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Volumn 17, Issue 9, 1996, Pages 2029-2034

Cytochrome P450 metabolic dealkylation of nine N-nitrosodialkylamines by human liver microsomes

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROPHENOL; ALIPHATIC AMINE; CARCINOGEN; CHLORZOXAZONE; COUMARIN; CYTOCHROME P450; DIBUTYLNITROSAMINE; DIETHYLNITROSAMINE; DIMETHYLNITROSAMINE; DIPROPYLNITROSAMINE; MEPHENYTOIN; NIFEDIPINE; TOLBUTAMIDE;

EID: 0029814521     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/17.9.2029     Document Type: Article
Times cited : (62)

References (31)
  • 1
    • 9044254525 scopus 로고    scopus 로고
    • P450 superfamily: Update on new sequences, gene mapping, accession numbers and nomenclature
    • Nelson, D.R. et al. (1996) P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics, 12, 1-51.
    • (1996) Pharmacogenetics , vol.12 , pp. 1-51
    • Nelson, D.R.1
  • 2
    • 0027178457 scopus 로고
    • Hydroxylation and dealkylation of methyl-n-butylnitrosamine and role of certain cytochrome P-450 isozymes in these reactions
    • Huang, Q., Wang, S., Chen, S.C., Babcook, D.M., Park, S.S., Gelboin, H.V. and Mirvish, S.S. (1993) Hydroxylation and dealkylation of methyl-n-butylnitrosamine and role of certain cytochrome P-450 isozymes in these reactions. Cancer Lett., 69, 107-116.
    • (1993) Cancer Lett. , vol.69 , pp. 107-116
    • Huang, Q.1    Wang, S.2    Chen, S.C.3    Babcook, D.M.4    Park, S.S.5    Gelboin, H.V.6    Mirvish, S.S.7
  • 3
    • 0024514295 scopus 로고
    • Substrate specificity and alkyl group selectivity in the metabolism of N-nitrosodialkylamines
    • Lee, M., Ishizaki, H., Brady, J.F. and Yang, C.S. (1989) Substrate specificity and alkyl group selectivity in the metabolism of N-nitrosodialkylamines. Cancer Res., 49, 1470-1474.
    • (1989) Cancer Res. , vol.49 , pp. 1470-1474
    • Lee, M.1    Ishizaki, H.2    Brady, J.F.3    Yang, C.S.4
  • 4
    • 0026593478 scopus 로고
    • N-Nitrosodialkylamine dealkylation in reconstituted systems containing cytochrome P-450 purified from phenobarbital and β-naphthoflavone treated rats
    • Kawanishi, T., Ohno, Y., Takanaka, A., Kawano, S., Yamazoe, Y., Kato, R. and Omori, Y. (1992) N-Nitrosodialkylamine dealkylation in reconstituted systems containing cytochrome P-450 purified from phenobarbital and β-naphthoflavone treated rats. Arch. Toxicol., 66, 137-142.
    • (1992) Arch. Toxicol. , vol.66 , pp. 137-142
    • Kawanishi, T.1    Ohno, Y.2    Takanaka, A.3    Kawano, S.4    Yamazoe, Y.5    Kato, R.6    Omori, Y.7
  • 5
    • 0023877321 scopus 로고
    • Metabolism of N-nitrosodialkylamines by human liver microsomes
    • Yoo, J.S.H., Guengerich, F.P. and Yang, C.S. (1988) Metabolism of N-nitrosodialkylamines by human liver microsomes. Cancer Res., 88, 1499-1504.
    • (1988) Cancer Res. , vol.88 , pp. 1499-1504
    • Yoo, J.S.H.1    Guengerich, F.P.2    Yang, C.S.3
  • 6
    • 0027270458 scopus 로고
    • High variability of metabolism among individuals: Role of cytochromes P450 2A6 and 2E1 in the dealkylation of N-nitrosodimethylamine and N-nitrosodiethylamine in mice and humans
    • Camus, A.M., Geneste, O., Honkakoski, P., Béréziat, J.C., Henderson, C.J., Wolf, C.R., Bartsch, H. and Lang, M.A. (1993) High variability of metabolism among individuals: role of cytochromes P450 2A6 and 2E1 in the dealkylation of N-nitrosodimethylamine and N-nitrosodiethylamine in mice and humans. Mol. Carcinogen., 7, 268-275.
