Esters of 5-carboxyl-5-methyl-1-pyrroline N-oxide: a family of spin traps for superoxide

J Org Chem. 2003 Oct 3;68(20):7811-7. doi: 10.1021/jo0350413.

Abstract

Apparent rate constants, at acidic pH and neutral pH for the reaction of a family of ester-containing 5-carboxyl-5-methyl-1-pyrroline N-oxides with superoxide (O2*-) were estimated, using ferricytochrome c as a competitive inhibitor. It was of interest to note that the rate constants were similar among the different nitrones and not that significantly different from that found for 5-(diethoxyphosphoryl)-5-dimethyl-1-pyrroline N-oxide. At acidic pH, the rate constant for spin trapping O2*- was 3-fold greater than that at physiological pH. Subsequent experiments determined the half-life of aminoxyls, derived from the reaction of these nitrones with O2*-. The EPR spectra were modeled by using a global analysis method. The results clearly demonstrated that EPR spectra of all the aminoxyls were inconsistent with a model that included a single gamma-hydrogen splitting. A better interpretation modeled them as two diastereomers with identical nitrogen splittings and slightly different beta-hydrogen splittings. Detailed line width analyses slightly favored an equal line width-unequal population ratio for the two diastereomers.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Binding, Competitive
  • Cyclic N-Oxides / chemistry*
  • Cytochromes c / chemistry
  • Electron Spin Resonance Spectroscopy / methods
  • Esters / chemistry*
  • Half-Life
  • Hydrogen-Ion Concentration
  • Kinetics
  • Pyrroles / chemistry*
  • Spin Labels*
  • Spin Trapping
  • Superoxides / analysis
  • Superoxides / chemistry*
  • Xanthine / chemistry
  • Xanthine Oxidase / chemistry

Substances

  • Cyclic N-Oxides
  • Esters
  • Pyrroles
  • Spin Labels
  • Superoxides
  • Xanthine
  • pyrroline
  • Cytochromes c
  • Xanthine Oxidase