메뉴 건너뛰기




Volumn 82, Issue 5, 2012, Pages 835-842

Cytochrome P450 architecture and cysteine nucleophile placement impact raloxifene-mediated mechanism-based inactivation

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE; CYTOCHROME P450 1A2; CYTOCHROME P450 2C19; CYTOCHROME P450 2C8; CYTOCHROME P450 2C9; CYTOCHROME P450 2D6; CYTOCHROME P450 2E1; CYTOCHROME P450 3A5; GLUTATHIONE; RALOXIFENE;

EID: 84867779013     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.112.080739     Document Type: Article
Times cited : (20)

References (47)
  • 1
    • 34447133553 scopus 로고    scopus 로고
    • Time-dependent inactivation of P450 3A4 by raloxifene: Identification of Cys239 as the site of apoprotein alkylation
    • DOI 10.1021/tx700037e
    • Baer BR, Wienkers LC, and Rock DA (2007) Time-dependent inactivation of P450 3A4 by raloxifene: identification of Cys239 as the site of apoprotein alkylation. Chem Res Toxicol 20:954-964. (Pubitemid 47035350)
    • (2007) Chemical Research in Toxicology , vol.20 , Issue.6 , pp. 954-964
    • Baer, B.R.1    Wienkers, L.C.2    Rock, D.A.3
  • 2
    • 0024849826 scopus 로고
    • The use of mass spectrometry in the study of chemically-reactive drug metabolites. Application of MS/MS and LC/MS to the analysis of glutathione- and related S-linked conjugates of N-methylformamide
    • DOI 10.1016/0731-7085(89)80140-2
    • Baillie TA, Pearson PG, Rashed MS, and Howald WN (1989) The use of mass spectrometry in the study of chemically-reactive drug metabolites. Application of MS/MS and LC/MS to the analysis of glutathione- and related S-linked conjugates of N-methylformamide. J Pharm Biomed Anal 7:1351-1360. (Pubitemid 20253557)
    • (1989) Journal of Pharmaceutical and Biomedical Analysis , vol.7 , Issue.12 , pp. 1351-1360
    • Baillie, T.A.1    Pearson, P.G.2    Rashed, M.S.3    Howald, W.N.4
  • 4
    • 0027475989 scopus 로고
    • Determinants of protein modification versus heme alkylation: Inactivation of cytochrome P450 1A1 by 1-ethynylpyrene and phenylacetylene
    • DOI 10.1021/tx00031a006
    • Chan WK, Sui Z, and Ortiz de Montellano PR (1993) Determinants of protein modification versus heme alkylation: inactivation of cytochrome P450 1A1 by 1-ethynylpyrene and phenylacetylene. Chem Res Toxicol 6:38-45. (Pubitemid 23040370)
    • (1993) Chemical Research in Toxicology , vol.6 , Issue.1 , pp. 38-45
    • Chan, W.K.1    Sui, Z.2    De Montellano, P.R.O.3
  • 6
    • 0034792157 scopus 로고    scopus 로고
    • Structural, redox, and mechanistic parameters for cysteine-sulfenic acid function in catalysis and regulation
    • DOI 10.1016/S0065-3233(01)58006-7
    • Claiborne A, Mallett TC, Yeh JI, Luba J, and Parsonage D (2001) Structural, redox, and mechanistic parameters for cysteine-sulfenic acid function in catalysis and regulation. Adv Protein Chem 58:215-276. (Pubitemid 32954368)
    • (2001) Advances in Protein Chemistry , vol.58 , pp. 215-276
    • Claiborne, A.1    Mallett, T.C.2    Yeh, J.I.3    Luba, J.4    Parsonage, D.5
  • 7
    • 0021345926 scopus 로고
    • N-acetyl-p-benzoquinone imine: A cytochrome P-450-mediated oxidation product of acetaminophen
    • Dahlin DC, Miwa GT, Lu AY, and Nelson SD (1984) N-acetyl-p-benzoquinone imine: a cytochrome P-450-mediated oxidation product of acetaminophen. Proc Natl Acad Sci USA 81:1327-1331. (Pubitemid 14173462)
    • (1984) ISOTOPENPRAXIS , vol.20 , Issue.1 , pp. 1327-1331
    • Dahlin, D.C.1    Miwa, G.T.2    Lu, A.Y.H.3    Nelson, S.D.4
  • 8
    • 84862649353 scopus 로고    scopus 로고
    • In vitro hepatotoxicity and cytochrome P450 induction and inhibition characteristics of carnosic acid, a dietary supplement with antiadipogenic properties
    • Dickmann LJ, VandenBrink BM, and Lin YS (2012) In vitro hepatotoxicity and cytochrome P450 induction and inhibition characteristics of carnosic acid, a dietary supplement with antiadipogenic properties. Drug Metab Dispos 40:1263-1267.
