Detection of a novel mutagen, 3,6-dinitrobenzo[e]pyrene, as a major contaminant in surface soil in Osaka and Aichi Prefectures, Japan

Chemical Research in Toxicology

Volumn 18, Issue 2, 2005, Pages 283-289

  Watanabe, Tetsushi ^a   Hasei, Tomohiro ^a   Takahashi, Tomoyuki ^a   Asanoma, Masaharu ^b   Murahashi, Tsuyoshi ^a   Hirayama, Teruhisa ^a   Wakabayashi, Keiji ^c  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^b NAGOYA CITY PUBLIC HEALTH RESEARCH INSTITUTE   (Japan)

^c NATIONAL CANCER CENTER RESEARCH INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DINITROPYRENE; 1,6 DINITROPYRENE; 1,8 DINITROPYRENE; 3,6 DINITROBENZO[E]PYRENE; BENZO[E]PYRENE; MUTAGENIC AGENT; POLYCYCLIC AROMATIC HYDROCARBON; PYRENE DERIVATIVE; UNCLASSIFIED DRUG;

AMES TEST; ARTICLE; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; EXTRACTION; GEOGRAPHY; JAPAN; MASS SPECTROMETRY; MOLECULAR WEIGHT; MUTAGENICITY; NITRATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; REVERTANT; SALMONELLA TYPHIMURIUM; SOIL POLLUTION; SURFACE SOIL;

BENZO(A)PYRENE; ENVIRONMENTAL MONITORING; JAPAN; MUTAGENICITY TESTS; MUTAGENS; SOIL;

EID: 13844269358     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx049732l     Document Type: Article

References (45)

