Oguri A, Shiozawa T, Terao Y, Nukaya H, Yamashita J, Ohe T, Sawanishi H, Katsuhara T, Sugimura T, Wakabayashi K
Cancer Prevention Division, National Cancer Center Research Institute, 1-1 Tsukiji 5-chome, Chuo-ku, Tokyo 104-0045, Japan.
Chem Res Toxicol. 1998 Oct;11(10):1195-200. doi: 10.1021/tx980133m.
We previously isolated five mutagens, compounds I-V, in blue rayon-adsorbed materials from the Nishitakase River in Kyoto. The chemical structure of compound I, a major mutagen that accounted for 21% of the total mutagenicity, was determined to be 2-[2-(acetylamino)-4-[bis(2-methoxyethyl)amino]-5-methoxyphenyl]-5-am ino-7-bromo-4-chloro-2H-benzotriazole (PBTA-1). Compound II was also a major mutagen and accounted for 17% of the total mutagenicity. In this study, a large quantity (1.2 mg) of compound II was isolated from adsorbate to 27 kg of blue cotton, and its UV, mass, and 1H NMR spectra were analyzed. On the basis of the spectral data, compound II was deduced to be the PBTA-1 analogue 2-[2-(acetylamino)-4-[N-(2-cyanoethyl)ethylamino]-5-methoxyphenyl]-5- amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-2). As with PBTA-1, PBTA-2 was synthesized from an azo dye by reduction and chlorination. Since all of the spectra of PBTA-2 coincided with those of compound II obtained from river water, compound II was concluded to be PBTA-2. PBTA-2 is a newly identified potent mutagen, which induces 93 000 and 3 200 000 revertants of Salmonella typhimurium TA98 and YG1024 per microgram, respectively, in the presence of S9 mix. Like PBTA-1, PBTA-2 may also be produced from an azo dye during industrial processes in dyeing factories and treatment at sewage plants.
我们之前从京都西高濑川的蓝色人造丝吸附材料中分离出了五种诱变剂，即化合物I - V。化合物I是一种主要的诱变剂，占总诱变性的21%，其化学结构被确定为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）。化合物II也是一种主要的诱变剂，占总诱变性的17%。在本研究中，从27千克蓝色棉的吸附物中分离出了大量（1.2毫克）的化合物II，并对其紫外光谱、质谱和1H核磁共振光谱进行了分析。根据光谱数据，推断化合物II为PBTA-1类似物2-[2-(乙酰氨基)-4-[N-(2-氰基乙基)乙氨基]-5-甲氧基苯基]-5-氨基-7-溴-4-氯-2H-苯并三唑（PBTA-2）。与PBTA-1一样，PBTA-
