Rat cytochromes P450 oxidize 3-aminobenzanthrone, a human metabolite of the carcinogenic environmental pollutant 3-nitrobenzanthrone

Interdisciplinary Toxicology

Volumn 1, Issue 2, 2008, Pages 150-154

  Mizerovská, Jana ^a   Dračnská, Helena ^a   Hudeček, Jiří ^a   Hodek, Petr ^a   Stiborová, Marie ^a   Arlt, Volker M ^b   Schmeiser, Heinz H ^c   Frei, Eva ^c  

^a CHARLES UNIVERSITY   (Czech Republic)

^b INSTITUTE OF CANCER RESEARCH   (United Kingdom)

^c GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

Author keywords

3 aminobenzanthrone; 3 nitrobenzanthrone; cytochrome P450; HPLC; induction; inhibition; oxidation

Indexed keywords

EID: 77349124823     PISSN: 13376853     EISSN: 13379569     Source Type: Journal    
DOI: 10.2478/v10102-010-0031-1     Document Type: Article

References (27)

1. Arlt VM (2005) 3-Nitrobenzanthrone, a potential human cancer hazard in diesel exhaust and urban air pollution: A review of the evidence. Mutagenesis 20: 399-410.
2. Arlt VM, Bieler CA, Mier W, Wiessler M and Schmeiser HH (2001) DNA adduct formation by the ubiquitous environmental contaminant 3-nitrobenzanthrone in rats determined by 32P-postlabeling. Int J Cancer 93: 450-454.
3. Arlt VM, Cole KJ and Phillips DH (2004a) Activation of 3-nitrobenzanthrone and its metabolites to DNA-damaging species in human B-lymphoblastoid MCL-5 cells. Mutagenesis 19: 149-156.
4. Arlt VM, Glatt HR, Muckel E, Pabel U, Sorg BL, Schmeiser HH and Phillips DH (2002) Metabolic activation of the environmental contaminant 3-nitrobenzanthrone by human acetyltransferases and sulfotransferase. Carcinogenesis 23: 1937-1945.
5. Arlt VM, Glatt H, Muckel E, Pabel U, Sorg BL, Seidel A, Frank H, Schmeiser HH and Phillips DH (2003a) 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.
6. Arlt VM, Henderson CJ, Wolf CR, Schmeiser HH, Phillips DH and Stiborova M (2006a) Bioactivation of 3-aminobenzanthrone, a human metabolite of the environmental pollutant 3-nitrobenzanthrone: evidence for DNA adduct formation mediated by cytochrome P450 enzymes and peroxidases. Cancer Lett 234: 220-231.
7. Arlt VM, Hewer A, Sorg BL, Schmeiser HH, Phillips DH and Stiborova M (2004b) 3-Aminobenzanthrone, a human metabolite of the environmental pollutant 3-nitrobenzanthrone, forms DNA adducts after metabolic activation by human and rat liver microsomes: evidence for activation by cytochrome P450 1A1 and P450 1A2. Chem Res Toxicol 17: 1092-1101.
8. Arlt VM, Schmeiser HH, Osborne MR, Kawanishi M, Kanno T, Yagi T, Phillips DH and Takamura-Enya T (2006b) Identification of three major DNA adducts formed by the carcinogenic air pollutant 3-nitrobenzanthrone in rat lung at the C8 and N2 position of guanine and at the N6 position of adenine. Int J Cancer 118: 2139-2146.
9. Arlt VM, Sorg BL, Osborne M, Hewer A, Seidel A, Schmeiser HH and Phillips DH (2003b) DNA adduct formation by the ubiquitous environmental pollutant 3-nitrobenzanthrone and its metabolites in rats. Biochem Biophys Res Commun 300: 107-114.
10. Arlt VM, Stiborova M, Henderson CJ, Osborne MR, Bieler CA, Frei E, Martinek V, Sopko B, Wolf CR, Schmeiser HH and Phillips DH (2005) The environmental pollutant and potent mutagen 3-nitrobenzanthrone forms DNA adducts after reduction by NAD(P)H:quinone oxidoreductase and conjugation by acetyltransferases and sulfotransferases in human hepatic cytosols. Cancer Res 65: 2644-2652.
11. Arlt VM, Stiborova M, Hewer A, Schmeiser HH and Phillips DH, (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.
