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Volumn 50, Issue 6, 2007, Pages 1158-1165

Use of simple docking methods to screen a virtual library for heteroactivators of cytochrome P450 2C9

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450 2C9; CYTOCHROME P450 INHIBITOR; DAPSONE; DAPSONE DERIVATIVE; ENZYME ACTIVATOR;

EID: 33947705581     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060706p     Document Type: Article
Times cited : (30)

References (40)
  • 1
    • 2642570170 scopus 로고    scopus 로고
    • Moving towards individualized medicine with pharmacogenomics
    • Evans, W. E.; Relling, M. V. Moving towards individualized medicine with pharmacogenomics. Nature 2004, 429, 464-468.
    • (2004) Nature , vol.429 , pp. 464-468
    • Evans, W.E.1    Relling, M.V.2
  • 2
    • 33644861762 scopus 로고    scopus 로고
    • Inhibition constants, inhibitor concentrations and the prediction of inhibitory drug drug interactions: Pitfalls, progress and promise
    • Bachmann, K. A. Inhibition constants, inhibitor concentrations and the prediction of inhibitory drug drug interactions: pitfalls, progress and promise. Curr. Drug Metab. 2006, 7, 1-14.
    • (2006) Curr. Drug Metab , vol.7 , pp. 1-14
    • Bachmann, K.A.1
  • 3
    • 27644596457 scopus 로고    scopus 로고
    • Predicting in vivo drug interactions from in vitro drug discovery data
    • Wienkers, L. C.; Heath, T. G. Predicting in vivo drug interactions from in vitro drug discovery data. Nat. Rev. Drug Discovery 2005, 4, 825-833.
    • (2005) Nat. Rev. Drug Discovery , vol.4 , pp. 825-833
    • Wienkers, L.C.1    Heath, T.G.2
  • 4
    • 13844308070 scopus 로고    scopus 로고
    • Non-Michaelis-Menten kinetics in cytochrome P450-catalyzed reactions
    • Atkins, W. M. Non-Michaelis-Menten kinetics in cytochrome P450-catalyzed reactions. Annu. Rev. Pharmacol. Toxicol. 2005, 45, 291-310.
    • (2005) Annu. Rev. Pharmacol. Toxicol , vol.45 , pp. 291-310
    • Atkins, W.M.1
  • 5
    • 3042608648 scopus 로고    scopus 로고
    • Modeling kinetic data from in vitro drug metabolism enzyme experiments
    • Tracy, T. S.; Hummel, M. A. Modeling kinetic data from in vitro drug metabolism enzyme experiments. Drug Metab. Rev. 2004, 36, 231-242.
    • (2004) Drug Metab. Rev , vol.36 , pp. 231-242
    • Tracy, T.S.1    Hummel, M.A.2
  • 6
    • 0037048522 scopus 로고    scopus 로고
    • Pyrene.pyrene complexes at the active site of cytochrome P450 3A4: Evidence for a multiple substrate binding site
    • Dabrowski, M. J.; Schrag, M. L.; Wienkers, L. C.; Atkins, W. M. Pyrene.pyrene complexes at the active site of cytochrome P450 3A4: evidence for a multiple substrate binding site. J. Am. Chem. Soc. 2002, 124, 11866-11867.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 11866-11867
    • Dabrowski, M.J.1    Schrag, M.L.2    Wienkers, L.C.3    Atkins, W.M.4
  • 7
    • 2642555502 scopus 로고    scopus 로고
    • Effector-mediated alteration of substrate orientation in cytochrome P450 2C9
    • Hummel, M. A.; Gannett, P. M.; Aguilar, J. S.; Tracy, T. S. Effector-mediated alteration of substrate orientation in cytochrome P450 2C9. Biochemistry 2004, 43, 7207-7214.
    • (2004) Biochemistry , vol.43 , pp. 7207-7214
    • Hummel, M.A.1    Gannett, P.M.2    Aguilar, J.S.3    Tracy, T.S.4
  • 8
    • 0038691508 scopus 로고    scopus 로고
    • A method for determining two substrates binding in the same active site of cytochrome P450BM3: An explanation of high energy omega product formation
    • Rock, D. A.; Perkins, B. N.; Wahlstrom, J.; Jones, J. P. A method for determining two substrates binding in the same active site of cytochrome P450BM3: an explanation of high energy omega product formation. Arch. Biochem. Biophys. 2003, 416, 9-16.
    • (2003) Arch. Biochem. Biophys , vol.416 , pp. 9-16
    • Rock, D.A.1    Perkins, B.N.2    Wahlstrom, J.3    Jones, J.P.4
  • 9
    • 33646163913 scopus 로고    scopus 로고
    • Heteroactivator effects on the coupling and spin state equilibrium of CYP2C9
    • Locuson, C. W.; Gannett, P. M.; Tracy, T. S. Heteroactivator effects on the coupling and spin state equilibrium of CYP2C9. Arch. Biochem. Biophys. 2006, 449, 115-129.
