Enzymes involved in the metabolism of the carcinogen 2-Nitroanisole: Evidence for its oxidative detoxication by human cytochromes P450

Chemical Research in Toxicology

Volumn 17, Issue 5, 2004, Pages 663-671

  Mikšanová, Markéta ^a   Šulc, Miroslav ^a   Rýdlová, Helena ^a   Schmeiser, Heinz H ^b   Frei, Eva ^b   Stiborová, Marie ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

^b GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 NITROANISOLE; 2 NITROPHENOL; AROMATIC NITRO COMPOUND; CYTOCHROME P450; CYTOCHROME P450 1A1; CYTOCHROME P450 2B6; CYTOCHROME P450 2E1; NITROBENZENE; PHOSPHORUS 32; UNCLASSIFIED DRUG;

AEROBIC METABOLISM; ANIMAL CELL; ARTICLE; BACULOVIRUS; BIOTRANSFORMATION; CARCINOGENICITY; CONTROLLED STUDY; CORRELATION COEFFICIENT; COVALENT BOND; DEMETHYLATION; DETOXIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; INSECT CELL; LIVER MICROSOME; MASS SPECTROMETRY; NONHUMAN; POLLUTANT; RABBIT; RAT;

ANIMALS; ANISOLES; CARCINOGENS; CELL LINE; CELL MEMBRANE; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; METABOLIC DETOXICATION, DRUG; MICROSOMES, LIVER; OXIDATION-REDUCTION; RABBITS; RECOMBINANT PROTEINS; TIME FACTORS; TRANSFECTION;

ANIMALIA; INSECTA; ORYCTOLAGUS CUNICULUS; RODENTIA; UNIDENTIFIED BACULOVIRUS;

EID: 2442696549     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0499721     Document Type: Article

References (64)

