Hirayama T, Kusakabe H, Watanabe T, Ono M, Fukui S
Mutat Res. 1987 Jun;191(2):73-8. doi: 10.1016/0165-7992(87)90132-1.
3,4-Dinitrobiphenyl derivatives were mutagenic in Salmonella typhimurium TA98, TA98/1,8-DNP6 and in TA98NR. We describe here the specific reactivity of 3,4-dinitrobiphenyl derivatives with diluted sodium hydroxide solution and the determination of the amounts of released nitrous ion. 3,4-Dinitrobiphenyl derivatives begin to release nitrous ions when treated with NaOH solution at a concentration of 10(-3) N. The behavior of 4NQO and o-dinitrobenzene was the same as that of 3,4-dinitrobiphenyl derivatives. The residues of 3,4-dinitrobiphenyl derivatives, after releasing nitrous ions, were estimated to be hydroxy-nitrobiphenyls, as by GC/MS, we found the formation of o-nitrophenol in the reaction mixture of o-dinitrobenzene with aqueous NaOH solution. 3,4,4'-Trinitrobiphenyl, 3,4,3',4'-tetranitrobiphenyl and 4NQO had reduced mutagenic potency in Salmonella typhimurium TA98 following treatment with diluted NaOH. In order to elucidate the ultimate forms of 3,4-dinitrobiphenyl derivatives, we investigated the reaction of o-dinitrobenzene as a basic model substance of 3,4-dinitrobiphenyl, with nucleic bases in the presence of NaOH in nonaqueous solvent. o-Nitrophenyl guanine and adenine adducts were obtained.
3,4-二硝基联苯衍生物在鼠伤寒沙门氏菌TA98、TA98/1,8-DNP6和TA98NR中具有致突变性。我们在此描述3,4-二硝基联苯衍生物与稀氢氧化钠溶液的特定反应性以及所释放亚硝酸根离子量的测定。当用浓度为10(-3)N的氢氧化钠溶液处理时，3,4-二硝基联苯衍生物开始释放亚硝酸根离子。4-硝基喹啉-N-氧化物（4NQO）和邻二硝基苯的行为与3,4-二硝基联苯衍生物相同。在释放亚硝酸根离子后，3,4-二硝基联苯衍生物的残留物据估计为羟基硝基联苯，因为通过气相色谱/质谱法（GC/MS），我们在邻二硝基苯与氢氧化钠水溶液的反应混合物中发现了邻硝基苯酚的形成。在用稀氢氧化钠处理后，3,4,4'-三硝基联苯、3,4,3',4'-四硝基联苯和4NQO在鼠伤寒沙门氏菌TA98中的致突变性降低。为了阐明3,4-二硝基联苯衍生物的最终形式，我们研究了作为3,4-二硝基联苯基本模型物质的邻二硝基苯在非水溶剂中于氢氧化钠存在下与核酸碱基的反应。得到了邻硝基苯基鸟嘌呤和腺嘌呤加合物。