    • (2006) Arch. Biochem. Biophys , vol.449 , pp. 115-129
    • Locuson, C.W.1    Gannett, P.M.2    Tracy, T.S.3
  • 11
    • 13444292821 scopus 로고    scopus 로고
    • Lansoprazole enantiomer activates human liver microsomal CYP2C9 catalytic activity in a stereospecific and substrate-specific manner
    • Liu, K. H.; Kim, M. J.; Jung, W. M.; Kang, W.; Cha, I. J.; Shin, J. G. Lansoprazole enantiomer activates human liver microsomal CYP2C9 catalytic activity in a stereospecific and substrate-specific manner. Drug Metab. Dispos. 2005, 33, 209-213.
    • (2005) Drug Metab. Dispos , vol.33 , pp. 209-213
    • Liu, K.H.1    Kim, M.J.2    Jung, W.M.3    Kang, W.4    Cha, I.J.5    Shin, J.G.6
  • 13
    • 0037048522 scopus 로고    scopus 로고
    • Pyrene.pyrene complexes at the active site of cytochrome P450 3A4: Evidence for a multiple substrate binding site
    • Dabrowski, M. J.; Schrag, M. L.; Wienkers, L. C.; Atkins, W. M. Pyrene.pyrene complexes at the active site of cytochrome P450 3A4: evidence for a multiple substrate binding site. J. Am. Chem. Soc. 2002, 124, 11866-11867.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 11866-11867
    • Dabrowski, M.J.1    Schrag, M.L.2    Wienkers, L.C.3    Atkins, W.M.4
  • 14
    • 2642555502 scopus 로고    scopus 로고
    • Effector-mediated alteration of substrate orientation in cytochrome P450 2C9
    • Hummel, M. A.; Gannett, P. M.; Aguilar, J. S.; Tracy, T. S. Effector-mediated alteration of substrate orientation in cytochrome P450 2C9. Biochemistry 2004, 43, 7207-7214.
    • (2004) Biochemistry , vol.43 , pp. 7207-7214
    • Hummel, M.A.1    Gannett, P.M.2    Aguilar, J.S.3    Tracy, T.S.4
  • 15
    • 0038691508 scopus 로고    scopus 로고
    • A method for determining two substrates binding in the same active site of cytochrome P450BM3: An explanation of high energy omega product formation
    • Rock, D. A.; Perkins, B. N.; Wahlstrom, J.; Jones, J. P. A method for determining two substrates binding in the same active site of cytochrome P450BM3: an explanation of high energy omega product formation. Arch. Biochem. Biophys. 2003, 416, 9-16.
    • (2003) Arch. Biochem. Biophys , vol.416 , pp. 9-16
    • Rock, D.A.1    Perkins, B.N.2    Wahlstrom, J.3    Jones, J.P.4
  • 16
    • 0036842029 scopus 로고    scopus 로고
    • Activation of CYP2C9-mediated metabolism by a series of dapsone analogs: Kinetics and structural requirements
    • Hutzler, J. M.; Kolwankar, D.; Hummel, M. A.; Tracy, T. S. Activation of CYP2C9-mediated metabolism by a series of dapsone analogs: kinetics and structural requirements. Drug Metab. Dispos. 2002, 30, 1194-1200.
    • (2002) Drug Metab. Dispos , vol.30 , pp. 1194-1200
    • Hutzler, J.M.1    Kolwankar, D.2    Hummel, M.A.3    Tracy, T.S.4
  • 17
    • 0036842029 scopus 로고    scopus 로고
    • Activation of CYP2C9-mediated metabolism by a series of dapsone analogs: Kinetics and structural requirements
    • Hutzler, J. M.; Kolwankar, D.; Hummel, M. A.; Tracy, T. S. Activation of CYP2C9-mediated metabolism by a series of dapsone analogs: kinetics and structural requirements. Drug Metab. Dispos. 2002, 30, 1194-1200.
    • (2002) Drug Metab. Dispos , vol.30 , pp. 1194-1200
    • Hutzler, J.M.1    Kolwankar, D.2    Hummel, M.A.3    Tracy, T.S.4
  • 19
    • 4143143372 scopus 로고    scopus 로고
    • The structure of human cytochrome P450 2C9 complexed with flurbiprofen at 2.0-A resolution
    • Wester, M. R.; Yano, J. K.; Schoch, G. A.; Yang, C.; Griffin, K. J.; Stout, C. D.; Johnson, E. F. The structure of human cytochrome P450 2C9 complexed with flurbiprofen at 2.0-A resolution. J. Biol. Chem. 2004, 279, 35630-35637.
    • (2004) J. Biol. Chem , vol.279 , pp. 35630-35637
    • Wester, M.R.1    Yano, J.K.2    Schoch, G.A.3    Yang, C.4    Griffin, K.J.5    Stout, C.D.6    Johnson, E.F.7
  • 20
    • 0026542989 scopus 로고
    • Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences
    • Gotoh, O. Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. J. Biol. Chem. 1992, 267, 83-90.
