Enzyme Induction and Comparative Oxidative Desulfuration of Isothiocyanates to Isocyanates

Chem Res Toxicol. Oct-Nov 1996;9(7):1072-8. doi: 10.1021/tx950213f.

Abstract

Enzyme induction of oxidative metabolism of isothiocyanates to isocyanates by rat liver microsomes and comparative metabolic conversion of some isothiocyanates were investigated. Metabolic activity was assayed by trapping the isocyanate metabolites from isothiocyanates with the inclusion of 2-aminofluorene to form the respective mixed ureas as previously described for the 2-naphthyl isothiocyanate. Male F344 rats were fed either a conventional grain diet for induction with Aroclor 1254 or AIN 76A diet without antioxidant beginning 2 weeks before treatment with Aroclor 1254, beta-naphthoflavone, isosafrole, or phenobarbital. Enzymes responsible for the metabolism of 1- and 2-naphthyl isothiocyanate were inducible by all four agents, Aroclor being the best under the current induction protocol and metabolic conversion assay procedure. On the other hand, enzymes responsible for the metabolism of benzyl isothiocyanate were induced only by Aroclor and, to a lesser extent, by phenobarbital. For the comparative metabolic conversion studies, using the microsomes from Aroclor-treated rats fed a conventional grain diet, the rates of metabolic conversion followed the order of 1-naphthyl > > phenyl > benzyl and phenethyl > > propyl, ethyl, and methyl isothiocyanates.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Aroclors / chemistry
  • Chlorodiphenyl (54% Chlorine)
  • Enzyme Induction
  • Isocyanates / metabolism*
  • Isothiocyanates / metabolism*
  • Male
  • Microsomes, Liver / enzymology
  • Microsomes, Liver / metabolism
  • Oxidoreductases / biosynthesis*
  • Rats
  • Rats, Inbred F344
  • Sulfur / metabolism*
  • Urea / chemistry

Substances

  • Aroclors
  • Isocyanates
  • Isothiocyanates
  • Chlorodiphenyl (54% Chlorine)
  • Sulfur
  • Urea
  • Oxidoreductases