    • (2012) Drug Metab Dispos , vol.40 , pp. 1263-1267
    • Dickmann, L.J.1    VandenBrink, B.M.2    Lin, Y.S.3
  • 10
    • 84855890551 scopus 로고    scopus 로고
    • Substrate selectivity of drug-metabolizing cytochrome P450s predicted from crystal structures and in silico modeling
    • Dong D and Wu B (2012) Substrate selectivity of drug-metabolizing cytochrome P450s predicted from crystal structures and in silico modeling. Drug Metab Rev 44:1-17.
    • (2012) Drug Metab Rev , vol.44 , pp. 1-17
    • Dong, D.1    Wu, B.2
  • 12
    • 0034973773 scopus 로고    scopus 로고
    • Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity
    • Guengerich FP (2001) Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem Res Toxicol 14:611-650.
    • (2001) Chem Res Toxicol , vol.14 , pp. 611-650
    • Guengerich, F.P.1
  • 13
    • 79959385330 scopus 로고    scopus 로고
    • Structure and function of cytochromes P450 2B: From mechanism-based inactivators to X-ray crystal structures and back
    • Halpert JR (2011) Structure and function of cytochromes P450 2B: from mechanism-based inactivators to X-ray crystal structures and back. Drug Metab Dispos 39:1113-1121.
    • (2011) Drug Metab Dispos , vol.39 , pp. 1113-1121
    • Halpert, J.R.1
  • 14
    • 77952312729 scopus 로고    scopus 로고
    • Sequential metabolism of secondary alkyl amines to metabolic-intermediate complexes: Opposing roles for the secondary hydroxylamine and primary amine metabolites of desipramine, (s)-fluoxetine, and N-desmethyldiltiazem
    • Hanson KL, VandenBrink BM, Babu KN, Allen KE, Nelson WL, and Kunze KL (2010) Sequential metabolism of secondary alkyl amines to metabolic-intermediate complexes: opposing roles for the secondary hydroxylamine and primary amine metabolites of desipramine, (s)-fluoxetine, and N-desmethyldiltiazem. Drug Metab Dispos 38:963-972.
    • (2010) Drug Metab Dispos , vol.38 , pp. 963-972
    • Hanson, K.L.1    VandenBrink, B.M.2    Babu, K.N.3    Allen, K.E.4    Nelson, W.L.5    Kunze, K.L.6
  • 15
    • 84862674138 scopus 로고    scopus 로고
    • Sequential metabolism of AMG 487, a novel CXCR3 antagonist, results in formation of quinone reactive metabolites that covalently modify CYP3A4 Cys239 and cause time-dependent inhibition of the enzyme
    • Henne KR, Tran TB, VandenBrink BM, Rock DA, Aidasani DK, Subramanian R, Mason AK, Stresser DM, Teffera Y, Wong SG, et al. (2012) Sequential metabolism of AMG 487, a novel CXCR3 antagonist, results in formation of quinone reactive metabolites that covalently modify CYP3A4 Cys239 and cause time-dependent inhibition of the enzyme. Drug Metab Dispos 40:1429-1440.
