Isolation and identification of a new 2-phenylbenzotriazole-type mutagen (PBTA-3) in the Nikko River in Aichi, Japan

Chemical Research in Toxicology

Volumn 13, Issue 7, 2000, Pages 535-540

  Shiozawa, Tatsushi ^a   Tada, Atsuko ^b   Nukaya, Haruo ^a   Watanabe, Tetsushi ^c   Takahashi, Yoshifumi ^c   Asanoma, Masaharu ^d   Ohe, Takeshi ^e   Sawanishi, Hiroyuki ^f   Katsuhara, Taka ^g   Sugimura, Takashi ^b   Wakabayashi, Keiji ^b   Terao, Yoshiyasu ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b NATIONAL CANCER CENTER RESEARCH INSTITUTE   (Japan)

^c KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^d NAGOYA CITY PUBLIC HEALTH RESEARCH INSTITUTE   (Japan)

^e KYOTO WOMEN'S UNIVERSITY   (Japan)

^f HOKURIKU UNIVERSITY   (Japan)

^g TSUMURA AND CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZO DYE; BENZOTRIAZOLE DERIVATIVE; MUTAGENIC AGENT;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHLORINATION; JAPAN; MUTAGEN TESTING; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; REVERTANT; RIVER; SEWAGE TREATMENT PLANT; SYNTHESIS; WATER POLLUTION;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; JAPAN; MAGNETIC RESONANCE SPECTROSCOPY; MUTAGENS; TRIAZOLES; WATER POLLUTANTS, CHEMICAL;

EID: 0033929570     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0000264     Document Type: Article

References (17)

1. International Agency for Research on Cancer (1991) Chlorinated drinking-water. In IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Vol. 52, pp 45-141, IARC, Lyon, France.
2. Holmbom, B. R., Voss, R. H., Mortimer, R. D., and Wong, A. (1981) Isolation and identification of an Ames-mutagenic compound present in kraft chlorination effluents. Tappi 64, 172-174.
3. Hemming, J., Holmbom, B., Reunanen, M., and Kronberg, L. (1986) Determination of the strong mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone in chlorinated drinking and humic waters. Chemosphere 15, 549-556.
4. Sayato, Y., Nakamuro, K., Ueno, H., and Goto, R. (1993) Identification of polycyclic aromatic hydrocarbons in mutagenic adsorbates to a copper-phthalocyanine derivative recovered from municipal river water. Mutat. Res. 300, 207-213.
5. Kreijl, C. F., and Slooff, W. (1985) Mutagenic activity in Dutch river water and its biological significance for fish. In Mutagenicity Testing in Environmental Pollution Control (Zimmermann, F. K., and Taylor-Mayer, R. E., Eds.) pp 86-104, Ellis Horwood, West Sussex. U.K.
6. Nukaya, H., Yamashita, J., Tsuji, K., Terao, Y., Ohe, T., Sawanishi, H., Katsuhara, T., Kiyokawa, K., Tezuka, M., Oguri, A., Sugimura, T., and Wakabayashi, K. (1997) Isolation and chemical-structural determination of a novel aromatic amine mutagen in water from the Nishitakase River in Kyoto. Chem. Res. Toxicol. 10, 1061-1066.
7. Kusamran, W. R., Wakabayashi, K., Oguri, A., Anong, T., Nagao, M., and Sugimura, T. (1994) Mutagenicities of Bangkok and Tokyo river waters. Mutat. Res. 32, 99-104.
8. Oguri, A., Shiozawa, T., Terac, T., Nukaya, H., Yamashita, J., Ohe, T., Sawanishi, H., Katsuhara, T., Sugimura, T., and Wakabayashi, K. (1998) Identification of a 2-phenylbenzotriazole (PBTA)-type mutagen, PBTA-2, in water from the Nishitakase River in Kyoto. Chem. Res. Toxicol. 11, 1195-1200.
9. Shiozawa, T., Muraoka, K., Nukaya, H., Ohe, T., Sawanishi, H., Oguri, A., Wakabayashi, K., Sugimura, T., and Terao, Y. (1998) Chemical synthesis of a novel aromatic amine mutagen isolated from water of the Nishitakase River in Kyoto, and possible route of its formation. Chem. Res. Toxicol. 11, 375-380.
10. Ohe, T., Takeuchi, N., Watanabe, T., Tada, A., Nukaya, H., Terao, Y., Sawanishi, H., Hirayama, T., Sugimura, T., and Wakabayashi, K. (1999) Quantification of two aromatic amine mutagens, PBTA-1 and PBTA-2, in the yodo river system. Environ. Health Perspect. 107, 701-704.
11. Shiozawa, T., Suyama, K., Nakano, K., Nukaya, H., Sawanishi, H., Oguri, A., Wakabayashi, K., and Terao, Y. (1999) Mutagenic activity of 2-phenylbenzotriazole derivatives related to a mutagen, PBTA-1, in river water. Mutat. Res. 442, 105-111.
12. Takahashi, M., Wakabayashi, K., Nagao, M., Yamamoto, M., Masui, T., Goto, T., Kinae, N., Tomita, I., and Sugimura, T. (1985) Quantification of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and 2-amino-3,8-dimethylimidazo[4,5-f]-quinoxaline (MeIQx) in beef extracts by liquid chromatography with electrochemical detection (LCEC). Carcinogenesis 6, 1195-1199.
13. Kira, S., Hayatsu, H., and Ogata, M. (1989) Detection of mutagenicity in mussels and their ambient water. Bull. Environ. Contam. Toxicol. 43, 583-589.
14. Hayatsu, H., Oka, T., Wakata, A., Ohara, Y., Hayatsu, T., Kobayashi, H., and Arimoto, S. (1983) Adsorption of mutagens to cotton bearing covalently bound trisulfo-copper-phthalocyanine. Mutat. Res. 119, 233-238.
15. Yahagi, T., Nagao, M., Seino, Y., Matsushima, T., Sugimura, T., and Okada, M. (1977) Mutagenicities of N-nitrosamines on Salmonella. Mutat. Res. 48, 121-130.
16. Watanabe, M., Ishidate, M., Jr., and Nohmi, T. (1990) Sensitive method for the detection of mutagenic nitroarenes and aromatic amines: new derivatives of Salmonella typhimurium tester strains possessing elevated O-acetyltransferase levels. Mutat. Res. 234, 337-348.
17. Dennis, W. H., Jr., Hull, L. A., and Rosenblatt, D. H. (1967) Oxidation of amines. IV. Oxidative fragmentation, J. Org. Chem. 32, 3783-3787.