1. Kamiya, A., and Ose, Y. (1988) Isolation of dinitropyrene in emission gas from a municipal incinerator and its formation by a photochemical reaction. Sci. Total Environ. 72, 1-9.
2. Henderson, T. R., Sun, J. D., Royer, R. E., Clark, C. R., Li, A. P., Harvey, T. M., Hunt, D. H., Fulford, J. E., Lovette, A. M., and Davidson, W. R. (1983) Triple-quadrupole mass spectrometry studies of nitroaromatic emissions from different diesel engines. Environ. Sci. Technol. 17, 443-449.
3. Handa, T., Yamauchi, T., Sawai, K., Yamamura, T., Koseki, Y., and Ishii, T. (1984) In situ emission levels of carcinogenic and mutagenic compounds from diesel and gasoline engine vehicles on an expressway. Environ. Sci. Technol. 18, 895-902.
4. Höner, A., Arnold, M., Hüsers, N., and Kleiböhmer, W. (1995) Monitoring polycyclic aromatic hydrocarbons in waste gases. J. Chromatogr. A 710, 129-137.
5. Grimmer, G. (1983) Environmental Carcinogens: Polycyclic Aromatic Hydrocarbons, CRC Press, Boca Raton, FL.
6. Pitts, J. N., Jr. (1983) Formation and fate of gaseous and particulate mutagens and carcinogens in real and simulated atmospheres. Environ. Health Perspect. 47, 115-140.
7. Enya, T., Suzuki, H., Watanabe, T., Hirayama, T., and Hisamatsu, Y. (1997) 3-Nitrobenzanthrone, a powerful bacterial mutagen and suspected human carcinogen found in diesel exhaust and airborne particulates. Environ. Sci. Technol. 31, 2772-2776.
8. Cohen, A. J. (2000) Outdoor air pollution and lung cancer. Environ. Health Perspect. 47 (Suppl. 4), 115-140.
9. IARC (1987) IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. Supplement 7: Overall Evaluations of Carcinogenicity, an Updating of IARC Monographs, International Agency for Research on Cancer, Lyons, France.
10. Archer, V. E. (1990) Air pollution and fatal lung disease in three Utah counties. Arch. Environ. Health 45, 325-334.
11. Dockery, D. W., Pope, C. A., III, Xu, X., Spengler, J. D., Ware, J. H., Fay, M. E., Ferris, B. G., Jr., and Speizer, F. E. (1993) An association between air pollution and mortality in six U. S. cities. N. Engl. J. Med. 329, 1753-1759.
12. Pope, C. A., III, Thun, M. J., Namboodiri, M. M., Dockery, D. W., Evans, J. S., Speizer, F. E., and Heath, C. W., Jr. (1995) Particulate air pollution as a predictor of mortality in a prospective study of U. S. adults. Am. J. Respir. Crit. Care Med. 151, 669-674.
13. Barbone, F., Bovenzi, M., Cavalleri, F., and Stanta G. (1995) Air pollution and lung cancer in Trieste, Italy. Am. J. Epidermiol. 141, 1161-1169.
14. Pope, C. A., III, Burnett, R. T., Thun, M. J., Calle, E. E., Krewski, D., Ito, K., and Thurston, G. D. (2002) Lung cancer, cardiopulmonary mortality, and long-term exposure to fine particulate air pollution. J. Am. Med. Assoc. 287, 1132-1141.
15. Pope, C. A., III, Burnett, R. T., Thurston, G. D., Thun, M. J., Calle, E. E., Krewski, D., and Goldleski, J. J. (2004) Cardiovascular mortality and long-term exposure to particulate air pollution, epidemiological evidence of general pathophysiological pathways of disease. Circulation 109, 71-77.
16. Edenharder, R., Ortseifen, M., Koch, M., and Wesp, H. F. (2000) Soil mutagens are airborne mutagens: Variation of mutagenic activities induced in Salmonella typhimurium TA98 and TA100 by organic extracts of agricultural and forest soils in dependence on location and season. Mutat. Res. 472, 23-36.
17. Watanabe, T., Goto, S., Matsumoto, Y., Asanoma, M., Hirayama, T., Sera, N., Takahashi, Y., Endo, O., Sakai, S., and Wakabayashi, K. (2000) Mutagenic activity of surface soil and quantification of 1,3-, 1,6-, and 1,8-dinitropyrene isomers in soil in Japan. Chem. Res. Toxicol. 13, 281-286.
18. Nishimura, T., Goto, S., Kata, Y., Okunuki, M., and Matsushita, H. (1984) Mutagenicity and benzo[a]pyrene contents in soils in Tokyo. J. Jpn. Soc. Air Pollut. 19, 228-238.
19. Arashidani, K., Someya, T., Yoshikawa, M., and Kodama, Y. (1992) Polynuclear aromatic hydrocarbon concentration and mutagenic activity in soils sampled at the roadsides. J. Jpn. Soc. Air Pollut. 27, 190-197.
20. Tamakawa, K., Takahashi, Y., Mishima, Y., Seki, T., and Tsunoda, A. (1985) Mutagenicity and benzo[a]pyrene contents in soils in Sendai City; Influences of particulate substances produced by studded tires of automobiles. Eisei Kagaku 31, 329-333.
21. Wesp, H. F., Tang, X., and Edenharder, R. (2000) The influence of automobile exhausts on mutagenicity of soils: Contamination with, fractionation, separation, and preliminary identification of mutagens in the Salmonella/reversion assay and effects of solvent fractions on the sister-chromatid exchanges in human lymphocyte cultures and in the in vivo mouse bone marrow micronucleus. Mutat. Res. 472, 23-36.