    • (2012) Drug Metab Dispos , vol.40 , pp. 1429-1440
    • Henne, K.R.1    Tran, T.B.2    VandenBrink, B.M.3    Rock, D.A.4    Aidasani, D.K.5    Subramanian, R.6    Mason, A.K.7    Stresser, D.M.8    Teffera, Y.9    Wong, S.G.10
  • 16
    • 1342331932 scopus 로고    scopus 로고
    • Mechanism-Based Inactivation of Cytochrome P450 2D6 by 1-[(2-Ethyl-4-methyl-1H-imidazol-5-yl)methyl]-4-[4-(trifluoromethyl) -2-pyridinyl]piperazine: Kinetic Characterization and Evidence for Apoprotein Adduction
    • DOI 10.1021/tx034199f
    • Hutzler JM, Steenwyk RC, Smith EB, Walker GS, and Wienkers LC (2004) Mechanism-based inactivation of cytochrome P450 2D6 by 1-[(2-ethyl-4-methyl-1H- imidazol-5-yl)methyl]-4-[4-(trifluoromethyl)-2-pyridinyl]piperazine: kinetic characterization and evidence for apoprotein adduction. Chem Res Toxicol 17:174-184. (Pubitemid 38252497)
    • (2004) Chemical Research in Toxicology , vol.17 , Issue.2 , pp. 174-184
    • Hutzler, J.M.1    Steenwyk, R.C.2    Smith, E.B.3    Walker, G.S.4    Wienkers, L.C.5
  • 17
    • 27544516024 scopus 로고    scopus 로고
    • Structural diversity of human xenobiotic-metabolizing cytochrome P450 monooxygenases
    • DOI 10.1016/j.bbrc.2005.08.190, PII S0006291X05019169
    • Johnson EF and Stout CD (2005) Structural diversity of human xenobioticmetabolizing cytochrome P450 monooxygenases. Biochem Biophys Res Commun 338:331-336. (Pubitemid 41540575)
    • (2005) Biochemical and Biophysical Research Communications , vol.338 , Issue.1 , pp. 331-336
    • Johnson, E.F.1    Stout, C.D.2
  • 18
    • 70350273017 scopus 로고    scopus 로고
    • Structural alerts, reactive metabolites, and protein covalent binding: How reliable are these attributes as predictors of drug toxicity?
    • Kalgutkar AS and Didiuk MT (2009) Structural alerts, reactive metabolites, and protein covalent binding: how reliable are these attributes as predictors of drug toxicity? Chem Biodivers 6:2115-2137.
    • (2009) Chem Biodivers , vol.6 , pp. 2115-2137
    • Kalgutkar, A.S.1    Didiuk, M.T.2
  • 19
    • 34548805504 scopus 로고    scopus 로고
    • Mechanism-based inactivation of cytochrome P450 enzymes: Chemical mechanisms, structure-activity relationships and relationship to clinical drug-drug interactions and idiosyncratic adverse drug reactions
    • DOI 10.2174/138920007780866807
    • Kalgutkar AS, Obach RS, and Maurer TS (2007) Mechanism-based inactivation of cytochrome P450 enzymes: chemical mechanisms, structure-activity relationships and relationship to clinical drug-drug interactions and idiosyncratic adverse drug reactions. Curr Drug Metab 8:407-447. (Pubitemid 47603408)
    • (2007) Current Drug Metabolism , vol.8 , Issue.5 , pp. 407-447
    • Kalgutkar, A.S.1    Obach, R.S.2    Maurer, T.S.3
  • 20
    • 40949102296 scopus 로고    scopus 로고
    • CYP3A4-mediated carbamazepine (CBZ) metabolism: Formation of a covalent CBZ-CYP3A4 adduct and alteration of the enzyme kinetic profile
    • DOI 10.1124/dmd.107.016501
    • Kang P, Liao M, Wester MR, Leeder JS, Pearce RE, and Correia MA (2008) CYP3A4-Mediated carbamazepine (CBZ) metabolism: formation of a covalent CBZ-CYP3A4 adduct and alteration of the enzyme kinetic profile. Drug Metab Dispos 36:490-499. (Pubitemid 351409335)
    • (2008) Drug Metabolism and Disposition , vol.36 , Issue.3 , pp. 490-499
    • Kang, P.1    Liao, M.2    Wester, M.R.3    Leeder, J.S.4    Pearce, R.E.5    Correia, M.A.6
  • 21
    • 0036266936 scopus 로고    scopus 로고
    • Characterization of raloxifene glucuronidation in vitro: Contribution of intestinal metabolism to presystemic clearance
