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Genotoxic mechanisms for the carcinogenicity of the environmental pollutants and carcinogens o-anisidine and 2-nitroanisole follow from adducts generated by their metabolite N-(2-methoxyphenyl)hydroxylamine with deoxyguanosine in DNA Cover

Genotoxic mechanisms for the carcinogenicity of the environmental pollutants and carcinogens o-anisidine and 2-nitroanisole follow from adducts generated by their metabolite N-(2-methoxyphenyl)hydroxylamine with deoxyguanosine in DNA

Open Access
|Jun 2009

References

  1. Branner B, Kutzer C, Zwickenpflug W, Scherer G, Heller W-D, Richter E. (1998). Haemoglobin adducts from aromatic amines and tobacco-specific nitrosamines in pregnant smoking and non-smoking women. Biomarkers 3: 35-47.
  2. Dračínská H, Mikšanová M, Svobodová M Smrček S, Frei E, Schmeiser HH, Stiborová M. (2006). Oxidative detoxication of carcinogenic 2-nitroanisole by human, rat and rabbit cytochrome P450. Neuro Endocrinol. Lett., 27: 9-13.
  3. Falter B, Kutzer C, Richter E. (1994). Biomonitoring of hemoglobin adducts: aromatic amines and tobacco-specific nitrosamines. Clin Investig 72: 364-371.
  4. Garner RC, Martin CN, Clayson DB. (1984). (2nd ed. Searle C, Ed.) Carcinogenic aromatic amines and related compounds. Chemical Carcinogens, ACS Monograph 182, Vol. 1: pp. 175-302, American Chemical Society, Washington, DC.
  5. Hauthal HG. (1993). Rosenmontag und die Folgen die Stöfälle der Hoechst AG. Nach. Chem Tech Lab 41: 440.
  6. IARC. (1982). Ortho- and para-anisidine and their hydrochlorides. IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, No. 27, IARC, Lyon.
  7. IARC. (2006). Formaldehyde, 2-butoxyethanol and 1-terc-butoxypropan-2-ol. IARC Monographs on the Evaluation of Carcinogenic Risk to Humans, Vol. 88, pp. 39-325, IARC, Lyon.
  8. Mikšanová M, Novák P, Frei E, Stiborová M. (2004a). Metabolism of carcinogenic 2-nitroanisole by rat, rabbit, porcine and human hepatic cytosol. Collect Czech Chem Commun 69: 589-602.10.1135/cccc20040589
  9. Mikšanová M, Sulc M, Rýdlová H, Schmeiser HH, Frei E, Stiborová M. (2004b). Enzymes involved in the metabolism of the carcinogen 2-nitroanisole: evidence for its oxidative detoxication by human cytochromes P450. Chem. Res. Toxicol., 17: 663-671.10.1021/tx049972115144223
  10. Naiman K, Dračínská H, Dračínský M, Martínková M Martínek V, Hodek P, Štícha M, Frei E, Stiborová M. (2008a). Cytochrome P450-mediated metabolism of N-(2-methoxyphenyl)-hydroxylamine, a human metabolite of the environmental pollutants and carcinogens o-anisidine and o-nitroanisole Interdisc. Toxicol., 1: 218-224.10.2478/v10102-010-0045-8299402321218119
  11. Naiman K, Dračínská H, Martínková M, Šulc M, Dračínský M, Kejíková L, Hodek P, Hudeček J, Liberda J, Schmeiser HH, Frei E, Stiborová M. (2008b). Redox cycling in the metabolism of the environmental pollutant and suspected human carcinogen o-anisidine by rat and rabbit hepatic microsomes. Chem Res Toxicol 21: 1610-1621.10.1021/tx800112718624415
  12. NTP. (1978). Bioassay of o-anisidine hydrochloride for possible carcinogenicity. NTP Technical Report 89, National Institute of Health, US Department of Health and Human Services, Bethesda, MD.
  13. NTP. (1993). Toxicology and Carcinogenesis. Studies of 2-nitroanisole. NTP Technical Report 416, National Institute of Health, US Department of Health and Human Services, Bethesda, MD.
  14. Purohit V and Basu A. (2000). Mutagenicity of nitroaromatic compounds. Chem Res Toxicol 13: 673-692.10.1021/tx000002x10956054
