Chemical synthesis of a novel aromatic amine mutagen isolated from water of the Nishitakase River in Kyoto and a possible route of its formation.
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.
Shiozawa
T
T
Graduate School of Nutritional and Environmental Sciences and School of Pharmaceutical Science, University of Shizuoka, 52-1, Yada, Shizuoka 422, Japan.
Muraoka
K
K
Nukaya
H
H
Ohe
T
T
Sawanishi
H
H
Oguri
A
A
Wakabayashi
K
K
Sugimura
T
T
Terao
Y
Y
D007564:Japan; D009153:Mutagens / Q000138:chemical synthesis*; D014230:Triazoles / Q000138:chemical synthesis*; D014874:Water Pollutants, Chemical / Q000138:chemical synthesis*
C112866:2-(2-(acetylamino)-4-(bis(2-methoxyethyl)amino)-5-methoxyphenyl)-5-amino-7-bromo-4-chloro-2H-benzotriazole; D009153:Mutagens; D014230:Triazoles; D014874:Water Pollutants, Chemical