Mutagenesis, Vol. 17, No. 4, 293-299,
July 2002
© 2002 UK Environmental Mutagen Society/Oxford University Press
Mutagenicity of two 2-phenylbenzotriazole derivatives, 2-[2-(acetylamino)-4-(diethylamino)-5-methoxyphenyl]-5-amino- 7-bromo-4-chloro-2H-benzotriazole and 2-[2-(acetylamino)-4-(diallylamino)-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole and their detection in river water in Japan
Department of Public Health, Kyoto Pharmaceutical University, 5 Nakauchicho, Misasagi, Yamashina-ku, Kyoto 607-8414, Japan, 1 Graduate School of Nutritional and Environmental Sciences and 2 School of Pharmaceutical Science, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan, 3 Cancer Prevention Division, National Cancer Center Research Institute, 1-1 Tsukiji 5-chome, Chuo-ku, Tokyo 104-0045, Japan, 4 Faculty of Pharmaceutical Sciences, Hokuriku University, Kanagawa-machi, Kanazawa 920-1181, Japan and 5 Department of Food and Nutrition Science, Kyoto Women's University, Kitahiyoshi-cho, Imakumano, Higashiyama-ku, Kyoto 605-8501, Japan
We recently detected five 2-phenylbenzotriazole (PBTA)-type mutagens (PBTA-1, PBTA-2, PBTA-3, PBTA-4 and PBTA-6) in concentrates from several rivers that flow in geographically different areas in Japan containing textile-related industries. On the basis of synthesis studies, these five PBTA derivatives were deduced to have originated from the corresponding dinitrophenylazo dyes, which are industrial chemicals used in textile dyeing, via reduction and chlorination. 2-[(2-Bromo-4,6-dinitrophenyl)azo]-5-(diethylamino)-4-methoxyacetanilide (Color Index name Disperse Blue 291, CAS registry no. 56548-64-2) and 2-[(2-bromo-4,6-dinitrophenyl)azo]-5-(diallylamino)-4-methoxyacetanilide (Color Index name Disperse Blue 373, CAS registry no. 51868-46-3) are used in textile dyeing and have 2-[(2-bromo-4,6-dinitrophenyl)azo]-4-methoxyacetanilide moieties in their structures, which are thought to be essential for their conversion to mutagenic PBTA derivatives. In the present study we have synthesized 2-[2-(acetyl-amino)-4-(diethylamino)-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-7) and 2-[2-(acetylamino)-4-(diallylamino)-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-8) from Disperse Blue 291 and Disperse Blue 373, respectively, by reduction with iron powder and subsequent chlorination with sodium hypochlorite. Both PBTA-7 and PBTA-8 exerted strong mutagenicity in Salmonella typhimurium TA98 and YG1024 in the presence of S9 mix (43 000 and 1 430 000 revertants/nmol for PBTA-7 and 40 700 and 2 213 000 revertants/nmol for PBTA-8 in TA98 and YG1024). To clarify whether PBTA-7 and PBTA-8 exist in the environment, water samples were collected at seven sites in six rivers flowing through two different regions where textile dyeing industries are located. All water samples were mutagenic in Salmonella typhimurium YG1024 with S9 mix and their potencies ranged from 108 000 to 1 990 000 revertants/g blue rayon. PBTA-7 and PBTA-8 were detected in water samples from both regions at levels of <0.1–101.4 ng/g blue rayon and <0.1–48.9 ng/g blue rayon, respectively. In some samples PBTA-7 and PBTA-8 could contribute up to 15% of the water mutagenicity.
6 To whom correspondence should be addressed. Tel: +81 75 595 4650; Fax: +81 75 595 4769; Email: watanabe{at}mb.kyoto-phu.ac.jp