    • DOI 10.1124/dmd.30.6.694
    • Kemp DC, Fan PW, and Stevens JC (2002) Characterization of raloxifene glucuronidation in vitro: contribution of intestinal metabolism to presystemic clearance. Drug Metab Dispos 30:694-700. (Pubitemid 34579104)
    • (2002) Drug Metabolism and Disposition , vol.30 , Issue.6 , pp. 694-700
    • Kemp, D.C.1    Fan, P.W.2    Stevens, J.C.3
  • 22
    • 0027380074 scopus 로고
    • Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline
    • Kunze KL and Trager WF (1993) Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline. Chem Res Toxicol 6:649-656. (Pubitemid 23290017)
    • (1993) Chemical Research in Toxicology , vol.6 , Issue.5 , pp. 649-656
    • Kunze, K.L.1    Trager, W.F.2
  • 23
    • 84855873678 scopus 로고    scopus 로고
    • Metabolic activation in drug-induced liver injury
    • Leung L, Kalgutkar AS, and Obach RS (2012) Metabolic activation in drug-induced liver injury. Drug Metab Rev 44:18-33.
    • (2012) Drug Metab Rev , vol.44 , pp. 18-33
    • Leung, L.1    Kalgutkar, A.S.2    Obach, R.S.3
  • 24
    • 0030036211 scopus 로고    scopus 로고
    • Molecular modelling of CYP1A subfamily members based on an alignment with CYP102: Rationalization of CYP1A substrate specificity in terms of active site amino acid residues
    • Lewis DF and Lake BG (1996) Molecular modelling of CYP1A subfamily members based on an alignment with CYP102: rationalization of CYP1A substrate specificity in terms of active site amino acid residues. Xenobiotica 26:723-753. (Pubitemid 26233025)
    • (1996) Xenobiotica , vol.26 , Issue.7 , pp. 723-753
    • Lewis, D.F.V.1    Lake, B.G.2
  • 26
    • 84859915424 scopus 로고    scopus 로고
    • Identification of the residue in human CYP3A4 that is covalently modified by bergamottin and the reactive intermediate that contributes to the grapefruit juice effect
    • Lin HL, Kenaan C, and Hollenberg PF (2012) Identification of the residue in human CYP3A4 that is covalently modified by bergamottin and the reactive intermediate that contributes to the grapefruit juice effect. Drug Metab Dispos 40:998-1006.
    • (2012) Drug Metab Dispos , vol.40 , pp. 998-1006
    • Lin, H.L.1    Kenaan, C.2    Hollenberg, P.F.3
  • 27
    • 0029866602 scopus 로고    scopus 로고
    • Activation of heat shock factor by alkylating agents is triggered by glutathione depletion and oxidation of protein thiols
    • DOI 10.1074/jbc.271.9.4805
    • Liu H, Lightfoot R, and Stevens JL (1996) Activation of heat shock factor by alkylating agents is triggered by glutathione depletion and oxidation of protein thiols. J Biol Chem 271:4805-4812. (Pubitemid 26074965)
    • (1996) Journal of Biological Chemistry , vol.271 , Issue.9 , pp. 4805-4812
    • Liu, H.1    Lightfoot, R.2    Stevens, J.L.3
  • 28
    • 0142243111 scopus 로고    scopus 로고
    • Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, A 5-lipoxygenase inhibitor
    • DOI 10.1124/dmd.31.11.1352
    • Lu P, Schrag ML, Slaughter DE, Raab CE, Shou M, and Rodrigues AD (2003) Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor. Drug Metab Dispos 31:1352-1360. (Pubitemid 37310324)
    • (2003) Drug Metabolism and Disposition , vol.31 , Issue.11 , pp. 1352-1360
    • Lu, P.1    Schrag, M.L.2    Slaughter, D.E.3    Raab, C.E.4    Shou, M.5    Rodrigues, A.D.6
  • 30
    • 77952806659 scopus 로고    scopus 로고
    • CYP3A4-Mediated oxygenation versus dehydrogenation of raloxifene
    • Moore CD, Reilly CA, and Yost GS (2010) CYP3A4-Mediated oxygenation versus dehydrogenation of raloxifene. Biochemistry 49:4466-4475.
