Structural determination of a directly mutagenic amino-nitrobiphenyl as the S9 metabolite of 2,4,2',4'-tetranitrobiphenyl in Salmonella typhimurium TA98. |
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Authors: | T Hirayama K Iguchi S Yoshida Y Yamanaka T Watanabe |
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Affiliation: | Department of Food Chemistry and Environmental Toxicology, Kyoto Pharmaceutical University, Japan. |
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Abstract: | In order to elucidate the mechanisms of mutagenic activation of nitrobiphenyls by mammalian activation systems, 2,4,2',4'-tetranitrobiphenyl was incubated with S9 and its mutagenic metabolites were separated by SiO2 and Al2O3 column chromatography. The most mutagenic diamino-dinitrobiphenyl was isolated from the reaction mixture of 2,4,2',4'-tetranitrobiphenyl with S9 mix at 37 degrees C for 48 h, and its mutability was 4646 revertants/50 ng in Salmonella typhimurium TA98 without S9 mix. The deamination product of this most mutagenic metabolite was identical to 2,4'-dinitrobiphenyl by gas chromatography-mass spectrometry. Therefore, the structure of the metabolite was determined as 2,4'-diamino-2',4-dinitrobiphenyl by its chemical and physico-chemical properties. |
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