    • (1993) Mol. Carcinogen. , vol.7 , pp. 268-275
    • Camus, A.M.1    Geneste, O.2    Honkakoski, P.3    Béréziat, J.C.4    Henderson, C.J.5    Wolf, C.R.6    Bartsch, H.7    Lang, M.A.8
  • 7
    • 0026744568 scopus 로고
    • Cytochrome P450 2E1 and 2A6 enzymes as major catalysts for metabolic activation of N-nitrosodialkylamines and tobacco-related nitrosamines in human liver microsomes
    • Yamazaki, H., Inui, Y., Yun, C.H., Guengerich, F.P. and Shimada, T. (1992) Cytochrome P450 2E1 and 2A6 enzymes as major catalysts for metabolic activation of N-nitrosodialkylamines and tobacco-related nitrosamines in human liver microsomes. Carcinogenesis, 13, 1789-1794.
    • (1992) Carcinogenesis , vol.13 , pp. 1789-1794
    • Yamazaki, H.1    Inui, Y.2    Yun, C.H.3    Guengerich, F.P.4    Shimada, T.5
  • 8
    • 0025992864 scopus 로고
    • Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes
    • Guengerich, F.P. and Shimada, T. (1991) Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes. Chem. Res. Toxicol., 4, 391-407.
    • (1991) Chem. Res. Toxicol. , vol.4 , pp. 391-407
    • Guengerich, F.P.1    Shimada, T.2
  • 9
    • 0026035519 scopus 로고
    • Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects
    • Guengerich, F.P., Kim, D.H. and Iwasaki, M. (1991) Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects. Chem. Res. Toxicol., 4, 168-179.
    • (1991) Chem. Res. Toxicol. , vol.4 , pp. 168-179
    • Guengerich, F.P.1    Kim, D.H.2    Iwasaki, M.3
  • 10
    • 0022827585 scopus 로고
    • Ethanol oxidation and toxicity: Role of alcohol P-450 oxygenase
    • Koop, D.R. and Coon, M.J. (1986) Ethanol oxidation and toxicity: role of alcohol P-450 oxygenase. Alcohol Clin. Exp. Res., 10, 445-495.
    • (1986) Alcohol Clin. Exp. Res. , vol.10 , pp. 445-495
    • Koop, D.R.1    Coon, M.J.2
  • 11
    • 0026082836 scopus 로고
    • cDNA-expressed human cytochrome P450s: A new age of molecular toxicology and human risk assessment
    • Gonzalez, F.J., Crespi, C.L. and Gelboin, H.V. (1991) cDNA-expressed human cytochrome P450s: a new age of molecular toxicology and human risk assessment. Mutat. Res., 247, 113-127.
    • (1991) Mutat. Res. , vol.247 , pp. 113-127
    • Gonzalez, F.J.1    Crespi, C.L.2    Gelboin, H.V.3
  • 12
    • 0021806780 scopus 로고
    • Immunochemical evidence for induction of the alcohol-oxidizing cytochrome P450 of rabbit liver microsomes by diverse agents: Ethanol, imidazole, trichlorethylene, acetone, pyrazole and isoniazid
    • Koop, D., Crump, B.L., Nordblom, G.D. and Coon, M.J. (1985) Immunochemical evidence for induction of the alcohol-oxidizing cytochrome P450 of rabbit liver microsomes by diverse agents: ethanol, imidazole, trichlorethylene, acetone, pyrazole and isoniazid. Proc. Natl Acad. Sci. USA, 82, 4065-4069.
    • (1985) Proc. Natl Acad. Sci. USA , vol.82 , pp. 4065-4069
    • Koop, D.1    Crump, B.L.2    Nordblom, G.D.3    Coon, M.J.4
  • 13
    • 0024506260 scopus 로고
    • Comparison of caffeine metabolism by slices, microsomes and hepatocyte cultures from adult human liver
    • Berthou, F., Ratanasavanh, D., Riché, C., Picart, D., Voirin, T. and Guillouzo, A. (1989) Comparison of caffeine metabolism by slices, microsomes and hepatocyte cultures from adult human liver. Xenobiotica, 19, 401-417.
    • (1989) Xenobiotica , vol.19 , pp. 401-417
    • Berthou, F.1    Ratanasavanh, D.2    Riché, C.3    Picart, D.4    Voirin, T.5    Guillouzo, A.6
  • 14
    • 0028232498 scopus 로고
    • Involvement of cytochrome P450 3A enzyme family in the major metabolic pathways of toremifene in human liver microsomes
    • Berthou, F., Dréano, Y., Belloc, C., Kangas, L., Gautier, J.C. and Beaune, P. (1994) Involvement of cytochrome P450 3A enzyme family in the major metabolic pathways of toremifene in human liver microsomes. Biochem. Pharmacol., 47, 1883-1895.