12. Arlt, VM, Zhan L, Schmeiser HH, Honma M, Hayashi M, Phillips DH and Suzuki T (2004c) DNA adducts and mutagenic specificity of the ubiquitous environmental pollutant 3-nitrobenzanthrone in Muta Mouse. Environ Mol Mutagen 43: 186-195.
13. Bieler CA, Cornelius M, Klein R, Arlt VM, Wiessler M, Phillips DH and Schmeiser HH (2005) DNA adduct formation by the environmental contaminant 3-nitrobenzanthrone after intratracheal instillation in rats. Int J Cancer 118: 833-838.
14. Bieler CA, Cornelius MG, Stiborova M, Arlt VM, Wiessler M, Phillips DH and Schmeiser HH (2007) Formation and persistence of DNA adducts formed by the carcinogenic air pollutant 3-nitrobenzanthrone in target and non-target organs after intratracheal instillation in rats. Carcinogenesis 28: 1117-1121.
15. Bieler CA, Wiessler M, Erdinger L, Suzuki H, Enya T and Schmeiser HH (1999) DNA adduct formation from the mutagenic air pollutant 3-nitrobenzanthrone. Mutat Res 439: 307-311.
16. Borlak J, Hansen T, Yuan Z, Sikka HC, 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 Aromat Compounds 21: 73-86.
17. 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 exhausts and airborne particulates. Environ Sci Technol 31: 2772-2776.
18. Grabchev I, Moneva I, Betcheva R and Elyashevich G (2002) Colored microporous polyethylene films: effect of porous structure on dye adsorption. Mat Res Innovat 6: 34-37.
19. Hansen T, Seidel A and Borlak J (2007) The environmental carcinogen 3-nitrobenzanthrone and its main metabolite 3-aminobenzanthrone enhance formation of reactive oxygen intermediates in human A549 lung epithelial cells. Toxicol Appl Pharmacol 221: 222-234.
20. Nagy E, Zeisig M, Kawamura K, Hisumatsu Y, Sugeta A, Adachi S and Moller L (2005) DNA-adduct and tumor formations in rats after intratracheal administration of the urban air pollutant 3-nitrobenzanthrone. Carcinogenesis 26: 1821-1828.
21. Rendic S and DiCarlo FJ (1997) Human cytochrome P450 enzymes: A status report summarizing their reactions, substrates, inducers, and inhibitors. Drug Metab Rev 29: 413-480.
22. 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.
23. Stiborova M, Dračinska H, Hajkova J, Kadeřabkova P, Frei E, Schmeiser HH, Souček P, Phillips DH and Arlt VM (2006) The environmental pollutant and carcinogen 3-nitrobenzanthrone and its human metabolite 3-aminobenzanthrone are potent inducers of rat hepatic cytochromes P450 1A1 and -1A2 and NAD(P)H:quinone oxidoreductase. Drug Metab Dispos 34: 1398-1405.
24. Stiborova M, Dračinska H, Mizerovska J, Frei E, Schmeiser HH, Hudeček J, Hodek P, Phillips DH and Arlt VM 2008 The environmental pollutant and carcinogen 3-nitrobenzanthrone induces cytochrome P450 1A1 and NAD(P)H:quinone oxidoreductase in rat lung and kidney, thereby enhancing its own genotoxicity. Toxicology 247: 11-22.
25. Stiborova M, Martinek V, Rydlova H, Hodek P and Frei E (2002) Sudan I is a potential carcinogen for humans: evidence for its metabolic activation and detoxication by human recombinant cytochrome P450 1A1 and liver microsomes. Cancer Res 62: 5678-5684.
26. Svobodova M, šistkova J, Dračinska H, Hudeček J, Hodek P, Schmeiser HH, Arlt VM, Frei E and Stiborova M (2007) Reductive activation of environmental pollutants 3-nitrobenzanthrone and 2-nitrobenzanthrone. Chem Listy 100: s277-s279.
27. Sykora J, Mudago V, Hutterer R, Nepras M, Vanerka J, Kapusta P, Fidler V and Hof M (2002) ABA-C-15: A new dye for probing solvent relaxation in phospholipid bilayers. Langmuir 18: 9276-9282.