Direct evidence that an arene oxide is a metabolic intermediate of 2,2',5,5'-tetrachlorobiphenyl. |
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| Authors: | S T Forgue B D Preston W A Hargraves I L Reich J R Allen |
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| Affiliation: | 1. Department of Pathology, Medical School, University of Wisconsin, Madison, WI 53706 USA;2. Experimental Pathology Unit, Wisconsin Regional Primate Research Center, University of Wisconsin, Madison, WI 53706 USA;3. Department of Chemistry, University of Wisconsin, Madison, WI 53706 USA |
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| 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. |
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| Keywords: | TCBAO 2,2′,5,5′-tetrachlorobiphenyl-3,4-oxide Br-AO 2,5-dibromo-2′,5′-dichlorobiphenyl-3,4-oxide TCPO 3,3,3-trichloropropene-1,2-oxide PCB Polychlorinated biphenyl GC gas chromatography GC-MS gas chromatography-mass spectroscopy INC#1 incubations as defined in text E-INC#1 material eluted from silica gel plates as defined in text |
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