Shiozawa T, Muraoka K, Nukaya H, Ohe T, Sawanishi H, Oguri A, Wakabayashi K, Sugimura T, Terao Y
Graduate School of Nutritional and Environmental Sciences and School of Pharmaceutical Science, University of Shizuoka, 52-1, Yada, Shizuoka 422, Japan.
Chem Res Toxicol. 1998 Apr;11(4):375-80. doi: 10.1021/tx970222j.
Among five mutagenic compounds isolated from water samples, taken at sites below the sewage plants of the Nishitakase River in Kyoto, Japan, the structure of compound I has been determined to be 2-[2-(acetylamino)-4-[bis(2-methoxyethyl)amino]-5-methoxyphenyl]-5-am ino-7-bromo-4-chloro-2H-benzotriazole (PBTA-1). Since this novel aromatic amine mutagen has characteristic substituents in its molecule, it is postulated that the azo dye, 2-[(2-bromo-4, 6-dinitrophenyl)azo]-4-methoxy-5-[bis(2-methoxyethyl)amino]acetoanili de (AZO DYE-1), used as an industrial material, is converted to the corresponding 2-phenylbenzotriazole derivative with a reducing reagent and subsequently to PBTA-1 by chlorination. In fact, AZO DYE-1 changed to the dechlorinated derivative of PBTA-1 (deClPBTA-1) on treatment with sodium hydrosulfite, and this reacted with sodium hypochlorite to produce PBTA-1. Moreover, the presence of deClPBTA-1 was confirmed in a river water sample, along with PBTA-1. PBTA-1 showed potent mutagenic activities in Salmonella typhimurium TA98 and YG1024, inducing 88 000 and 3 000 000 revertants, respectively, per microg, with S9 mix. deClPBTA-1 was also mutagenic, but less potent. From these observations, it is suggested that PBTA-1 is produced from AZO DYE-1 through deClPBTA-1, during industrial processes at dyeing factories and the treatment of wastewater at sewage plants.
从日本京都西高濑川污水处理厂下游采集的水样中分离出的5种诱变化合物中，化合物I的结构已确定为2-[2-(乙酰氨基)-4-[双(2-甲氧基乙基)氨基]-5-甲氧基苯基]-5-氨基-7-溴-4-氯-2H-苯并三唑（PBTA-1）。由于这种新型芳香胺诱变剂在其分子中具有特征性取代基，据推测用作工业原料的偶氮染料2-[(2-溴-4,6-二硝基苯基)偶氮]-4-甲氧基-5-[双(2-甲氧基乙基)氨基]乙酰苯胺（AZO DYE-1），用还原剂转化为相应的2-苯基苯并三唑衍生物，随后通过氯化转化为PBTA-1。事实上，AZO DYE-1在用连二亚硫酸钠处理时转变为PBTA-1的脱氯衍生物（deClPBTA-1），并且该衍生物与次氯酸钠反应生成PBTA-1。此外，在河水样本中证实了deClPBTA-1与PBTA-1同时存在。PBTA-1在鼠伤寒沙门氏菌TA98和YG1024中表现出强大的诱变活性，在有S9混合液存在的情况下，每微克分别诱导88000和3000000个回复突变体。deClPBTA-1也具有诱变作用，但活性较弱。从这些观察结果表明，在印染厂的工业过程和污水处理厂的废水处理过程中，PBTA-1是通过deClPBTA-1由AZO DYE-1产生的。
