Direct evidence that an arene oxide is a metabolic intermediate of 2,2′,5,5′-tetrachlorobiphenyl

S. Thomas Forgue, Bradley D. Preston, Walter A. Hargraves, Ieva L. Reich, James R. Allen

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

Radiolabeled arene oxide was recovered from incubations containing [3H]-2,2′,5,5′-tetrachlorobiphenyl (3H-TCB), unlabeled 2,2′,5,5′-tetrachlorobiphenyl-3,4-oxide (TCBAO), 3,3,3-trichloropropene-1,2-oxide (TCPO), NADPH, and liver microsomes from phenobarbital-induced rats. No labeled arene oxide was generated in the absence of NADPH, nor during the metabolism of unlabeled TCB in the presence of [3H]-H2O. The recovered oxide (radiolabeled and carrier) was characterized by mobility on silica gel and by conversion to 3- and 4-hydroxy-TCB. Formation of a dihydrodiol metabolite was apparently blocked by inhibition of epoxide hydrase. These data provide the first direct evidence that arene oxides are intermediates of halogenated biphenyl metabolism.

Original languageEnglish (US)
Pages (from-to)475-483
Number of pages9
JournalBiochemical and Biophysical Research Communications
Volume91
Issue number2
DOIs
StatePublished - Nov 28 1979
Externally publishedYes

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Molecular Biology
  • Cell Biology

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