Superoxide modulates the oxidation and nitrosation of thiols by nitric oxide-derived reactive intermediates. Chemical aspects involved in the balance between oxidative and nitrosative stress

J Biol Chem. 1997 Apr 25;272(17):11147-51. doi: 10.1074/jbc.272.17.11147.

Abstract

Thiol-containing proteins are key to numerous cellular processes, and their functions can be modified by thiol nitrosation or oxidation. Nitrosation reactions are quenched by O-2, while the oxidation chemistry mediated by peroxynitrite is quenched by excess flux of either NO or O-2. A solution of glutathione (GSH), a model thiol-containing tripeptide, exclusively yielded S-nitrosoglutathione when exposed to the NO donor, Et2NN(O)NONa. However, when xanthine oxidase was added to the same mixture, the yield of S-nitrosoglutathione dramatically decreased as the activity of xanthine oxidase increased, such that there was a 95% reduction in nitrosation when the fluxes of NO and O-2 were nearly equivalent. The presence of superoxide dismutase reversed O-2-mediated inhibition, while catalase had no effect. Increasing the flux of O-2 yielded oxidized glutathione (GSSG), peaking when the flux of NO and O-2 were approximately equivalent. The results suggest that oxidation and nitrosation of thiols by superoxide and NO are determined by their relative fluxes and may have physiological significance.

MeSH terms

  • Free Radicals
  • Glutathione / analogs & derivatives
  • Glutathione / analysis
  • Glutathione / chemistry*
  • Glutathione / metabolism
  • Glutathione Disulfide
  • Hydrazines
  • Models, Chemical
  • Nitrates / chemistry
  • Nitric Oxide / chemistry*
  • Nitrogen Oxides
  • Nitroso Compounds
  • Oxidation-Reduction
  • S-Nitrosoglutathione
  • Sulfhydryl Compounds / chemistry*
  • Superoxides / chemistry*
  • Triazoles
  • Xanthine Oxidase / metabolism

Substances

  • Free Radicals
  • Hydrazines
  • Nitrates
  • Nitrogen Oxides
  • Nitroso Compounds
  • Sulfhydryl Compounds
  • Triazoles
  • Superoxides
  • peroxynitric acid
  • Nitric Oxide
  • S-Nitrosoglutathione
  • 1,1-diethyl-2-hydroxy-2-nitrosohydrazine
  • Xanthine Oxidase
  • Glutathione
  • Glutathione Disulfide