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

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.Search in Google Scholar

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.Search in Google Scholar

Falter B, Kutzer C, Richter E. (1994). Biomonitoring of hemoglobin adducts: aromatic amines and tobacco-specific nitrosamines. Clin Investig 72: 364-371.Search in Google Scholar

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.Search in Google Scholar

Hauthal HG. (1993). Rosenmontag und die Folgen die Stöfälle der Hoechst AG. Nach. Chem Tech Lab 41: 440.Search in Google Scholar

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.Search in Google Scholar

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.Search in Google Scholar

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/cccc20040589Search in Google Scholar

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/tx049972115144223Search in Google Scholar

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/v10102-010-0045-8299402321218119Search in Google Scholar

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/tx800112718624415Search in Google Scholar

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.Search in Google Scholar

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.Search in Google Scholar

Purohit V and Basu A. (2000). Mutagenicity of nitroaromatic compounds. Chem Res Toxicol 13: 673-692.10.1021/tx000002x10956054Search in Google Scholar

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/s00420010024311563605Search in Google Scholar

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.2005.077Search in Google Scholar

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.116112955743Search in Google Scholar

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)00295-0Search in Google Scholar

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/bgh061Search in Google Scholar

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.21122Search in Google Scholar

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.Search in Google Scholar

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.Search in Google Scholar

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.Search in Google Scholar

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.Search in Google Scholar

U.S. Department of Health and Human Services. (2004). 11^th Report on Carcinogens, U.S. Government Printing Office, Washington, DC.Search in Google Scholar

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.Search in Google Scholar