The metabolic oxidation of the ethynyl group in 4-ethynylbiphenyl in vitro.
1. The metabolism of 4-ethynylbiphenyl has been studied in vitro with subcellular fractions of normal and induced rat liver, and rat intestinal microflora (caecal contents). 2. Oxidation was NADPH-dependent, was inhibited by CO and stimulated by pretreatment with phenobarbitone or 3-methylcholanthrene. 3. Oxidation of the ethynyl group occurred in washed microsomal preparations, but not significantly in soluble fractions. Oxidation of the ethynyl group by a microsomal fraction preceded aromatic hydroxylation and no metabolites containing the intact ethynyl group were detected. 4. The major metabolite in liver fractions was biphenyl-4-ylacetic acid. This was the only product produced by a modified Udenfriend system. 5. Metabolism of 4-ethynylbiphenyl by rat caecal contents under anaerobic conditions produced very small amounts of 4-vinylbiphenyl. 6. In a modified Ames test with Salmonella typhimurium TA98, 4-ethynylbiphenyl gave a weak positive result that was doubled after 'activation' with an induced rat S9 fraction.
D000114:Acetylene / Q000031:analogs & derivatives* / Q000378:metabolism; D000818:Animals; D001713:Biphenyl Compounds / Q000378:metabolism*; D002432:Cecum / Q000382:microbiology; D055598:Chemical Phenomena; D002621:Chemistry; D066298:In Vitro Techniques; D008099:Liver / Q000378:metabolism; D008297:Male; D009153:Mutagens; D010084:Oxidation-Reduction; D051381:Rats; D013347:Subcellular Fractions / Q000378:metabolism
D001713:Biphenyl Compounds; D009153:Mutagens; C023626:4-ethynylbiphenyl; D000114:Acetylene