Activation of 3-nitrobenzanthrone and its metabolites to DNA-damaging species in human B lymphoblastoid MCL-5 cells

Mutagenesis

Volumn 19, Issue 2, 2004, Pages 149-156

  Arlt, Volker M ^a   Cole, Kathleen J ^a   Phillips, David H ^a  

^a INSTITUTE OF CANCER RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3 NITROBENZANTHRONE; HYDROXYUREA; MUTAGENIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; CELL VIABILITY; CHEMICAL STRUCTURE; CHROMOSOME DAMAGE; COMET ASSAY; CONCENTRATION (PARAMETERS); CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA ADDUCT; DNA BINDING; DNA DAMAGE; DNA STRAND BREAKAGE; GENOTOXICITY; HUMAN; HUMAN CELL; INCUBATION TIME; LYMPHOBLASTOID CELL LINE; MICRONUCLEUS TEST; NONHUMAN; PRIORITY JOURNAL; RAT;

BENZ(A)ANTHRACENES; COMET ASSAY; DNA ADDUCTS; HUMANS; LYMPHOCYTES; MICRONUCLEI, CHROMOSOME-DEFECTIVE; MUTAGENS;

SALMONELLA TYPHIMURIUM;

EID: 1642330755     PISSN: 02678357     EISSN: None     Source Type: Journal    
DOI: 10.1093/mutage/geh008     Document Type: Article

References (37)

