Identification of rat cytochromes P450 metabolizing N-(2-methoxyphenyl) hydroxylamine, a human metabolite of the environmental pollutants and carcinogens o-anisidine and o-nitroanisole

Neuroendocrinology Letters

Volumn 31, Issue SUPPL. 2, 2010, Pages 36-45

  Naiman, Karel ^a   Frei, Eva ^b   Stiborova, Marie ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

^b GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

Author keywords

Cytochromes P450; Metabolism; N (2 methoxyphenyl)hydroxylamine; o aminophenol; o anisidine

Indexed keywords

CARCINOGEN; CYTOCHROME B5 REDUCTASE; CYTOCHROME P450; CYTOCHROME P450 2A; CYTOCHROME P450 2C; CYTOCHROME P450 2C11; CYTOCHROME P450 2D; CYTOCHROME P450 2E1; CYTOCHROME P450 INHIBITOR; CYTOCHROME REDUCTASE; HYDROXYLAMINE; KETOCONAZOLE; N (2 METHOXYPHENYL)HYDROXYLAMINE; O ANISIDINE; O NITROANISOLE; QUINIDINE; RECOMBINANT ENZYME; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SULFAPHENAZOLE; THIOCTIC ACID; TROLEANDOMYCIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; ENZYME ASSAY; ENZYME METABOLISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIVER MICROSOME; NONHUMAN; PROTEIN ANALYSIS; RAT; TOXICOKINETICS; ULTRAVIOLET SPECTROSCOPY;

EID: 79952791283     PISSN: 0172780X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (51)

