Inhibition of peroxynitrite-induced nitration of tyrosine by glutathione in the presence of carbon dioxide through both radical repair and peroxynitrate formation

Chemistry. 2001 Aug 3;7(15):3313-20. doi: 10.1002/1521-3765(20010803)7:15<3313::aid-chem3313>3.0.co;2-7.

Abstract

Peroxynitrite (ONOO-/ONOOH) is assumed to react preferentially with carbon dioxide in vivo to produce nitrogen dioxide (NO2*) and trioxocarbonate(1-) (CO3*-) radicals. We have studied the mechanism by which glutathione (GSH) inhibits the NO2*/CO3*--mediated formation of 3-nitrotyrosine. We found that even low concentrations of GSH strongly inhibit peroxynitrite-dependent tyrosine consumption (IC50 = 660 microM) as well as 3-nitrotyrosine formation (IC50) = 265 microM). From the determination of the level of oxygen produced or consumed under various initial conditions, it is inferred that GSH inhibits peroxynitrite-induced tyrosine consumption by re-reducing (repairing) the intermediate tyrosyl radicals. An additional protective pathway is mediated by the glutathiyl radical (GS*) through reduction of dioxygen to superoxide (O2*-) and reaction with NO2* to form peroxynitrate (O2NOOH/O2NOO-), which is largely unreactive towards tyrosine. Thus, GSH is highly effective in protecting tyrosine against an attack by peroxynitrite in the presence of CO2. Consequently, formation of 3-nitrotyrosine by freely diffusing NO2* radicals is highly unlikely at physiological levels of GSH.

MeSH terms

  • Antioxidants / chemistry
  • Carbon Dioxide / chemistry
  • Free Radicals / chemistry
  • Glutathione / chemistry*
  • Glutathione / pharmacology
  • Peroxynitrous Acid / chemistry*
  • Superoxides / chemistry*
  • Tyrosine / analogs & derivatives*
  • Tyrosine / antagonists & inhibitors
  • Tyrosine / chemistry*

Substances

  • Antioxidants
  • Free Radicals
  • Superoxides
  • Carbon Dioxide
  • Peroxynitrous Acid
  • 3-nitrotyrosine
  • Tyrosine
  • Glutathione