    • (2010) Biochemistry , vol.49 , pp. 4466-4475
    • Moore, C.D.1    Reilly, C.A.2    Yost, G.S.3
  • 31
    • 0020325715 scopus 로고
    • Metabolic activation and drug toxicity
    • Nelson SD (1982) Metabolic activation and drug toxicity. J Med Chem 25:753-765.
    • (1982) J Med Chem , vol.25 , pp. 753-765
    • Nelson, S.D.1
  • 32
    • 38149048655 scopus 로고    scopus 로고
    • Differential time-dependent inactivation of P450 3A4 and P450 3A5 by raloxifene: A key role for C239 in quenching reactive intermediates
    • Pearson JT, Wahlstrom JL, Dickmann LJ, Kumar S, Halpert JR, Wienkers LC, Foti RS, and Rock DA (2007) Differential time-dependent inactivation of P450 3A4 and P450 3A5 by raloxifene: a key role for C239 in quenching reactive intermediates. Chem Res Toxicol 20:1778-1786.
    • (2007) Chem Res Toxicol , vol.20 , pp. 1778-1786
    • Pearson, J.T.1    Wahlstrom, J.L.2    Dickmann, L.J.3    Kumar, S.4    Halpert, J.R.5    Wienkers, L.C.6    Foti, R.S.7    Rock, D.A.8
  • 35
    • 0026509008 scopus 로고
    • The reactivity of thiols and disulfides with different redox states of myoglobin. Redox and addition reactions and formation of thiyl radical intermediates
    • Romero FJ, Ordoñez I, Arduini A, and Cadenas E (1992) The reactivity of thiols and disulfides with different redox states of myoglobin. Redox and addition reactions and formation of thiyl radical intermediates. J Biol Chem 267:1680-1688.
    • (1992) J Biol Chem , vol.267 , pp. 1680-1688
    • Romero, F.J.1    Ordoñez, I.2    Arduini, A.3    Cadenas, E.4
  • 36
  • 37
    • 47749092044 scopus 로고    scopus 로고
    • Determinants of cytochrome P450 2C8 substrate binding: Structures of complexes with montelukast, troglitazone, felodipine, and 9-cis-retinoic acid
    • Schoch GA, Yano JK, Sansen S, Dansette PM, Stout CD, and Johnson EF (2008) Determinants of cytochrome P450 2C8 substrate binding: structures of complexes with montelukast, troglitazone, felodipine, and 9-cis-retinoic acid. J Biol Chem 283:17227-17237.
    • (2008) J Biol Chem , vol.283 , pp. 17227-17237
    • Schoch, G.A.1    Yano, J.K.2    Sansen, S.3    Dansette, P.M.4    Stout, C.D.5    Johnson, E.F.6
  • 38
    • 81555222817 scopus 로고    scopus 로고
    • Structures of cytochrome P450 2B6 bound to 4-benzylpyridine and 4-(4-nitrobenzyl)pyridine: Insight into inhibitor binding and rearrangement of active site side chains
    • Shah MB, Pascual J, Zhang Q, Stout CD, and Halpert JR (2011) Structures of cytochrome P450 2B6 bound to 4-benzylpyridine and 4-(4-nitrobenzyl)pyridine: insight into inhibitor binding and rearrangement of active site side chains. Mol Pharmacol 80:1047-1055.
    • (2011) Mol Pharmacol , vol.80 , pp. 1047-1055
    • Shah, M.B.1    Pascual, J.2    Zhang, Q.3    Stout, C.D.4    Halpert, J.R.5
  • 40
    • 80053004364 scopus 로고    scopus 로고
    • Structural alert/reactive metabolite concept as applied in medicinal chemistry to mitigate the risk of idiosyncratic drug toxicity: A perspective based on the critical examination of trends in the top 200 drugs marketed in the United States
    • Stepan AF, Walker DP, Bauman J, Price DA, Baillie TA, Kalgutkar AS, and Aleo MD (2011) Structural alert/reactive metabolite concept as applied in medicinal chemistry to mitigate the risk of idiosyncratic drug toxicity: a perspective based on the critical examination of trends in the top 200 drugs marketed in the United States. Chem Res Toxicol 24:1345-1410.
