Chemical Synthesis of a Novel Aromatic Amine Mutagen Isolated from Water of the Nishitakase River in Kyoto and a Possible Route of Its Formation

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• 作者：Tatsushi Shiozawa ; Koichi Muraoka ; Haruo Nukaya ; Takeshi Ohe ; Hiroyuki Sawanishi ; Atsuko Oguri ; Keiji Wakabayashi ; Takashi Sugimura ; and Yoshiyasu Terao
• 刊名：Chemical Research in Toxicology
• 出版年：1998
• 出版时间：April 1998
• 年：1998
• 卷：11
• 期：4
• 页码：375 - 380
• 全文大小：91K
• 年卷期：v.11,no.4(April 1998)
• ISSN：1520-5010

文摘

Among five mutagenic compounds isolated from water samples, takenat sites below thesewage plants of the Nishitakase River in Kyoto, Japan, the structureof compound I has beendetermined to be2-[2-(acetylamino)-4-[bis(2-methoxyethyl)amino]-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-1). Since thisnovel aromatic amine mutagen hascharacteristic substituents in its molecule, it is postulated that theazo dye, 2-[(2-bromo-4,6-dinitrophenyl)azo]-4-methoxy-5-[bis(2-methoxyethyl)amino]acetoanilide(AZO DYE-1), used asan industrial material, is converted to the corresponding2-phenylbenzotriazole derivative witha reducing reagent and subsequently to PBTA-1 by chlorination. Infact, AZO DYE-1 changedto the dechlorinated derivative of PBTA-1 (deClPBTA-1) on treatmentwith sodium hydrosulfite,and this reacted with sodium hypochlorite to produce PBTA-1.Moreover, the presence ofdeClPBTA-1 was confirmed in a river water sample, along with PBTA-1.PBTA-1 showedpotent mutagenic activities in Salmonella typhimurium TA98and YG1024, inducing 88 000and 3 000 000 revertants, respectively, per g, with S9 mix.deClPBTA-1 was also mutagenic,but less potent. From these observations, it is suggested thatPBTA-1 is produced from AZODYE-1 through deClPBTA-1, during industrial processes at dyeingfactories and the treatmentof wastewater at sewage plants.