메뉴 건너뛰기




Volumn 37, Issue 3, 2009, Pages 665-671

Effect of CYP2A13 active site mutation N297A on metabolism of coumarin and tobacco-specific nitrosamines

Author keywords

[No Author keywords available]

Indexed keywords

4 (METHYLNITROSAMINO) 1 (3 PYRIDYL) 1 BUTANONE; COUMARIN; CYTOCHROME P450 2A13; CYTOCHROME P450 ISOENZYME; NITROSONORNICOTINE; UNCLASSIFIED DRUG;

EID: 61449158840     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.108.025072     Document Type: Article
Times cited : (18)

References (26)
  • 2
    • 28144440301 scopus 로고    scopus 로고
    • Nicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-butanone (NNK) metabolism by P450 2B6
    • Dicke KE, Skrlin SM, and Murphy SE (2005) Nicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-butanone (NNK) metabolism by P450 2B6. Drug Metab Dispos 33:1760-1764.
    • (2005) Drug Metab Dispos , vol.33 , pp. 1760-1764
    • Dicke, K.E.1    Skrlin, S.M.2    Murphy, S.E.3
  • 3
    • 0031822496 scopus 로고    scopus 로고
    • Role of the alanine at position 363 of cytochrome P450 2B2 in influencing the NADPH- and hydroperoxide-supported activities
    • Hanna IH, Teiber JF, Kokones KL, and Hollenberg PF (1998) Role of the alanine at position 363 of cytochrome P450 2B2 in influencing the NADPH- and hydroperoxide-supported activities. Arch Biochem Biophys 350:324-332.
    • (1998) Arch Biochem Biophys , vol.350 , pp. 324-332
    • Hanna, I.H.1    Teiber, J.F.2    Kokones, K.L.3    Hollenberg, P.F.4
  • 4
    • 0031831381 scopus 로고    scopus 로고
    • Biochemistry, biology, and carcinogenicity of tobacco-specific N-nitrosamines
    • Hecht SS (1998) Biochemistry, biology, and carcinogenicity of tobacco-specific N-nitrosamines. Chem Res Toxicol 11:559-603.
    • (1998) Chem Res Toxicol , vol.11 , pp. 559-603
    • Hecht, S.S.1
  • 5
    • 0031427202 scopus 로고    scopus 로고
    • The structure, function, and regulation of cytochrome P450 2A enzymes
    • Honkakoski P and Negishi M (1997) The structure, function, and regulation of cytochrome P450 2A enzymes. Drug Metab Rev 29:977-996.
    • (1997) Drug Metab Rev , vol.29 , pp. 977-996
    • Honkakoski, P.1    Negishi, M.2
  • 6
    • 66049101105 scopus 로고    scopus 로고
    • Smokeless tobacco and tobacco-specific nitrosamines
    • International Agency for Research on Cancer , International Agency for Research on Cancer, Lyon, France
    • International Agency for Research on Cancer (2007) Smokeless tobacco and tobacco-specific nitrosamines, in IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, vol 89, pp 564, International Agency for Research on Cancer, Lyon, France.
    • (2007) IARC Monographs on the Evaluation of Carcinogenic Risks to Humans , vol.89 , pp. 564
  • 7
    • 0141792916 scopus 로고    scopus 로고
    • Comparative metabolism of the tobacco-specific nitrosamines 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) by rat cytochrome P450 2A3 and human cytochrome P450 2A13
    • Jalas JR, Ding X, and Murphy SE (2003) Comparative metabolism of the tobacco-specific nitrosamines 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) by rat cytochrome P450 2A3 and human cytochrome P450 2A13. Drug Metab Dispos 31:1199-1202.
    • (2003) Drug Metab Dispos , vol.31 , pp. 1199-1202
    • Jalas, J.R.1    Ding, X.2    Murphy, S.E.3
  • 8
    • 13944282327 scopus 로고    scopus 로고