1. Garner, R. C., Martin, C. N., and Clayson, D. B. (1984) Carcinogenic aromatic amines and related compounds. In Chemical Carcinogens, 2nd ed. (Searle, C., Ed.) ACS Monograph 182, Vol. 1, pp 175-302, American Chemical Society, Washington, DC.
2. International Agency for Research in Cancer (IARC) (1989) Diesel and Gasoline Engine Exhausts and Some Nitroarenes, No. 46, IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Lyon.
3. Purohit, V., and Basu, A. (2000) Mutagenicity of nitroaromatic compounds. Chem. Res. Toxicol. 13, 673-692.
4. Sabbioni, G., and Jones, C. R. (2002) Biomonitoring arylamines and nitroarenes. Biomarkers 7, 347-421.
5. El-Bayoumy, K., Desai, D., Boyiri, T., Rosa, J., Krzeminski, J., Sharma, A. K., Pittman, B., and Amin, S. (2002) Comparative tumorigenicity of the environmental pollutant 6-nitrochrysene and its metabolites in the rat mammary gland. Chem. Res. Toxicol. 15, 972-978.
6. Cui, X. S., Bergman, J., and Moller, L. (1996) Preneoplastic lesions, DNA adduct formation and mutagenicity of 5-, 7- and 9-hydroxy-2-nitrofluorene, metabolites of the air pollutant 2-nitrofluorene. Mutat. Res. 369, 147-155.
7. Ritter, C. L., Culp, S. J., Freeman, J. P., Marques, M. M., Beland, F. A., and Malejka-Giganti, D. (2002) DNA adducts from nitroreduction of 2,7-dinitrofluorene, a mammary gland carcinogen, catalyzed by rat liver or mammary gland cytosol. Chem. Res. Toxicol. 15, 536-544.
8. Cui, X. S., Eriksson, L. C., and Moller, L. (1999) Formation and persistence of DNA adducts during and after a long-term administration of 2-nitrofluorene. Mutat. Res. 442, 9-18.
9. Ritter, C. L., Decker, R. W., and Malejka-Giganti, D. (2000) Reduction of nitro and 9-oxo groups of environmental nitrofluorenes by the rat mammary gland in vitro. Chem. Res. Toxicol. 13, 793-800.
10. Anonymous (1993) Toxicology and Carcinogenesis. Studies of o-Nitroanisole, No. 416, NTP Technical Report, National Institute of Health, U.S. Department of Health and Human Services Bethesda, MD.
11. Anonymous (1978) Bioassay of o-Anisidine Hydrochloride for Possible Carcinogenicity, NTP Technical Report 89, National Institute of Health, U.S. Department of Health and Human Services, Bethesda, MD.
12. Traupe, H., Menge, G., Kandt, I., 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.
13. Hengstler, J. G., Fuchs, J., Bolmaudorff, U., Meyer, S., and Oesch, F. (1995) Single-strand breaks in deoxyribonucleic acid in fire fighters accidentally exposed to o-nitroanisole and other chemicals. Scand. J. Work Environ. Health 21, 36-42.
14. Fu, P. P. (1990) Metabolism of nitro-polycyclic aromatic hydrocarbons. Drug Metab. Rev. 22, 209-268.
15. Bieler, C. A., Wiessler, M., Erdinger, L., Suzuki, H., Enya, T., and Schmeiser, H. H. (1999) DNA adduct formation from the mutagenic air pollutant 3-nitrobenzanthrone. Mutat. Res. 439, 307-311.
16. Stiborová, M., Frei, E., Wiessler, M., and Schmeiser, H. H. (2001) Human enzymes involved in metabolic activation of carcinogenic aristolochic acids: evidence for reductive activation by cytochromes P450 1A1 and 1A2. Chem. Res. Toxicol. 14, 1128-1137.
17. Stiborová, M., Frei, E., Sopko, B., Wiessler, M., and Schmeiser, H. H. (2002) Carcinogenic aristolochic acids upon activation by DT-diaphorase form adducts found in DNA of patients with Chinese herbs nephropathy. Carcinogenesis 23, 617-625.
18. Arlt, V. M., Stiborová, M., Hewer, A., Schmeiser, H. H., and Phillips, D. H. (2003) Human enzymes involved in the metabolic activation of the environmental contaminant 3-nitrobenzanthrone: evidence for reductive activation by human NADPH: cytochrome P450. Cancer Res. 63, 2752-2761.
19. Stiborová, M., Frei, E., Sopko, B., Sopková, K., Marková, V., Lafiková, M., Kumstýřová, T., Wiessler, M., and Schmeiser, H. H. (2003) Human cytosolic enzymes involved in the metabolic activation of carcinogenic aristolochic acid: evidence for reductive activation by human NAD(P)H: quinone oxidoreductase. Carcinogenesis 24, 1695-1703.
20. Hein, D. W., Doll, M. A., Fretland, A. J., Gray, K., Deitz, A. C., Feng, Y., Jiang, W., Rustan, T. D., Satran, S., and Wilkie, T. R. (1997) Rodent models of the human acetylation polymorphism: comparison of recombinant acetyltransferases. Mutat. Res. 376, 101-106.
