis using HPLC, fluorimetry, and MS revealed the formation of thiol and nitric oxide as the major end products. It is therefore proposed that one-electron reduction of RSNO leads to the liberation of NO. There is no intermediacy of a thiyl radical as in the case of oxidation reactions of RSNOs. The radical anion of RSNO (RSN(*)O(-)) is proposed as a possible intermediate. The overall reaction could be written as RSNO + e(aq)(-) --H+--> RSH + (*)NO.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Electrons
  • Free Radicals / chemistry
  • Free Radicals / metabolism
  • In Vitro Techniques
  • Kinetics
  • Nitric Oxide / metabolism
  • Oxidation-Reduction
  • S-Nitrosothiols / chemistry
  • S-Nitrosothiols / metabolism*
  • Water

Substances

  • Free Radicals
  • S-Nitrosothiols
  • Water
  • Nitric Oxide