22. Watanabe, T., Hasei, T., Takahashi, Y., Otake, S., Murahashi, T., Takamura, T., Hirayama, T., and Wakabayashi, K. (2003) Mutagenic activity and quantification of nitroarenes in surface soil in the Kinki region of Japan. Mutat. Res. 538, 121-131.
23. Goggleman, W., and Spitzauer, P. (1982) Mutagenic activity in agricultural soils. In Carcinogens and Mutagens in the Environment (Stich, H., Ed.), Vol. 3, pp 178-183, CRC Press, Orlando, FL.
24. Brown, K. W., Donnelly, K. C., Thomas, J. C., Davol, P., and Scott, B. R. (1985) Mutagenicity of three agricultural soils. Sci. Total Environ. 41, 173-186.
25. Knize, M. G., Takemoto, B. T., Lewis, P. R., and Felton, J. S. (1984) The characterization of the mutagenic activity of soil. Mutat. Res. 192, 23-30.
26. Misik, M., and Micieta, K. (2002) Tradescantia micronucleus and Vicia chromosome anatelophase assay in monitoring of genotoxicity of urban soil. Water Air Soil Pollut. 141, 181-187.
27. Endo, O., Goto, S., Matsumoto, Y., Sakai, S., Akutagawa, T., Asanoma, M., Hirayama, T., Watanabe, T., Tsukatani, H., Sera, N., Tada, A., and Wakabayashi, K. (2004) Mutagenicity of airborne particles, river waters and soils in Japan from 1996 to 2003. Environ. Mutagen. Res. 26, 9-22.
28. The Editorial Board of the Cancer Statistics in Japan, Ed. (2001) Cancer Statistics in Japan - 2001, Foundation for Promotion of Cancer Research, Tokyo.
29. Tokiwa, H., and Onishi, Y. (1986) Mutagenicity and carcinogenicity of nitroarenes and their sources in the environment. CRC Crit. Rev. Toxicol. 17, 23-60.
30. Takayama, S., Ishikawa, T., Nakajima, H., and Sato, S. (1985) Lung carcinoma induction in Syrian golden hamsters by intratracheal instillation of 1,6-dinitropyrene. Jpn. J. Cancer Res. 76, 457-461.
31. Maeda, T., Izumi, K., Otsuka, H., Manabe, Y., Kinouchi, T., and Onishi, Y. (1986) Induction of squamous cell carcinoma in the rat lung by 1,6-dinitropyrene. J. Natl. Cancer Inst. 76, 693-701.
32. Imaida, K., Lee, M. S., Wang, C. Y., and King, C. M. (1991) Carcinogenicities of dinitropyrenes in the female weanling CD rat. Carcinogenesis 12, 1187-1191.
33. Adachi, S., Kawamura, K., Takemoto, K., Suzuki, H., and Hisamatsu, Y. (2000) Carcinogenicity of 3-nitrobenzanthrone, a potent mutagen in diesel exhaust-preliminary results in F344 rats after intratracheal administration. In Relationships Between Respiratory Disease and Exposure to Air Pollution (Heinrich, U., and Mohr, U., Eds.) pp 315-319, ILSI Press, Washington, DC.
34. IARC (1989) International Agency for Research on Cancer Monograph 46, International Agency for Research on Cancer, Lyons, France.
35. Watanabe, T., Ishida, S., Minami, H., Kasai, T., Ogawa, S., Wakabayashi, K., and Hirayama, T. (1998) Identification of 1,6- and 1,8-dinitropyrene isomers as major mutagens in organic extracts of soil from Osaka, Japan. Chem. Res. Toxicol. 11, 1501-1507.
36. Yahagi, T., Nagao, M., Seino, Y., Matsushima, T., Sugimura, T., and Okada, M. (1977) Mutagenicity of N-nitrosamines on Salmonella. Mutat. Res. 48, 121-130.
37. Maron, D. M., and Ames, B. N. (1983) Revised methods for the Salmonella mutagenicity test. Mutat. Res. 113, 173-215.
38. Watanabe, M., Ishidate, M., Jr., and Nohmi, T. (1990) Sensitive method for detection of mutagenic nitroarenes and aromatic amines: New derivatives of Salmonella typhimurium tester strains possessing elevated O-acetyltransferase levels. Mutat. Res. 234, 337-348.
39. McCoy, E. C., Anders, M., and Rosenkranz, H. S. (1983) The basis of the insensitivity of Salmonella typhimurium strain TA98/1,8-DNP6 to the mutagenic action of nitroarenes. Mutat. Res. 121, 17-23.
40. Spitzer, T. (1993) Selective cleanup for polynuclear aromatic compounds in airborne particles and soil. J. Chromatogr. 643, 43-49.
41. Spitzer, T., and Kuwatsuka, S. (1986) Simple method for determination of polynuclear aromatic hydrocarbons in soil by cleanup on XAD-2. J. Chromatogr. 358, 434-437.
42. U.S. Department of Health and Human Services (1998) Eighth report on carcinogens. Full Report, National Toxicology Program, U.S. Department of Health and Human Services, Washington, DC.
43. Hayakawa, K., Murahashi, T., Butoh, M., and Miyazaki, M. (1995) Determination of 1,3-, 1,6- and 1,8-dinitropyrenes and 1-nitropyrene in urban air by high-performance liquid chromatography using chemiluminescence detection. Environ. Sci. Technol. 29, 25-29.
44. Hisamatsu, Y., Nishimura, T., Tanabe, K., and Matsushita, H. (1986) Mutagenicity of the photochemical reaction products of pyrene with nitrogen dioxide. Mutat. Res. 172, 19-27.
45. Einisto, P., Watanabe, M., Ishidate, M., Jr., and Nomi, T. (1991) Mutagenicity of 30 chemicals in Salmonella typhimurium strains possessing different nitroreductase or O-acetyltransferase activities. Mutat. Res. 259, 95-102.