21. Glatt, H. (2000) Sulfotransferases in the bioactivation of xenobiotics. Chem.-Biol. Interact. 129, 141-170.
22. Arlt, V. M., Glatt, H., Muckel, E., Pabel, U., Sorg, B. L., Schmeiser, H. H., and Phillips, D. H. (2002) Metabolic activation of the environmental contaminant 3-nitrobenzanthrone by human acetyl-transferases and sulfotransferase. Carcinogenesis 23, 1937-1945.
23. Arlt, V. M., Glatt, H., Muckel, E., Pabel, U., Sorg, B. L., Seidel, A., Frank, H., Schmeiser, H. H., and Phillips, D. H. (2003) 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.
24. Miller, M. J., Sipes, I. G., Perry, D. F., and Carter, D. E. (1985) Pharmacokinetics of o-nitroanisole in Fischer 344 rats. Drug Metab. Dispos. 13, 527-531.
25. Stiborová, M., Mikšanová, M., Schmeiser, H. H., Wiessler, M., and Frei, E. (2001) Towards the explanation of the carcinogenicity of 2-nitroanisole and 2-anisidine, carcinogens with unknown mechanism. J. Cancer Res. Clin. Oncol. 127, S31.
26. Stiborová, M., Schmeiser, H. H., 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.
27. Mikšanová, M., Novák, P., Frei, E., and Stiborová, M. (2004) Metabolism of carcinogenic 2-nitroanisole by rat, rabbit, porcine and human hepatic cytosol. Collect. Czech. Chem. Commun. 69, 589-602.
28. Stiborová, M., Mikšanová, M., Smrček, S., Bieler, C. A., Breuer, A., Klokow, K. A., Schmeiser, H. H., and Frei, E. (2004) Identification of a genotoxic mechanism for 2-nitroanisole carcinogenicity and of its carcinogenic potential for humans. Carcinogenesis 25, in press.
29. Olah, G. A., Wu, A., Farooq, O., and Prakash, G. K. S. (1990) Synthetic methods and reactions. 146. Olefins from crowded carbonyl-compounds with tert-butyllithium (tert-butylmangnesium chloride) thionyl chloride-study of carbocationic reaction intermediates and rearrangement cleavage under stable ion conditions using C-13 NMR-spectroscopy. J. Org. Chem. 55, 1792-1796.
30. Sakaue, S., Tsubakino, T., Nishiyama, Y., and Ishii, Y. (1993) Oxidation of aromatic-amines with hydroge-peroxide catalyzed by cetylpyridinium heteropolyoxometalates. J. Org. Chem. 58, 3633-3638.
31. Schmeiser, H. H., Bieler, C. A., Wiessler, M., van Ypersele de Strihou, C., and Cosyns, J.-P. (1996) Detection of DNA adducts formed by aristolochic acid in renal tissue from patients with Chinese herbs nephropathy. Cancer Res. 56, 2025-2028.
32. 32P-post-labeling: evidence for reductive activation by peroxidases. Carcinogenesis 18, 1055-1062.
33. Stiborová, M., Bořek-Dohalská, L., Hodek, P., Mráz, J., and Frei, E. (2002) New selective inhibitors of cytochromes P450 2B and their application to antimutagenesis of tamoxifen. Arch. Biochem. Biophys. 403, 41-49.
34. Stiborová, M., Asfaw, B., Frei, E., Schmeiser, H. H., and Wiessler, M. (1995) Benzenediazonium ion derived from Sudan I forms an 8-(phenylazo)guanine adduct. Chem. Res. Toxicol. 8, 489-498.
35. Wiechelman, K. J., Braun, R. D., and Fitzpatrick, J. D. (1988) Investigation of the bicinchoninic acid protein assay: identification of the groups responsible for color formation. Anal. Biochem. 175, 231-237.
36. 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.
37. Haugen, D. A., and Coon, M. J. (1976) Properties of electrophoretically homogeneous phenobarbital-inducible and beta-naphthoflavone-inducible forms of liver microsomal cytochrome P-450. J. Biol. Chem. 251, 7929-7939.
38. Yang, C. S., Tu, Y. Y., Koop, D. R., and Coon, M. J. (1985) Metabolism of nitrosamines by purified rabbit liver cytochrome P-450 isozymes. Cancer Res. 45, 1140-1145.
39. Bořek-Dohalská, L., Hodek, P., Šulc, M., and Stiborová, M. (2001) (x-Naphthoflavone acts as activator and reversible or irreversible inhibitor of rabbit microsomal P4503A6. Chem.-Biol. Interact. 138, 85-106.
40. Saito, T., and Strobel, H. W. (1981) Purification to homogeneity and characterization of a form of cytochrome P-450 with high specificity for benzo[a]pyrene from β-naphthoflavone-pretreated rat liver microsomes. J. Biol. Chem. 256, 984-988.
41. Yasukochi, Y., Peterson, J. A., and Masters, B. (1979) NADPH-cytochrome c (P450) reductase: spectrophotometric and stopped flow kinetic studies on the formation of reduced flavoprotein intermediates. J. Biol. Chem. 254, 7097-7104.
