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Volumn 36, Issue 12, 2008, Pages 2582-2590

Key residues controlling phenacetin metabolism by human cytochrome P450 2A enzymes

Author keywords

[No Author keywords available]

Indexed keywords

AFLATOXIN B1; COTININE; CYTOCHROME P450 2A; CYTOCHROME P450 2A13; CYTOCHROME P450 2A6; NICOTINE; PHENACETIN; UNCLASSIFIED DRUG;

EID: 57349177563     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.108.023770     Document Type: Article
Times cited : (38)

References (29)
  • 1
    • 13444274285 scopus 로고    scopus 로고
    • Metabolism of nicotine and cotinine by human cytochrome P450 2A13
    • Bao Z, He XY, Ding X, Prabhu S, and Hong JY (2005) Metabolism of nicotine and cotinine by human cytochrome P450 2A13. Drug Metab Dispos 33:258-261.
    • (2005) Drug Metab Dispos , vol.33 , pp. 258-261
    • Bao, Z.1    He, X.Y.2    Ding, X.3    Prabhu, S.4    Hong, J.Y.5
  • 2
    • 0028103275 scopus 로고
    • Number 4 (1994) The CCP4 suite: Programs for protein crystallography
    • Collaborative Computer Project
    • Collaborative Computer Project, Number 4 (1994) The CCP4 suite: programs for protein crystallography. (1994) Acta Crystallogr D Biol Crystallogr 50:760-763.
    • (1994) Acta Crystallogr D Biol Crystallogr , vol.50 , pp. 760-763
  • 4
    • 13244281317 scopus 로고    scopus 로고
    • Coot: Model-building tools for molecular graphics
    • Emsley P and Cowtan K (2004) Coot: model-building tools for molecular graphics. Acta Crystallogr D Biol Crystallogr 60:2126-2132.
    • (2004) Acta Crystallogr D Biol Crystallogr , vol.60 , pp. 2126-2132
    • Emsley, P.1    Cowtan, K.2
  • 5
  • 6
    • 0021990937 scopus 로고
    • Additional routes in the metabolism of phenacetin
    • Fischbach T and Lenk W (1985a) Additional routes in the metabolism of phenacetin. Xenobiotica 15:149-164.
    • (1985) Xenobiotica , vol.15 , pp. 149-164
    • Fischbach, T.1    Lenk, W.2
  • 7
    • 0022372060 scopus 로고
    • The metabolism of N-hydroxyphenacetin in vitro and in vivo
    • Fischbach T and Lenk W (1985b) The metabolism of N-hydroxyphenacetin in vitro and in vivo. Xenobiotica 15:915-927.
    • (1985) Xenobiotica , vol.15 , pp. 915-927
    • Fischbach, T.1    Lenk, W.2
  • 8
    • 0002634779 scopus 로고
    • Analgesic-antipyretics and anti-inflammatory agents
    • Gilman AG, Gilman LS, Rall TW, and Murad G eds pp, Macmillan, New York
    • Flower RJ, Moncada S, and Vane JR (1985) Analgesic-antipyretics and anti-inflammatory agents, in Goodman and Gilman's The Pharmacological Basis of Therapeutics (Gilman AG, Gilman LS, Rall TW, and Murad G eds) pp 674-715, Macmillan, New York.
    • (1985) Goodman and Gilman's The Pharmacological Basis of Therapeutics , pp. 674-715
    • Flower, R.J.1    Moncada, S.2    Vane, J.R.3
  • 9
    • 41849093006 scopus 로고    scopus 로고
    • Human cytochrome P450 2A13 efficiently metabolizes chemicals in air pollutants: Naphthalene, styrene, and toluene
    • Fukami T, Katoh M, Yamazaki H, Yokoi T, and Nakajima M (2008) Human cytochrome P450 2A13 efficiently metabolizes chemicals in air pollutants: naphthalene, styrene, and toluene. Chem Res Toxicol 21:720-725.
    • (2008) Chem Res Toxicol , vol.21 , pp. 720-725
    • Fukami, T.1    Katoh, M.2    Yamazaki, H.3    Yokoi, T.4    Nakajima, M.5
  • 10
    • 33847387556 scopus 로고    scopus 로고
    • CYP2A13 metabolizes the substrates of human CYP1A2, phenacetin, and theophylline
    • Fukami T, Nakajima M, Sakai H, Katoh M, and Yokoi T (2007) CYP2A13 metabolizes the substrates of human CYP1A2, phenacetin, and theophylline. Drug Metab Dispos 35:335-339.
    • (2007) Drug Metab Dispos , vol.35 , pp. 335-339
    • Fukami, T.1    Nakajima, M.2    Sakai, H.3    Katoh, M.4    Yokoi, T.5
  • 11
    • 9444285919 scopus 로고    scopus 로고
    • Identification of critical amino acid residues of human metabolic activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-tobaccospecific carcinogen
    • He XY, Shen J, Ding X, Lu AY, and Hong JY (2004a) Identification of critical amino acid residues of human metabolic activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-tobaccospecific carcinogen. Drug Metab Dispos 32:1516-1521.
    • (2004) Drug Metab Dispos , vol.32 , pp. 1516-1521
    • He, X.Y.1    Shen, J.2    Ding, X.3    Lu, A.Y.4    Hong, J.Y.5
  • 12
    • 2942605963 scopus 로고    scopus 로고
    • 372 as critical amino acid residues for the activity difference between human CYP2A6 and CYP2A13 in coumarin 7-hydroxylation
