Studies on the Mutagenicity of o-Dinitrobenzene-nucleic Base Adducts in Salmonella typhimurium Strains and the Structural Elucidation of the Purine Adducts.

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  • ｏ‐Ｄｉｎｉｔｒｏｂｅｎｚｅｎｅ‐核酸塩基付加物のＳａｌｍｏｎｅｌｌａ　ｔｙｐｈｉｍｕｒｉｕｍ株に対する変異原性並びにプリン塩基付加物の構造について

Abstract

o-Dinitrobenzene (DNBz) and each nucleic base were made to react with NaOH in dimethylsulfoxide at room temperature for 3-60 h. All of the synthesized compounds were the 2-nitrophenyl adducts of nucleic bases. The mutagenicity test of the synthesized compounds and of o-DNBz were then carried out against Salmonella typhimurium TA98, TA98NR and TA100 without a mammalian metabolic activation system. o-DNBz has no mutagenic potency against all the strains at a dose up to 100 μg. In the compounds with the adducts of nucleic bases, the mutagenic potencies of the adducts of adenine and guanine in TA98 were 50 revertants/100 μg and 255 revertants/10 μg, respectively and the most potent mutagen in TA100 was an adduct of guanine (382 revertants/100μg). Finally, the structures of the adducts of adenine and guanine could be elucidated as N1-(2-nitrophenyl)-adenine and N1-(2-nitrophenyl)-guanine, respectively, by the acid and alkaline degradation and by the isopentyl nitrite treatment of these adducts.

Journal

  • Eisei kagaku

    Eisei kagaku 38 (4), 342-348, 1992

    The Pharmaceutical Society of Japan

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