Fast-flow EPR spectroscopic observation of the isoniazid, iproniazid, and phenylhydrazine hydrazyl radicals

Chem Res Toxicol. 2004 Feb;17(2):226-33. doi: 10.1021/tx0341759.

Abstract

Hydrazyl radical intermediates have been suggested as important intermediates in the biochemistry of hydrazides and hydrazines. Although spin-trapping studies have intercepted those species previously, there has been no report of the direct observation of the unstable hydrazyl radicals of isoniazid and iproniazid. We have employed the fast-flow technique in electron paramagnetic resonance (EPR) spectroscopy to measure spectra for the short-lived hydrazyl radicals of a family of hydrazides, including the pharmacologically important compounds isoniazid and iproniazid, as well as for a series of phenylhydrazines. Our investigations of the phenylhydrazine radical and the related chloro-substituted analogues have allowed definitive assignments of the hyperfine coupling constants of that toxicologically important free radical. Theoretical values of hyperfine coupling constants, calculated by density functional formalism, provided a guide to assignments for the hydrazyl species and confirmed the experimentally based assignments for phenylhydrazyl radical.

MeSH terms

  • Electron Spin Resonance Spectroscopy / methods*
  • Free Radicals
  • Iproniazid / analysis*
  • Isoniazid / analysis*
  • Phenylhydrazines / analysis*

Substances

  • Free Radicals
  • Phenylhydrazines
  • phenylhydrazine
  • Iproniazid
  • Isoniazid