Mutagenic activity of 2-phenylbenzotriazole derivatives related to a mutagen, PBTA-1, in river water.
A mutagen, 2-[2-(acetylamino)-4-[bis(2-methoxyethyl)amino]-5-methoxyphenyl]5-ami no-7-bromo-4-chloro-2H-benzotriiazole (PBTA-1), isolated from water of the Nishitakase River in Kyoto exhibits potent mutagenic activity in Salmonella typhimurium TA98 with S9 mix and has characteristic moieties, including bromo, chloro, acetylamino, bis(2-methoxyethyl)amino and primary amino groups on a 2-phenylbenzotriazole skeleton. The mutagenicities of PBTA-1, its congeners and five related 2-phenylbenzotriazoles were examined in S. typhimurium TA98 with S9 mix in order to elucidate the structure-activity relationships. The data obtained suggest that a primary amino group plays an essential role in the mutagenic activity as do aromatic amines including heterocyclic amines in cooked foods. The effect of planarity of the 2-phenylbenzotriazole ring was significant, and in addition, halogen groups of PBTA-1 influenced the enhancement of the mutagenic activity.
Shiozawa
T
T
Institute for Environmental Sciences, University of Shizuoka, 52-1 Yada, 422-8526, Shizuoka, Japan.
Suyama
K
K
Nakano
K
K
Nukaya
H
H
Sawanishi
H
H
Oguri
A
A
Wakabayashi
K
K
Terao
Y
Y
D000818:Animals; D008297:Male; D008862:Microsomes, Liver / Q000187:drug effects; D009152:Mutagenicity Tests; D009153:Mutagens / Q000737:chemistry / Q000633:toxicity*; D051381:Rats; D017207:Rats, Sprague-Dawley; D012486:Salmonella typhimurium / Q000187:drug effects / Q000235:genetics; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000737:chemistry / Q000633:toxicity*; D014874:Water Pollutants, Chemical / Q000633:toxicity*
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