    • 372 as critical amino acid residues for the activity difference between human CYP2A6 and CYP2A13 in coumarin 7-hydroxylation. Arch Biochem Biophys 427:143-153.
    • (2004) Arch Biochem Biophys , vol.427 , pp. 143-153
    • He, X.Y.1    Shen, J.2    Hu, W.Y.3    Ding, X.4    Lu, A.Y.5    Hong, J.Y.6
  • 13
    • 33646346615 scopus 로고    scopus 로고
    • Efficient activation of aflatoxin B1 by cytochrome P450 2A13, an enzyme predominantly expressed in human respiratory tract
    • He XY, Tang L, Wang SL, Cai QS, Wang JS, and Hong JY (2006) Efficient activation of aflatoxin B1 by cytochrome P450 2A13, an enzyme predominantly expressed in human respiratory tract. Int J Cancer 118:2665-2671.
    • (2006) Int J Cancer , vol.118 , pp. 2665-2671
    • He, X.Y.1    Tang, L.2    Wang, S.L.3    Cai, Q.S.4    Wang, J.S.5    Hong, J.Y.6
  • 14
    • 0027995683 scopus 로고
    • Detection, delineation, measurement and display of cavities in macromolecular structures
    • Kleywegt GJ and Jones TA (1994) Detection, delineation, measurement and display of cavities in macromolecular structures. Acta Crystallogr D Biol Crystallogr 50:178-185.
    • (1994) Acta Crystallogr D Biol Crystallogr , vol.50 , pp. 178-185
    • Kleywegt, G.J.1    Jones, T.A.2
  • 15
    • 0000243829 scopus 로고
    • PROCHECK: A program to check the stereochemical quality of protein structures
    • Laskowski RA, MacArthur MW, Moss DS, and Thornton JM (1993) PROCHECK: a program to check the stereochemical quality of protein structures. J Appl Crystallogr 26:283-291.
    • (1993) J Appl Crystallogr , vol.26 , pp. 283-291
    • Laskowski, R.A.1    MacArthur, M.W.2    Moss, D.S.3    Thornton, J.M.4
  • 16
    • 33644874235 scopus 로고    scopus 로고
    • The integration of macromolecular diffraction data
    • Leslie AG (2006) The integration of macromolecular diffraction data. Acta Crystallogr D Biol Crystallogr 62:48-57.
    • (2006) Acta Crystallogr D Biol Crystallogr , vol.62 , pp. 48-57
    • Leslie, A.G.1
  • 20
    • 0030471840 scopus 로고    scopus 로고
    • The roles of individual amino acids in altering substrate specificity of the P450 2a4/2a5 enzymes
    • Negishi M, Uno T, Honkakoski P, Sueyoshi T, Darden TA, and Pedersen LP (1996) The roles of individual amino acids in altering substrate specificity of the P450 2a4/2a5 enzymes. Biochimie 78:685-694.
    • (1996) Biochimie , vol.78 , pp. 685-694
    • Negishi, M.1    Uno, T.2    Honkakoski, P.3    Sueyoshi, T.4    Darden, T.A.5    Pedersen, L.P.6
  • 21
    • 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 (2007a) 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
  • 22
    • 34347235844 scopus 로고    scopus 로고
    • Adaptations for the oxidation of polycyclic aromatic hydrocarbons exhibited by the structure of human P450 1A2
    • Sansen S, Yano JK, Reynald RL, Schoch GA, Griffin KJ, Stout CD, and Johnson EF (2007b) Adaptations for the oxidation of polycyclic aromatic hydrocarbons exhibited by the structure of human P450 1A2. J Biol Chem 282:14348-14355.
    • (2007) J Biol Chem , vol.282 , pp. 14348-14355
    • Sansen, S.1    Yano, J.K.2    Reynald, R.L.3    Schoch, G.A.4    Griffin, K.J.5    Stout, C.D.6    Johnson, E.F.7
  • 25
    • 0034665139 scopus 로고    scopus 로고
    • Human cytochrome P450 CYP2A13: Predominant expression in the respiratory tract and its 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 P450 CYP2A13: predominant expression in the respiratory tract and its 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
  • 26
    • 0025398721 scopus 로고
    • WHAT IF: A molecular modeling and drug design program
    • Vriend G (1990) WHAT IF: a molecular modeling and drug design program. J Mol Graph 8:52-56, 29.
    • (1990) J Mol Graph , vol.8
    • Vriend, G.1
  • 27
    • 28844494791 scopus 로고    scopus 로고
    • Expansion of substrate specificity of cytochrome P450 2A6 by random and site-directed mutagenesis
    • Wu ZL, Podust LM, and Guengerich FP (2005) Expansion of substrate specificity of cytochrome P450 2A6 by random and site-directed mutagenesis. J Biol Chem 280:41090-41100.
    • (2005) J Biol Chem , vol.280 , pp. 41090-41100
    • Wu, Z.L.1    Podust, L.M.2    Guengerich, F.P.3
  • 28
    • 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
  • 29
    • 33845348869 scopus 로고    scopus 로고
    • Xenobiotic-metabolizing enzymes in human lung
    • Zhang JY, Wang Y, and Prakash C (2006) Xenobiotic-metabolizing enzymes in human lung. Curr Drug Metab 7:939-948.
    • (2006) Curr Drug Metab , vol.7 , pp. 939-948
    • Zhang, J.Y.1    Wang, Y.2    Prakash, C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.