    • Cytochrome P450 enzymes as catalysts of metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-l-butanone (NNK), a tobacco-specific carcinogen
    • Jalas JR, Hecht SS, and Murphy SE (2005) Cytochrome P450 enzymes as catalysts of metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-l-butanone (NNK), a tobacco-specific carcinogen. Chem Res Toxicol 18:95-110.
    • (2005) Chem Res Toxicol , vol.18 , pp. 95-110
    • Jalas, J.R.1    Hecht, S.S.2    Murphy, S.E.3
  • 9
    • 28844479959 scopus 로고    scopus 로고
    • Analysis of coumarin 7-hydroxylation activity of cytochrome P450 2A6 using random mutagenesis
    • Kim D, Wu ZL, and Guengerich FP (2005) Analysis of coumarin 7-hydroxylation activity of cytochrome P450 2A6 using random mutagenesis. J Biol Chem 280:40319-40327.
    • (2005) J Biol Chem , vol.280 , pp. 40319-40327
    • Kim, D.1    Wu, Z.L.2    Guengerich, F.P.3
  • 10
    • 0035498833 scopus 로고    scopus 로고
    • Random mutagenesis of human cytochrome p450 2A6 and screening with indole oxidation products
    • Nakamura K, Martin MV, and Guengerich FP (2001) Random mutagenesis of human cytochrome p450 2A6 and screening with indole oxidation products. Arch Biochem Biophys 395:25-31.
    • (2001) Arch Biochem Biophys , vol.395 , pp. 25-31
    • Nakamura, K.1    Martin, M.V.2    Guengerich, F.P.3
  • 11
    • 78651165715 scopus 로고
    • The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature
    • 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.
    • (1964) J Biol Chem , vol.239 , pp. 2370-2378
    • Omura, T.1    Sato, R.2
  • 12
    • 34547683239 scopus 로고    scopus 로고
    • Structural insight into the altered substrate specificity of human cytochrome P450 2A6 mutants
    • Sansen S, Hsu MH, Stout CD, and Johnson EF (2007) Structural insight into the altered substrate specificity of human cytochrome P450 2A6 mutants. Arch Biochem Biophys 464:197-206.
    • (2007) Arch Biochem Biophys , vol.464 , pp. 197-206
    • Sansen, S.1    Hsu, M.H.2    Stout, C.D.3    Johnson, E.F.4
  • 14
    • 0032967333 scopus 로고    scopus 로고
    • Role of murine cytochrome P-4502F2 in metabolic activation of naphthalene and metabolism of other xenobiotics
    • Shultz MA, Choudary PV, and Buckpitt AR (1999) Role of murine cytochrome P-4502F2 in metabolic activation of naphthalene and metabolism of other xenobiotics. J Pharmacol Exp Ther 290:281-288.
    • (1999) J Pharmacol Exp Ther , vol.290 , pp. 281-288
    • Shultz, M.A.1    Choudary, P.V.2    Buckpitt, A.R.3
  • 16
    • 0344069675 scopus 로고    scopus 로고
    • Expression of cytochrome P450 2A6 in Escherichia coli: Purification, spectral and catalytic characterization, and preparation of polyclonal antibodies
    • Soucek P (1999) Expression of cytochrome P450 2A6 in Escherichia coli: purification, spectral and catalytic characterization, and preparation of polyclonal antibodies. Arch Biochem Biophys 370:190-200.
    • (1999) Arch Biochem Biophys , vol.370 , pp. 190-200
    • Soucek, P.1
  • 17
    • 0034665139 scopus 로고    scopus 로고
    • Human cytochrome P 450 CYP2A13: Predominant expression in the respiratory tract and in high efficiency metabolic activation of a tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone
    • Su T, Bao Z, Zhang QY, Smith TJ, Hong JY, and Ding X (2000) Human cytochrome P 450 CYP2A13: Predominant expression in the respiratory tract and in high efficiency metabolic activation of a tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res 60:5074-5079.