  15. Richter E, Rosler S, Scherer G, Gostomzyk JG, Grubl A, Kamer U, Behrendt H. (2001). Haemoglobin adducts from aromatic amines in children in relation to area of residence and exposure to environmental tobacco smoke. Int Arch Occup Environ Health 74: 421-428.10.1007/s00420010024311563605
  16. Rýdlová H, Mikšanová M, Ryšlavá H, Stiborová M. 2005. Carcinogenic pollutants o-nitroanisole and o-anisidine are substrates and inducers of cytochromes P450. Biomed Papers 49: 441-447.10.5507/bp.2005.077
  17. Stabbert R, Schäfer K-H, Biefel C, Rustemeier K. (2003). Analysis of aromatic amines in cigarette smoke. Rapid Commun Mass Spectrom 17: 2125-2132.10.1002/rcm.116112955743
  18. Stiborová M, Mikšanová M, Havlíček V, Schmeiser HH, Frei E. (2002). Mechanism of peroxidase-mediated oxidation of carcinogenic o-anisidine and its binding to DNA. Mutat Res 500: 49-66.10.1016/S0027-5107(01)00295-0
  19. Stiborová M, Mikšanová M, Smrček S, Bieler CA, Breuer A, Klokow KA, Schmeiser HH, Frei E. (2004). Identification of a genotoxic mechanism for 2-nitroanisole carcinogenicity and of its carcinogenic potential for humans. Carcinogenesis 25: 833-840.10.1093/carcin/bgh061
  20. Stiborová M, Mikšanová M, Šulc M, Rýdlová H, Schmeiser HH, Frei E. (2005). Identification of a genotoxic mechanism for the carcinogenicity of the environmental pollutant and suspected human carcinogen o-anisidine. Int J Cancer 116: 667-678.10.1002/ijc.21122
  21. Stiborová M, Schmeiser HH, Breuer A, Frei E. (2001). Evidence for activation of carcinogenic o-anisidine by prostaglandin H synthase: 32P-postlabelling analysis of DNA adducts formation. Gen Physiol Biophys 20: 267-279.
  22. Stiborová M, Schmeiser HH, Frei E. (1998). To the mechanism of 2-nitroanisole carcinogenicity: in vitro metabolism of 2-nitroanisole mediated by peroxidases and xanthine oxidase. Collect Czech Chem Commun 63: 857-869.
  23. Svobodová M, Dračínská H, Martínková M, Hudeček J, Hodek P, Frei E, Stiborová M. (2008). Oxidation of carcinogenic 2-nitroanisole by rat cytochrome P450 — similarity between human and rat systems. Interdisc. Toxicol., 1: 180-185.
  24. Traupe H, Menge G, Kandt J, Karmaus W. (1997). Higher frequency of atopic dermatitis and decrease in viral warts among children exposed to chemicals liberated in a chemical accident in Frankfurt, Germany. Dermatology 195: 112-118.
  25. U.S. Department of Health and Human Services. (2004). 11th Report on Carcinogens, U.S. Government Printing Office, Washington, DC.
  26. Weiss T, Angerer J. (2003). Simultaneous determination of various aromatic amines and metabolites of aromatic nitro compounds in urine for low level exposure using gas chromatography-mass spectrometry. J Chromatogr B 778: 179-192.
DOI: https://doi.org/10.2478/v10102-009-0004-4 | Journal eISSN: 1337-9569 | Journal ISSN: 1337-6853
Language: English
Page range: 24 - 27
Published on: Jun 19, 2009
Published by: Slovak Academy of Sciences, Institute of Experimental Pharmacology & Toxicology, Centre of Experimental Medicine
In partnership with: Paradigm Publishing Services
Publication frequency: 4 issues per year

© 2009 Marie Stiborová, Karel Naiman, Markéta Martínková, Václav Martínek, Martina Svobodová, Heinz Schmeiser, Eva Frei, published by Slovak Academy of Sciences, Institute of Experimental Pharmacology & Toxicology, Centre of Experimental Medicine
This work is licensed under the Creative Commons License.

Volume 2 (2009): Issue 1 (March 2009)