2,4-Dinitrobiphenyl誘導体の変異原性代謝物質の構造について

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In order to elucidate the mechanisms of mutagenic activation of nitrobiphenyls in Salmonella typhimurium TA98 by use of a mammalian activation system, 2,4,6-trinitrobiphenyl (TNBp, 0.09 rev./nmol+S9) and 2,4,2', 4'-tetranitrobiphenyl (TNBp^*, 457.19 rev./nmol+S9) were incubated with 10% S9 mix, separately, and their mutagenic metabolites were separated by SiO_2 and Al_2O_3 column chromatography. In 2,4,6-TNBp, 4-amino-2,6-dinitroBp (0.11 rev./nmol-S9) and 2,4-diamino-6-nitroBp (0.50 rev./nmol-S9) were isolated from the reaction mixture of TNBp with S9 mix at 37℃ for 48 h, and their structures determined by their mass and ^1H-NMR spectra and the GC/MS data of their deamination products. In 2,4,2', 4'-TNBp^*, 2,4'-diamino-2', 4-dinitroBp (25460.01 rev./nmol-S9) and 2,2'-dinitrobenzidine (33.79 rev./nmol-S9) were isolated from the reaction mixture, and their structures also determined by their physico-chemical and the GC/MS data of their deamination products. From the high-performance liquid chromatographic analysis of these metabolites, the mutagenicity of 2,4'-diamino-2', 4-dinitroBp (-S9) contributed 100% of the mutagenicity of 2,4,2', 4'-TNBp^* (+S9), whereas the mutagenicity of 4-amino-2,6-dinitroBp and 2,4-diamino-6-nitroBp contributed only 0.8 and 0.4% of that of 2,4,6-TNBp (+S9), respectively. Mutagenicity of 2,2'-dinitrobenzidine was reduced to a half by the treatment with S9 mix, whereas the mutagenicity was expected to be enhanced by a mammalian metabolic activation system.
社団法人日本薬学会の論文
1991-06-30

2,4-Dinitrobiphenyl誘導体の変異原性代謝物質の構造について

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