    • (2000) Cancer Res , vol.60 , pp. 5074-5079
    • Su, T.1    Bao, Z.2    Zhang, Q.Y.3    Smith, T.J.4    Hong, J.Y.5    Ding, X.6
  • 18
    • 8444248234 scopus 로고    scopus 로고
    • Roles for epoxidation and detoxification of coumarin in determining species differences in Clara cell toxicity
    • Vas sallo JD, Hicks SM, Born SL, and Das ton GP (2004) Roles for epoxidation and detoxification of coumarin in determining species differences in Clara cell toxicity. Toxicol Sci 82:26-33.
    • (2004) Toxicol Sci , vol.82 , pp. 26-33
    • Vas sallo, J.D.1    Hicks, S.M.2    Born, S.L.3    Das ton, G.P.4
  • 20
    • 0037232920 scopus 로고    scopus 로고
    • CYP 2A13-catalyzed coumarin metabolism, comparison to CYP2A5 and CYP2A6
    • von Weymarn LB and Murphy SE (2003) CYP 2A13-catalyzed coumarin metabolism, comparison to CYP2A5 and CYP2A6. Xenobiotica 33:73-81.
    • (2003) Xenobiotica , vol.33 , pp. 73-81
    • von Weymarn, L.B.1    Murphy, S.E.2
  • 21
    • 4644339625 scopus 로고    scopus 로고
    • Identification of amino acid residues involved in the inactivation of cytochrome P450 2B1 by two acetylenic compounds: The role of three residues in non-substrate recognition sites
    • Von Weymarn LB, Sridar C, and Hollenberg PF (2004) Identification of amino acid residues involved in the inactivation of cytochrome P450 2B1 by two acetylenic compounds: the role of three residues in non-substrate recognition sites. J Pharmacol Exp Ther 311:71-79.
    • (2004) J Pharmacol Exp Ther , vol.311 , pp. 71-79
    • Von Weymarn, L.B.1    Sridar, C.2    Hollenberg, P.F.3
  • 23
    • 12144265866 scopus 로고    scopus 로고
    • Cytochrome P450 2A-catalyzed metabolic activation of structurally similar carcinogenic nitrosamines: W-nitrosonornicotine enantiomers, N-nitrosopiperidine, and N-nitrosopyrrolidine
    • Wong HL, Murphy SE, and Hecht SS (2005a) Cytochrome P450 2A-catalyzed metabolic activation of structurally similar carcinogenic nitrosamines: W-nitrosonornicotine enantiomers, N-nitrosopiperidine, and N-nitrosopyrrolidine. Chem Res Toxicol 18:61-69.
    • (2005) Chem Res Toxicol , vol.18 , pp. 61-69
    • Wong, H.L.1    Murphy, S.E.2    Hecht, S.S.3
  • 24
    • 21144437181 scopus 로고    scopus 로고
    • Metabolic activation of the tobacco carcinogen 4-(methylnitrosamino)-(3- pyridyl)-1-butanone by cytochrome P450 2A13 in human fetal nasal microsomes
    • Wong HL, Zhang X, Zhang QY, Gu J, Ding X, Hecht SS, and Murphy SE (2005b) Metabolic activation of the tobacco carcinogen 4-(methylnitrosamino)-(3- pyridyl)-1-butanone by cytochrome P450 2A13 in human fetal nasal microsomes. Chem Res Toxicol 18:913-918.
    • (2005) Chem Res Toxicol , vol.18 , pp. 913-918
    • Wong, H.L.1    Zhang, X.2    Zhang, Q.Y.3    Gu, J.4    Ding, X.5    Hecht, S.S.6    Murphy, S.E.7
  • 25
    • 26944462419 scopus 로고    scopus 로고
    • Structures of human microsomal cytochrome P450 2A6 complexed with coumarin and methoxsalen
    • Yano JK, Hsu MH, Griffin KJ, Stout CD, and Johnson EF (2005) Structures of human microsomal cytochrome P450 2A6 complexed with coumarin and methoxsalen. Nat Struct Mol Biol 12:822-823.
    • (2005) Nat Struct Mol Biol , vol.12 , pp. 822-823
    • Yano, J.K.1    Hsu, M.H.2    Griffin, K.J.3    Stout, C.D.4    Johnson, E.F.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.