Cytochrome P450-mediated metabolism of N-(2-methoxyphenyl)-hydroxylamine, a human metabolite of the environmental pollutants and carcinogens o-anisidine and o-nitroanisole

Balaban AT, Garfield RE, Lesko MJ, Seitz WA. (1998) Synthesis and spectral data of some new N-nitroso-N-phenylhydroxylamine (cupferron) derivatives. Org Prep Proced Int 30: 439-446.10.1080/00304949809355306Search in Google Scholar

Beland FA, Fullerton NF, Heflich RH. (1984) Rapid isolation, hydrolysis and chromatography of formaldehyde-modified DNA. J Chromatogr 308: 121-131.10.1016/0378-4347(84)80202-9Search in Google Scholar

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: 35-47.10.1080/13547509823135423899255Search in Google Scholar

Brennan RJ, Schiestl RH. (1997). Aniline and its metabolite generate free radicals in yeast. Mutagenesis 12: 215-220.Search in Google Scholar

Brennan RJ, Schiestl RH. (1999) The aromatic amine carcinogens o-toluidine and o-anisidine induce free radicals and intrachromosomal recombination in Saccharomyces cerevisiae. Mutat Res 430: 37-45.Search in Google Scholar

Cheng G, Shi Y, Sturla S, Jalas J, McIntee EJ, Villalta PW, Wang M, Hecht SS. (2003) Reactions of formaldehyde plus acetaldehyde with deoxyguanosine and DNA: Formation of cyclic deoxyguanosine adducts and formaldehyde cross-links. Chem Res Toxicol 16: 145-152.10.1021/tx025614r12588185Search in Google Scholar

Dhareshwar SS, Stella VJ. (2008) Your prodrug releases formaldehyde: Should you be concerned? No! J Pharm Sci 97: 4184-4193.10.1002/jps.2131918288723Search in Google Scholar

Falter B, Kutzer C, Richter E. (1994) Biomonitoring of hemoglobin adducts: aromatic amines and tobacco-specific nitrosamines. Clin Investig 72: 364-371.10.1007/BF002528298086771Search 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 Störfälle der Hoechst AG. Nach. Chem Tech Lab 41: 440.Search in Google Scholar

Hodek P, Jansčák P, Anzenbacher P, Burkhard J, Janků J, Vodička L. (1988) Metabolism of diamantane by rat-liver microsomal-cytochromes P-450. Xenobiotica 18: 1109-1118.10.3109/004982588090422333242307Search in Google Scholar

Huang H, Hopkins PB. (1993) DNA interstrand cross-linking by formaldehyde: nucleotide sequence preference and covalent structure of the predominant cross-link formed in synthetic oligonucleotides. J Am Chem Soc 115: 9402-9408.10.1021/ja00074a005Search in Google Scholar

Imaoka S, Osada M, Minamiyama Y, Yukimura T, Toyokuni S, Takemura S, Hiroi T, Funae Y. (2004) Role of phenobarbital-inducible cytochrome P450s as a source of active oxygen species in DNA-oxidation. Cancer Lett 203: 117-125.10.1016/j.canlet.2003.09.00914732219Search 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

Kim D, Kadlubar FF, Teitel CH, Guengerich FP. (2004) Formation and reduction of aryl and heterocyclic nitroso compounds and significance in the flux of hydroxylamines. Chem Res Toxicol 17: 529-536.10.1021/tx034267y15089095Search in Google Scholar

Kirchner G, Bayer U. (1992) Genotoxic activity of the aminophenols as evidenced by the induction of sister chromatid exchanges. Hum Toxicol 1: 387-392.Search in Google Scholar

Mikšanová M, Novák P, Frei E, Stiborová M. (2004) 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

Naiman K, Dračínská H, Martínková M, Šulc M, Dračínský M, Kejíková L, Hodek P, Hudeček J, Liberda J, Schmeiser HH, Frei E, Stiborová M. (2008) 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/tx8001127Search 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

Okhuma Y, Kawanishi S. (2001) Oxidative DNA damage induced by a metabolite of carcinogenic o-anisidine: enhancement of DNA damage and alteration in its sequence specificity by superoxide dismutase. Arch Biochem Biophys 389: 49-56.Search in Google Scholar

Omura T, Sato R. (1964) The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem 239: 2370-2378.Search 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/s004200100243Search 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

Sasaki YF, Nishidate E, Su YQ, Matsusaka N, Tsuda S, Susa N, Furukawa Y, Ueno S. (1998) Organ-specific genotoxicity of the potent rodent bladder carcinogens o-anisidine and p-cresidine. Mutat Res 412: 155-160.10.1016/S1383-5718(97)00183-6Search in Google Scholar

Seidenfaden W. (1971) Methoden der Organischen Chemie (Houben-Weyl), Band X/1, Georg Thieme Verlag, Stuttgart, p. 1058.Search in Google Scholar

Sottocasa GL, Kuylenstierna I, Ernster I, Bergstrand A. (1967) An electron transport system associated with the outer membrane of liver mitochondria. J Cell Biol 32: 415-438.10.1083/jcb.32.2.415Search 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.1161Search in Google Scholar

Stiborová M, Asfaw B, Anzenbacher P, Lešetický L, Hodek P. (1988) The first identification of the benzenediazonium ion formation from a non-aminoazo dye, 1-phenylazo-2-hydroxynaphthalene (Sudan I) by microsomes of rat livers. Cancer Lett 40: 319-326.10.1016/0304-3835(88)90091-2Search in Google Scholar

Stiborová M, Asfaw B, Frei E, Schmeiser HH, Wiessler M. (1995) Benzenediazonium ion derived from Sudan I forms an 8-(phenylazo)guanine adduct. Chem Res Toxicol 8: 489-498.10.1021/tx00046a002Search 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.Search 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: 857-869.10.1135/cccc19980857Search 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: 112-118.10.1159/000245711Search 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

Wiechelman KJ, Braun RD, Fitzpatrick JD. (1988) Investigation of the bicinchoninic acid protein assay: identification of the groups responsible for color formation. Anal Biochem 175: 231-237.10.1016/0003-2697(88)90383-1Search in Google Scholar

Yang CS, Tu YY, Koop DR, Coon MJ. (1985) Metabolism of nitrosamines by purified rabbit liver cytochrome P-450 isozymes. Cancer Re. 45: 1140-1145.Search in Google Scholar