Isolation and Identification of a New 2-Phenylbenzotriazole-Type Mutagen (PBTA-3) in the Nikko River in Aichi, Japan
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- 作者：Tatsushi Shiozawa ; Atsuko Tada ; Haruo Nukaya ; Tetsushi Watanabe ; Yoshifumi Takahashi ; Masaharu Asanoma ; Takeshi Ohe ; Hiroyuki Sawanishi ; Taka Katsuhara ; Takashi Sugimura ; Keiji Wakabayashi ; and Yoshiy
- 刊名：Chemical Research in Toxicology
- 出版年：2000
- 出版时间：July 2000
- 年：2000
- 卷：13
- 期：7
- 页码：535 - 540
- 全文大小：137K
- 年卷期：v.13,no.7(July 2000)
- ISSN：1520-5010
文摘
We have previously determined the chemical structures of two 2-phenylbenzotriazolemutagens (PBTA-1 and PBTA-2) in blue cotton-adsorbed material from the Nishitakase Riverin Kyoto, Japan. In the present study, further analysis of mutagenic substances in the NikkoRiver, which flows through Aichi Prefecture in Japan, allowed the isolation of a new mutagen.Material (2.2 g) adsorbed on blue cotton (3 kg) at a site below the sewage plant on the NikkoRiver was purified by various column chromatographies, and a mutagen (120 
g) accountingfor 11% of the total mutagenicity was isolated. On the basis of data from UV, mass, and 1HNMR spectra of the mutagen, the compound was deduced to be a PBTA-1 analogue. As withPBTA-1, the mutagen was able to be synthesized from the azo dye 2-[(2-bromo-4,6-dinitrophenyl)azo]-4-methoxy-5-[(2-hydroxyethyl)amino]acetanilide by reduction and chlorination.Since all spectra of the mutagen isolated from the river water were the same as those of thesynthesized form, the structure was concluded to be 2-[2-(acetylamino)-4-[(2-hydroxyethyl)amino]-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-3). PBTA-3 is apotent mutagen, inducing 81 000 and 3 000 000 revertants per microgram of Salmonellatyphimurium TA 98 and YG1024 respectively, in the presence of an S9 mix. In addition to itsdetection in the water of the Nikko River, PBTA-3 was detected in water samples from threeother rivers flowing through regions where dyeing industries have been developed. Like PBTA-1and PBTA-2, PBTA-3 might have also been produced from azo dyes during industrial processesin dyeing factories and/or through treatment at sewage plants.
g) accountingfor 11% of the total mutagenicity was isolated. On the basis of data from UV, mass, and 1HNMR spectra of the mutagen, the compound was deduced to be a PBTA-1 analogue. As withPBTA-1, the mutagen was able to be synthesized from the azo dye 2-[(2-bromo-4,6-dinitrophenyl)azo]-4-methoxy-5-[(2-hydroxyethyl)amino]acetanilide by reduction and chlorination.Since all spectra of the mutagen isolated from the river water were the same as those of thesynthesized form, the structure was concluded to be 2-[2-(acetylamino)-4-[(2-hydroxyethyl)amino]-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-3). PBTA-3 is apotent mutagen, inducing 81 000 and 3 000 000 revertants per microgram of Salmonellatyphimurium TA 98 and YG1024 respectively, in the presence of an S9 mix. In addition to itsdetection in the water of the Nikko River, PBTA-3 was detected in water samples from threeother rivers flowing through regions where dyeing industries have been developed. Like PBTA-1and PBTA-2, PBTA-3 might have also been produced from azo dyes during industrial processesin dyeing factories and/or through treatment at sewage plants.