1. Adachi,S., Kawanura,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 Heinrich,U. and Mohr,U. (eds), Relationships between Respiratory Disease and Exposure to Air Pollution. ILSI Press, Washington, DC, pp. 315-319.
2. 32p-postlabeling. Int. J. Cancer, 93, 450-454.
3. Arlt,V.M., Schmeiser,H.H. and Pfeifer,G.P. (2001b) Sequence-specific detection of aristolochic acid-DNA adducts in the human p53 gene by terminal transferase-dependent PCR. Carcinogenesis, 22, 133-140.
4. Arlt,V.M., Glatt,H.R., Muckel,E., Pabel,U., Sorg,B.L., Schmeiser,H.H. and Phillips,D.H. (2002) Metabolic activation of the environmental contaminant 3-nitrobenzanthrone by human acetyltransferases and sulfotransferase. Carcinogenesis, 23, 1937-1945.
5. Arlt,V.M., Sorg,B.,L., Osborne,M., Hewer,A., Seidel,A., Schmeiser,H.H. and Phillips,D.H. (2003a) DNA adduct formation by the ubiquitous environmental pollutant 3-nitrobenzanthrone and its metabolites in rats. Biochem. Biophys. Res. Commun., 300, 107-114.
6. Arlt,V.M., Glatt,H., Muckel,E., Pabel,U., Sorg,B.L., Seidel,A., Frank,H., Schmeiser,H.H. and Phillips,D.H. (2003b) Activation of 3-nitrobenzanthrone and its metabolites by human acetyltransferases, sulfotransferases and cytochrome P450 expressed in Chinese hamster V79 cells. Int. J. Cancer, 105, 583-592.
7. Arlt,V.M., Stiborova,M., Hewer,A., Schmeiser,H.H. and Phillips,D.H. (2003c) Human enzymes involved in the metabolic activation of the environmental contaminant 3-nitrobenzanthrone: Evidence for reductive activation by human NADPH: cytochrome P450 reductase. Cancer Res., 63, 2752-2761.
8. Bieler,C.A., Wiessler,M., Erdinger,L., Suzuki,H., Enya,T. and Schmeiser,H.H. (1999) DNA adduct formation from the mutagenic air pollutant 3-nitrobenzanthrone. Mutat. Res., 439, 307-311.
9. Bieler,C.A., Arlt,V.M., Wiessler,M. and Schmeiser,H.H. (2003) DNA adduct formation by the environmental contaminant 3-nitrobenzanthrone in V79 cells expressing human cytochrome P450 enzymes. Cancer Lett., 200, 9-18.
10. Borlak,J., Hansen,T., Yuan,Z., Sikka,H.C., Kumar,S., Schmidbauer,S., Frank,H., Jacob.J. and Seidel,A. (2000) Metabolism and DNA-binding of 3-nitrobenzanthrone in primary rat alveolar type II cells, in human fetal bronchial, rat epithelial and mesenchymal cell lines. Polycyclic Aromatic Compounds, 21, 73-86.
11. Busby,W.F.,Jr, Penman,B.W. and Crespi,C.L. (1994) Human cell mutagenicity of mono- and dinitropyrenes in metabolically competent MCL-5 cells. Mutat. Res., 322, 233-242.
12. Busby,W.F.,Jr, Smith,H., Crespi,C.L., Penman,B.W. and Lafleur,A.L. (1997) Mutagenicity of the atmospheric transformation products 2-nitrofluoranthene and 2-nitrodibenzopyranone in Salmonella and human cell forward mutation assays. Mutat. Res., 389, 261-270.
13. Chae,Y.H., Yun,C.H., Guengerich,F.P., Kadlubar,F.F. and El-Bayoumy,K. (1993) Roles of human hepatic and pulmonary cytochrome P450 enzymes in the metabolism of the environmental carcinogen 6-nitrochrysene. Cancer Res., 53, 2028-2034.
14. Chae,Y.H., Thomas,T., Guengerich,F.P., Fu,P.P. and El-Bayoumy,K. (1999) Comparative metabolism of 1-, 2- and 4-nitropyrene by human hepatic and pulmonary microsomes. Cancer Res., 59, 1473-1480.
15. Crespi,C.L., Gonzalez,F.J., Steimel,D.T., Turner,T.R., Gelboin,H.V., Penman,B.W. and Langenbach,R. (1991) A metabolically competent human cell line expressing five cDNAs encoding procarcinogen-activating enzymes: Application to mutagenicity testing. Chem. Res. Toxicol., 4, 566-572.
16. Crofton-Sleigh,C., Doherty,A., Ellard,S., Parry,E.M. and Venitt,S. (1993) Micronucleus assay using cytochalasin-blocked MCL-5 cells, a proprietary human cell line expressing five human cytochromes P-450 and microsomal eposide hydrolase. Mutagenesis, 8, 363-372.
17. Enya,J., Suzuki,H., Watanabe,T., Hirayama,T. and Hisamatsu,Y. (1997) 3-Nitrobenzanthrone, a powerful bacterial mutagen and suspected human carcinogen found in diesel exhausts and airborne particulates. Environ. Sci. Technol., 31, 2772-2776.
18. Enya,T., Kawanishi,M., Suzuki,H., Matsui,S. and Hisamatsu,Y. (1998) An unusual DNA adduct derived from the powerfully mutagenic environmental contaminant 3-nitrobenzanthrone. Chem. Res. Toxicol., 11, 1460-1467.
19. Farmer,P.B. (1997) Diesel fuel and exhaust emissions: Is there a human carcinogenic risk? Lancet, 350, 1118.
20. Fenech,M. (2000) The in vitro micronucleus technique. Mutat. Res., 455, 81-95.
21. Feilberg,A., Ohura,T., Nielsen.J., Poulsen,M.W.B. and Amagai,T. (2002) Occurrence and photostability of 3-nitrobenzanthrone associated with atmospheric particles. Atmos. Environ., 36, 3591-3600.
22. IARC (1989) IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, no. 46, Diesel and Gasoline Engine Exhausts and Some Nitroarenes. IARC, Lyon.
23. Kawanishi,M., Enya.T., Suzuki,H., Takebe,H., Matsui,S. and Yagi,T. (2000) Postlabelling analysis of DNA adducts formed in human hepatoma cells treated with 3-nitrobenzanthrone. Mutat. Res., 470, 133-139.
24. Martin,F.L., Cole,K.J., Orme,M.H., Grover,P.L., Phillips,D.H. and Venitt,S. (1999) The DNA repair inhibitors hydroxyurea and cytosine arabinoside enhance the sensitivity of the alkaline single-cell gel electrophoresis ('comet') assay in metabolically-competent MCL-5 cells. Mutat. Res., 445, 21-43.
25. Murahashi,T. (2003) Determination of mutagenic 3-nitrobenzanthrone in diesel exhaust particulate matter by three-dimensional high-performance liquid chromatography. Analyst, 128, 42-45.
26. Murahashi,T., Watanabe,T., Otake,S., Hattori,Y., Takamura,T., Wakabayashi,K. and Hirayama,T. (2003) Determination of 3-nitrobenzanthrone in surface soil by normal-phase high-performance liquid chromatography with fluorescence detection. J. Chromatogr., 992A, 101-107.
27. Pfau,W., Martin,F.A., Cole,K.J., Venitt,S., Phillips,D.H., Grover,P.L. and Marquardt,H. (1999) Heterocyclic aromatic amines induce DNA strand breaks and cell transformation. Carcinogenesis, 20, 545-551.
28. Phousongphouang,P.T., Grosovsky,A.J., Eastmond,D.A., Covarrubias,M. and Arey,J. (2000) The genotoxicity of 3-nitrobenzanthrone and the nitropyrene lactones in human lymphoblasts. Mutat. Res., 472, 93-103.
29. Purohit,V. and Basu,A.K. (2000) Mutagenicity of nitroaromatic compounds. Chem. Res. Toxicol., 13, 673-692.
30. Seidel,A., Dahmann,D., Krekeler,H. and Jacob,J. (2002) Biomonitoring of polycyclic aromatic compounds in the urine of mining workers occupationally exposed to diesel exhaust. Int. J. Hyg. Environ. Health, 204, 333-338.
31. Singh,N.P., McCoy,M.T., Tice,R.R. and Schneider,E.L. (1988) A simple technique for quantization of low levels of DNA damage in individual cells. Esp. Cell Res., 175, 184-191.
32. Stiborova,M., Frei,E., Wiessler,M. and Schmeiser,H.H. (2001) Human enzymes involved in the metabolic activation of carcinogenic aristolochic acids: Evidence for reductive activation by cytochromes P540 1A1 and 1A2. Chem. Res. Toxicol., 14, 1128-1137.
33. Tice,R.R., Agurell,E., Anderson,D., Burlinson,B., Hartmann,A., Kobayashi,H., Miyamae,Y., Rojas,E., Ryu,J.C. and Sasaki,Y.F. (2000) Single cell gel/comet assay: Guidelines for in vitro and in vivo genetic toxicology testing. Environ. Mol. Mutagen., 35, 206-221.
34. Tokiwa,H. and Ohnishi,Y. (1986) Mutagenicity and carcinogenicity of nitroarenes and their sources in the environment. CRC Crit. Rev. Toxicol., 17, 23-60.
35. Tokiwa,H., Sera,N., Horikawa,K., Nakanishi,Y. and Shigematu,N. (1993) The presence of mutagens/carcinogens in the excised lung and analysis of lung cancer induction. Carcinogenesis, 14, 1933-1938.
36. Watanabe,T., Hasei,T., Yoshifumi,T., 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.
37. Yaffe,D., Cohen,Y., Arey,J. and Grosovsky,A.J. (2001) Multimedia analysis of PAHs and nitro-PAH daughter products in the Los Angeles basin. Risk Anal., 21, 275-294.