42. 5. Methods Enzymol. 52, 97-101.
43. Burke, M. D., Thompsom, S., Elcombe, O. R., Halpert, J., Haaparanta, T., and Mayer, R. T. (1985) Ethoxy-, penthoxy- and benzyloxyphenazones and homologues: A series of substrates to distinguish between different induced cytochromes P-450. Biochem. Pharmacol. 34, 3337-3345.
44. 5 or heme oxygenase. J. Biol. Chem. 276, 30885-30891.
45. Lubet, R. A., Mayer, R. T., Cameron, J. W., Nims, R. W., Burke, M. D., Wolff, T., and Guengerich, F. P. (1985) Dealkylation of penthoxyresorufin: a rapid and sensitive assay for measuring induction of cytochrome(s) P-450 by Phenobarbital and other xenobiotics in the rat. Arch. Biochem. Biophys. 238, 43-48.
46. Guengerich, F. P. (1991) Oxidation of toxic and carcinogenic chemicals by human cytochrome P450 enzymes. Chem. Res. Toxicol. 4, 391-407.
47. Cleland, W. W. (1983) Statistical analysis of the enzyme kinetic data. Methods Enzymol. 63, 103-138.
48. Boř-Dohalská, L., Hodek, P., and Stiborová, M. (1999) New selective inhibitors of cytochrome P450 2B4 and an activator of cytochrome P450 3A6 in rabbit liver microsomes. Collect. Czech. Chem. Commun. 65, 122-132.
49. 32P-postlabeling analysis of DNA adduct formation. Mutat. Res. 493, 153-164.
50. Yamazoe, Y., Zenser, T. V., Miller, D. W., and Kadlubar, F. F. (1988) Mechanism of formation and structural characterization of DNA adducts derived from peroxidative activation of benzidine. Carcinogenesis 9, 1635-1641.
51. 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis 7, 1543-1551.
52. 32P-adduct assay comparative recoveries of structurally diverse DNA adducts in the various enhancement procedures. Carcinogenesis 8, 1687-1693.
53. Stiborová, M., Mikšanová, M., Havlíč ek, V., Schmeiser, H. H., and Frei, E. (2002) Mechanism of peroxidase-mediated oxidation of carcinogenic o-anisidine and its binding to DNA. Mutat. Res. 500, 49-66.
54. Reddy, M. V., Bleicher, W. T., Blackburn, G. R., and Mackerer, E. R. (1990) DNA adduction by phenol, hydroquinone, or benzpquinone in vitro but not in vivo. Carcinogenesis 8, 1349-1357.
55. Burgschat, H., and Netter, K. J. (1977) Applucation of A. C. -polarography in a study of p-nitroanisole metabolism and its kinetic properties. J. Pharmacol. Exp. Ther. 201, 482-489.
56. Gelboin, V., Goldfarb, I., Krausz, K. W., Grogan, J., Korzekwa, K. R., Gonzalez, F. J., and Shou, M. (1996) Inhibitory and noninhibitory monoclonal antibodies to human cytochrome P450 2E1. Chem. Res. Toxicol. 9, 1023-1030.
57. Rendic, S., and DiCarlo, F. J. (1997) Human cytochrome P450 enzymes: A status report summarizing their reactions, substrates, inducers, and inhibitors. Drug Metab. Rev. 29, 413-480.
58. Schneider, T., Frei, E., and Wiessler, M. (1999) The profile of urinary metabolites of 4-(methylnitrosamino)-1-)3-pyridyl)-1-butanone in rats is determined by its pulmonary metabolism. Chem.-Biol. Interact. 118, 247-266.
59. Gonzalez, F. J. (1992) Human cytochrome P450: problems and prospects. TiPS 13, 346-352.
60. Mace, K., Bowman, E. D., Vautravers, P., Shields, P. G., Harris, C. C., and Pfeifer, A. M. A. (1998) Characterisation of xenobiotic-metabolising enzyme expression in human bronchial mucosa and peripheral lung tissue. Eur. J. Cancer 34, 914-920.
61. Landi, M. T., Sinha, R., Lang, N. P., and Kadlubar, F. F. (1999) Human cytochrome P4501A2. In Metabolic Polymorphisms and Susceptibility to Cancer, No. 148 (Vineis, P., Malats, N., Lang, M., d'Errico, A., Caporaso, N., Cuzick, J., and Boffetta P., Eds.) pp 173-195, International Agency for Research on Cancer, IARC Sci. Publ., Lyon.
62. Guengerich, F. P., Parikh, A., Turesky, R. J., and Josephy, P. D. (1999) Inter-individual differences in the metabolism of environmental toxicants: cytochrome P450 1A2 as a prototype. Mutat. Res. 428, 115-124.
63. Kato, S., Shields, P. G., Caporaso, N. E., Sugimura, H., Trievers, G. E., Tucker, M. A, Trump, B. F., and Weston, A. (1994) Analysis of cytochrome P450 2E1 genetic polymorphisms in relation to human lung cancer. Cancer. Epidemiol. Biomarkers Prev. 3, 515-518.
64. Perera, F. P. (1997) Environment and Cancer: Who are susceptible? Science 278, 1068-1073.