    • (1994) Biochem. Pharmacol. , vol.47 , pp. 1883-1895
    • Berthou, F.1    Dréano, Y.2    Belloc, C.3    Kangas, L.4    Gautier, J.C.5    Beaune, P.6
  • 15
    • 0023060630 scopus 로고
    • Determination of free acetaldehyde in blood as the dinitrophenylhydrazone derivative by high-performance liquid chromatography
    • Lucas, D., Ménez, J.F., Berthou, F., Pennec, Y. and Floch, H.H. (1986) Determination of free acetaldehyde in blood as the dinitrophenylhydrazone derivative by high-performance liquid chromatography. J. Chromatogr., 382, 57-66.
    • (1986) J. Chromatogr. , vol.382 , pp. 57-66
    • Lucas, D.1    Ménez, J.F.2    Berthou, F.3    Pennec, Y.4    Floch, H.H.5
  • 16
    • 0028106482 scopus 로고
    • Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat
    • Burke, M.D., Thompson, S., Weaver, R.J., Wolf, C.R. and Mayer, R.T. (1994) Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat. Biochem. Pharmacol., 48, 923-936.
    • (1994) Biochem. Pharmacol. , vol.48 , pp. 923-936
    • Burke, M.D.1    Thompson, S.2    Weaver, R.J.3    Wolf, C.R.4    Mayer, R.T.5
  • 17
    • 0025014594 scopus 로고
    • Tolbutamide and mephenytoin hydroxylation by human cytochrome P450s in the CYP 2C subfamily
    • Relling, M.V., Aoyama, T., Gonzalez, F.J. and Meyer, U.A. (1990) Tolbutamide and mephenytoin hydroxylation by human cytochrome P450s in the CYP 2C subfamily. J. Pharmacol. Exp. Ther., 252, 442-447.
    • (1990) J. Pharmacol. Exp. Ther. , vol.252 , pp. 442-447
    • Relling, M.V.1    Aoyama, T.2    Gonzalez, F.J.3    Meyer, U.A.4
  • 18
    • 0027265750 scopus 로고
    • P450 2D6 and P450 3A-dependent metabolism of dextromethorphan in humans
    • Jacqz-Aigrin, C., Funck-Brentano, C. and Cresteil, T. (1993) P450 2D6 and P450 3A-dependent metabolism of dextromethorphan in humans. Pharmacogenetics, 3, 197-204.
    • (1993) Pharmacogenetics , vol.3 , pp. 197-204
    • Jacqz-Aigrin, C.1    Funck-Brentano, C.2    Cresteil, T.3
  • 20
    • 0027253618 scopus 로고
    • HPLC assay for 4-nitrophenol hydroxylation, a putative cytochrome P-450 2E1 activity, in human liver microsomes
    • Tassaneeyakul, W., Veronese, M.E., Birkett, D.J. and Miners, J.O. (1993) HPLC assay for 4-nitrophenol hydroxylation, a putative cytochrome P-450 2E1 activity, in human liver microsomes. J. Chromatogr., 616, 73-78.
    • (1993) J. Chromatogr. , vol.616 , pp. 73-78
    • Tassaneeyakul, W.1    Veronese, M.E.2    Birkett, D.J.3    Miners, J.O.4
  • 21
    • 0022998708 scopus 로고
    • Characterization of rat and human liver microsomal cytochrome P450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism
    • Guengerich, F.P., Martin, M.V., Beaune, P.H., Kremers, F., Wolff, T. and Waxman, D.J. (1986) Characterization of rat and human liver microsomal cytochrome P450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism. J. Biol. Chem., 261, 5051-5060.
    • (1986) J. Biol. Chem. , vol.261 , pp. 5051-5060
    • Guengerich, F.P.1    Martin, M.V.2    Beaune, P.H.3    Kremers, F.4    Wolff, T.5    Waxman, D.J.6
  • 22
    • 0013794926 scopus 로고
    • A spectrofluorimetric study of the 7-hydroxylation of coumarin by liver microsomes
    • Creaven, P.J., Parke, D.V. and Williams, R.T. (1965) A spectrofluorimetric study of the 7-hydroxylation of coumarin by liver microsomes. Biochem. J., 96, 390-398.
    • (1965) Biochem. J. , vol.96 , pp. 390-398
    • Creaven, P.J.1    Parke, D.V.2    Williams, R.T.3
  • 23
    • 0029071838 scopus 로고
    • Role of N-nitroso compounds (NOC) and N-nitrosation in etiology of gastric esophageal, nasopharyngeal and bladder cancer and contribution to cancer of known exposures to NOC
    • Mirvish, S.S. (1995) Role of N-nitroso compounds (NOC) and N-nitrosation in etiology of gastric esophageal, nasopharyngeal and bladder cancer and contribution to cancer of known exposures to NOC. Cancer Lett., 93, 17-48
    • (1995) Cancer Lett. , vol.93 , pp. 17-48
    • Mirvish, S.S.1
  • 24
    • 0021680014 scopus 로고
    • Relevance of nitrosamines to human cancer
    • Bartsh, H. and Montesano, R. (1984) Relevance of nitrosamines to human cancer. Carcinogenesis, 5, 1381-1393.