1. Balaban AT, Garfield RE, Lesko MJ and Seitz WA (1998). Synthesis and spectral data of some new N-nitroso-N-phenylhydroxyl-amine (cupferron) derivatives. Org Prep Proced Int. 30: 439-446.
2. Beland FA, Fullerton NF, Heflich RH. (1984) Rapid isolation, hydrolysis and chromatography of formaldehyde-modified DNA. J Chromatogr. 308: 121-131. (Pubitemid 14121763)
3. Branner B, Kutzer C, Zwickenpflug W, Scherer G, Heller W-D and Richter E (1998). Haemoglobin adducts from aromatic amines and tobacco-specific nitrosamines in pregnant smoking and non-smoking women. Biomarkers. 3: 35-47. (Pubitemid 28123289)
4. Brennan RJ and Schiestl RH (1997). Aniline and its metabolite generate free radicals in yeast. Mutagenesis. 12: 215-220. (Pubitemid 27331365)
5. Brennan RJ and 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.
6. Cheng G, Shi Y, Sturla S, Jalas J, Mclntee EJ, Villalta PW, et al. (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. (Pubitemid 36245864)
7. Dhareshwar SS and Stella VJ (2008). Your prodrug releases formaldehyde: Should you be concerned? No! J Pharm Sci. 97: 4184-4193.
8. Falter B, Kutzer C and Richter E (1994). Biomonitoring of hemoglobin adducts: aromatic amines and tobacco-specific nitrosamines. Clin Investig. 72: 364-371. (Pubitemid 24171923)
9. Garner RC, Martin CN and 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.
10. Hauthal HG (1993). Rosenmontag und die Folgen die Störfälle der Hoechst AG. Nach. Chem Tech Lab. 41: 440.
11. Huang H and 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.
12. 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.
13. 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.
14. Kim D, Kadlubar FF, Teitel CH and 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. (Pubitemid 38506987)
15. Kirchner G and Bayer U (1992). Genotoxic activity of the aminophenols as evidenced by the induction of sister chromatid exchanges. Hum Toxicol. 1: 387-392.
16. Krizkova J, Burdova K, Hudecek J, Stiborova M and Hodek P (2008). Induction of cytochromes P450 in small intestine by chemopreventive compounds. Neuro Endocrinol Lett. 29: 717-721.
17. Lewis DF (2003). Human cytochromes P450 associated with the phase 1 metabolism of drugs and other xenobiotics: a compilation of substrates and inhibitors of the CYP1, CYP2 and CYP3 families. Curr Med Chem. 10: 1955-1972.
18. 5 profoundly affects hepatic and extra-hepatic drug metabolism. Mol Pharmacol. 78: 269-278.
19. Miksanova M, Novak P, Frei E and Stiborova M (2004). Metabolism of carcinogenic 2-nitroanisole by rat, rabbit, porcine and human hepatic cytosol. Collect Czech Chem Commun. 69: 589-602. (Pubitemid 38526510)
20. Naiman K, Dracinska H, Martinkova M, Sulc M, Dracinsky M, Kejikova L, et al. (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.
21. Naiman K, Hodek P, Liberda J, Schmeiser HH, Frei E and Stiborova M (2010). Rat liver microsomal metabolism of o-aminophenol and N-(2-methoxyphenyl)hydroxylamine, two metabolites of the environmental pollutant and carcinogen o-anisidine in humans. Collect Czech Chem Commun.. 75: 1229-1247.
22. Nedelcheva V and Gut I (1994). P450 in the rat and man: methods of investigation, substrate specificities and relevance to cancer. Xenobiotica. 24: 1151-1175.
23. 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.
24. 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.
25. Okabe N, Fujiwara T, Yamagata Y and Tomita K (1983). Structure of a Potent Antithyroid Drug, 6-Propyl-2-thiouracil. Bull Chem Soc Jpn. 56: 1543-1544. (Pubitemid 14153785)
26. Okhuma Y and 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.
27. Omura T and Sato R (1964). The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem. 239: 2370-2378.
28. 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.
29. Richter E, Rosler S, Scherer G, Gostomzyk JG, Grubl A, Kamer U, et al. (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. (Pubitemid 32780721)
30. Rolsted K and Kissmeyer AM (2008). Evaluation of cytochrome P450 activity in vitro, using dermal and hepatic microsomes from four species and two keratinocyte cell lines in culture. Arch Dermatol Res. 300: 11-18. (Pubitemid 50002031)
31. Rydlova H, Miksanova M, Ryslava H and Stiborova M (2005). Carcinogenic pollutants o-nitroanisole and o-anisidine are substrates and inducers of cytochromes P450. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 49: 441-447.
32. Seidenfaden W (1971). Methoden der Organischen Chemie (Houben-Weyl), Band X/1, Georg Thieme Verlag, Stuttgart, p. 1058.
33. Sistkova J, Hudecek J, Hodek P, Frei E, Schmeiser HH and Stiborova M (2008). Human cytochromes P450 1A1 and 1A2 participate in detoxication of carcinogenic aristolochic acid. Neuro Endocrinol Lett. 29: 733-737.
34. Slepneva IA, Sergeeva SV and Khramtsov VV (1995). Reversible Inhibition of NADPH-cytochrome P450 Reductase by α-lipooic acid. Biochem Biocphys Res Commun. 214: 1246-1253.
35. Sottocasa GL, Kuylenstierna I, Ernster I ad Bergstrand A (1967). An electron transport system associated with the outer membrane of liver mitochondria. J Cell Biol. 32: 415-438.
36. Stabbert R, Schäfer K-H, Biefel C and Rustemeier K (2003). Analysis of aromatic amines in cigarette smoke. Rapid Commun Mass Spectrom. 17: 2125-2132. (Pubitemid 37098328)
37. Stiborova M, Schmeiser HH and 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.
38. 32P-postlabelling analysis of DNA adducts formation. Gen Physiol Biophys. 20: 267-279. (Pubitemid 33040354)
39. Stiborova M, Borek-Dohalska L, Hodek P, Mraz J and Frei E (2002a). New selective inhibitors of cytochromes P450 2B and their application to antimutagenesis of tamoxifen. Arch Biochem Biophys. 403: 41-49. (Pubitemid 34848276)
40. Stiborova M, Miksanova M, Havlicek V, Schmeiser HH and Frei E (2002b). Mechanism of peroxidase-mediated oxidation of carcinogenic o-anisidine and its binding to DNA. Mutat Res. 500: 49-66. (Pubitemid 34219425)
41. 32P-postlabeling. Int J Cancer. 107: 885-890. (Pubitemid 37429828)
42. Stiborova M, Miksanova M, Smrcek S, Bieler CA, Breuer A, Klokow KA, et al. (2004). Identification of a genotoxic mechanism for 2-nitroanisole carcinogenicity and of its carcinogenic potential for humans. Carcinogenesis. 25: 833-840.
43. Stiborova M., Martinek V, Rydlova H, Koblas T and Hodek P (2005a). Expression of cytochrome P450 1A1 and its contribution to oxidation of a potential human carcinogen 1-phenylazo-2-naphthol (Sudan I) in human livers. Cancer Lett. 220: 145-154. (Pubitemid 40568771)
44. Stiborova M, Miksanova M, Sulc M, Rydlova H, Schmeiser HH and Frei E (2005b). Identification of a genotoxic mechanism for the carcinogenicity of the environmental pollutant and suspected human carcinogen o-anisidine. Int J Cancer. 116: 667-678. (Pubitemid 41099697)
45. Strobel HW and Dignam JD (1978). Purification and properties of NADPH-cytochrome P-450 reductase. Methods Enzymol. 52: 89-96.
46. Svobodova M, Martinkova M, Dracinska H, Frei E and Stiborova M (2009). Rat cytochromes P450 oxidize 2-nitrophenol, a human metabolite of carcinogenic 2-nitroanisole. Neuro Endocrinol Lett. 30 (Suppl. 1): 46-51.
47. Traupe H, Menge G, Kandt J and 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. (Pubitemid 27359148)
48. th Report on Carcinogens, U.S. Government Printing Office, Washington, DC.
49. Weiss T and 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.
50. Wiechelman KJ, Braun RD and Fitzpatrick JD (1988). Investigation of the bicinchoninic acid protein assay: identification of the groups responsible for color formation. Anal Biochem. 175: 231-237.
51. 5 or heme oxygenase. J Biol Chem. 276: 30885-30891.