    • (2011) Chem Res Toxicol , vol.24 , pp. 1345-1410
    • Stepan, A.F.1    Walker, D.P.2    Bauman, J.3    Price, D.A.4    Baillie, T.A.5    Kalgutkar, A.S.6    Aleo, M.D.7
  • 41
    • 73849120796 scopus 로고    scopus 로고
    • The role of metabolites in predicting drug-drug interactions: Focus on irreversible cytochrome P450 inhibition
    • VandenBrink BM and Isoherranen N (2010) The role of metabolites in predicting drug-drug interactions: focus on irreversible cytochrome P450 inhibition. Curr Opin Drug Discov Devel 13:66-77.
    • (2010) Curr Opin Drug Discov Devel , vol.13 , pp. 66-77
    • VandenBrink, B.M.1    Isoherranen, N.2
  • 42
    • 13544275575 scopus 로고    scopus 로고
    • Fluorescent photoaffinity labeling of cytochrome p450 3a4 by lapachenole: Identification of modification sites by mass spectrometry
    • DOI 10.1021/bi048228c
    • Wen B, Doneanu CE, Gartner CA, Roberts AG, Atkins WM, and Nelson SD (2005) Fluorescent photoaffinity labeling of cytochrome P450 3A4 by lapachenole: identification of modification sites by mass spectrometry. Biochemistry 44:1833-1845. (Pubitemid 40223615)
    • (2005) Biochemistry , vol.44 , Issue.6 , pp. 1833-1845
    • Wen, B.1    Doneanuj, C.E.2    Gartner, C.A.3    Roberts, A.G.4    Atkins, W.M.5    Nelson, S.D.6
  • 44
    • 27644596457 scopus 로고    scopus 로고
    • Predicting in vivo drug interactions from in vitro drug discovery data
    • DOI 10.1038/nrd1851, PII N1851
    • Wienkers LC and Heath TG (2005) Predicting in vivo drug interactions from in vitro drug discovery data. Nat Rev Drug Discov 4:825-833. (Pubitemid 41553963)
    • (2005) Nature Reviews Drug Discovery , vol.4 , Issue.10 , pp. 825-833
    • Wienkers, L.C.1    Heath, T.G.2
  • 45
    • 4644301430 scopus 로고    scopus 로고
    • The structure of human microsomal cytochrome P450 3A4 determined by X-ray crystallography to 2.05-A resolution
    • DOI 10.1074/jbc.C400293200
    • Yano JK, Wester MR, Schoch GA, Griffin KJ, Stout CD, and Johnson EF (2004) The structure of human microsomal cytochrome P450 3A4 determined by X-ray crystallography to 2.05-A resolution. J Biol Chem 279:38091-38094. (Pubitemid 39295952)
    • (2004) Journal of Biological Chemistry , vol.279 , Issue.37 , pp. 38091-38094
    • Yano, J.K.1    Wester, M.R.2    Schoch, G.A.3    Griffin, K.J.4    Stout, C.D.5    Johnson, E.F.6
  • 47
    • 35848962726 scopus 로고    scopus 로고
    • Identification of cytochrome P450 3A4 modification site with reactive metabolite using linear ion trap-fourier transform mass spectrometry
    • DOI 10.1021/tx700165q
    • Yukinaga H, Takami T, Shioyama SH, Tozuka Z, Masumoto H, Okazaki O, and Sudo K (2007) Identification of cytochrome P450 3A4 modification site with reactive metabolite using linear ion trap-Fourier transform mass spectrometry. Chem Res Toxicol 20:1373-1378. (Pubitemid 350057206)
    • (2007) Chemical Research in Toxicology , vol.20 , Issue.10 , pp. 1373-1378
    • Yukinaga, H.1    Takami, T.2    Shioyama, S.-H.3    Tozuka, Z.4    Masumoto, H.5    Okazaki, O.6    Sudo, K.-I.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.