    • (1984) Carcinogenesis , vol.5 , pp. 1381-1393
    • Bartsh, H.1    Montesano, R.2
  • 25
    • 0025635625 scopus 로고
    • Roles of cytochrome P450 IIE1 in the dealkylation and denitrosation of N-nitrosodimethylamine and N-nitrosodiethylamine in rat liver microsomes
    • Yoo, J.S.H., Ishizaki, H. and Yang, C.S. (1990) Roles of cytochrome P450 IIE1 in the dealkylation and denitrosation of N-nitrosodimethylamine and N-nitrosodiethylamine in rat liver microsomes. Carcinogenesis, 11, 2239-2243.
    • (1990) Carcinogenesis , vol.11 , pp. 2239-2243
    • Yoo, J.S.H.1    Ishizaki, H.2    Yang, C.S.3
  • 26
    • 0025757011 scopus 로고
    • Comparison of levels of several human microsomal cytochrome P450 enzyme and epoxide hydrolase in normal and disease states using immunochemical analysis of surgical liver samples
    • Guengerich, F.P. and Turvy, C.G. (1991) Comparison of levels of several human microsomal cytochrome P450 enzyme and epoxide hydrolase in normal and disease states using immunochemical analysis of surgical liver samples. J. Pharmacol. Exp. Ther., 256, 1189-1194.
    • (1991) J. Pharmacol. Exp. Ther. , vol.256 , pp. 1189-1194
    • Guengerich, F.P.1    Turvy, C.G.2
  • 27
    • 0028237729 scopus 로고
    • Interindividual variation in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: Studies with liver microsomes of 30 Japanese and 30 Caucasians
    • Shimada, T., Minara, M., Inui, Y. and Guengerich, F.P. (1994) Interindividual variation in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. J. Pharmacol. Exp. Ther., 270, 414-423.
    • (1994) J. Pharmacol. Exp. Ther. , vol.270 , pp. 414-423
    • Shimada, T.1    Minara, M.2    Inui, Y.3    Guengerich, F.P.4
  • 28
    • 0025022689 scopus 로고
    • The CYP2A3 gene product catalyses coumarin 7-hydroxylation in human liver microsomes
    • Yamano, S., Tatsuno, J. and Gonzalez, F.J. (1990) The CYP2A3 gene product catalyses coumarin 7-hydroxylation in human liver microsomes. Biochemisty, 29, 1322-1329.
    • (1990) Biochemisty , vol.29 , pp. 1322-1329
    • Yamano, S.1    Tatsuno, J.2    Gonzalez, F.J.3
  • 29
    • 0030024786 scopus 로고    scopus 로고
    • Effect of the length of alkyl chain on the cytochrome P450 dependent metabolism of N-dialkylnitrosamines
    • Bellec, G., Goasduff, T., Dréano, Y., Ménez, J.F. and Berthou, F. (1996) Effect of the length of alkyl chain on the cytochrome P450 dependent metabolism of N-dialkylnitrosamines. Cancer Lett., 100, 115-123.
    • (1996) Cancer Lett. , vol.100 , pp. 115-123
    • Bellec, G.1    Goasduff, T.2    Dréano, Y.3    Ménez, J.F.4    Berthou, F.5
  • 30
    • 0028954947 scopus 로고
    • Probing the active sites of rat and human cytochrome P450 2E1 with alcohols and carboxylic acids
    • Wang, M.H., Wade, D., Chen, L., White, S. and Yang, C.S. (1995) Probing the active sites of rat and human cytochrome P450 2E1 with alcohols and carboxylic acids. Arch. Biochem. Biophys., 317, 299-304.
    • (1995) Arch. Biochem. Biophys. , vol.317 , pp. 299-304
    • Wang, M.H.1    Wade, D.2    Chen, L.3    White, S.4    Yang, C.S.5
  • 31
    • 0030034986 scopus 로고    scopus 로고
    • Active site topology of human cytochrome P450 2E1
    • Ortiz de Montanello, P. (1996) Active site topology of human cytochrome P450 2E1. Chem. Res. Toxicol., 9, 223-226.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 223-226
    • Ortiz De Montanello, P.1


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