    • (1992) J. Biol. Chem , vol.267 , pp. 83-90
    • Gotoh, O.1
  • 21
    • 33748886840 scopus 로고    scopus 로고
    • Amiodarone analog-dependent effects on CYP2C9-mediated metabolism and kinetic profiles
    • Kumar, V.; Locuson, C. W.; Sham, Y. Y.; Tracy, T. S. Amiodarone analog-dependent effects on CYP2C9-mediated metabolism and kinetic profiles. Drug Metab. Dispos. 2006, 34, 1688-1696.
    • (2006) Drug Metab. Dispos , vol.34 , pp. 1688-1696
    • Kumar, V.1    Locuson, C.W.2    Sham, Y.Y.3    Tracy, T.S.4
  • 22
    • 24344435153 scopus 로고    scopus 로고
    • CYP2C-catalyzed delta9-tetrahydrocannabinol metabolism: Kinetics, pharmacogenetics and interaction with phenytoin
    • Bland, T. M.; Haining, R. L.; Tracy, T. S.; Gallery, P. S. CYP2C-catalyzed delta9-tetrahydrocannabinol metabolism: kinetics, pharmacogenetics and interaction with phenytoin. Biochem. Pharmacol. 2005, 70, 1096-1103.
    • (2005) Biochem. Pharmacol , vol.70 , pp. 1096-1103
    • Bland, T.M.1    Haining, R.L.2    Tracy, T.S.3    Gallery, P.S.4
  • 23
    • 33748802003 scopus 로고    scopus 로고
    • Structural basis for ligand promiscuity in cytochrome P450 3A4
    • Ekroos, M.; Sjogren, T. Structural basis for ligand promiscuity in cytochrome P450 3A4. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 13682-13687.
    • (2006) Proc. Natl. Acad. Sci. U.S.A , vol.103 , pp. 13682-13687
    • Ekroos, M.1    Sjogren, T.2
  • 24
    • 13844312649 scopus 로고    scopus 로고
    • ZINC-a free database of commercially available compounds for virtual screening
    • Irwin, J. J.; Shoichet, B. K. ZINC-a free database of commercially available compounds for virtual screening. J. Chem. Inf. Model. 2005, 45, 177-182.
    • (2005) J. Chem. Inf. Model , vol.45 , pp. 177-182
    • Irwin, J.J.1    Shoichet, B.K.2
  • 25
    • 0346963231 scopus 로고    scopus 로고
    • Direct interaction between substrates and endogenous steroids in the active site may change the activity of cytochrome P450 3A4
    • Torimoto, N.; Ishii, I.; Hata, M.; Nakamura, H.; Imada, H.; Ariyoshi, N.; Ohmori, S.; Igarashi, T.; Kitada, M. Direct interaction between substrates and endogenous steroids in the active site may change the activity of cytochrome P450 3A4. Biochemistry 2003, 42, 15068-15077.
    • (2003) Biochemistry , vol.42 , pp. 15068-15077
    • Torimoto, N.1    Ishii, I.2    Hata, M.3    Nakamura, H.4    Imada, H.5    Ariyoshi, N.6    Ohmori, S.7    Igarashi, T.8    Kitada, M.9
  • 26
    • 26744439941 scopus 로고
    • The crystal structure of a-pyridoin, 1,2-di-2-pyridylethenediol-1,2
    • Ashida, T.; Hirokawa, S. The crystal structure of a-pyridoin, 1,2-di-2-pyridylethenediol-1,2. Acta Crystallogr. 1965, 18, 122-127.
    • (1965) Acta Crystallogr , vol.18 , pp. 122-127
    • Ashida, T.1    Hirokawa, S.2
  • 27
    • 24744459452 scopus 로고    scopus 로고
    • Crystallographic study on the dioxygen complex of wild-type and mutant cytochrome P450cam. Implications for the dioxygen activation mechanism
    • Nagano, S.; Poulos, T. L. Crystallographic study on the dioxygen complex of wild-type and mutant cytochrome P450cam. Implications for the dioxygen activation mechanism. J. Biol. Chem. 2005, 280, 31659-31663.
    • (2005) J. Biol. Chem , vol.280 , pp. 31659-31663
    • Nagano, S.1    Poulos, T.L.2
  • 28
    • 0026542989 scopus 로고
    • Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences
    • Gotoh, O. Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. J. Biol. Chem. 1992, 267, 83-90.
    • (1992) J. Biol. Chem , vol.267 , pp. 83-90
    • Gotoh, O.1
  • 30
    • 0036206152 scopus 로고    scopus 로고
    • Polymorphic variants (CYP2C9*3 and CYP2C9*5) and the F114L active site mutation of CYP2C9: Effect on atypical kinetic metabolism profiles
    • Tracy, T. S.; Hutzler, J. M.; Haining, R. L.; Rettie, A. E.; Hummel, M. A.; Dickmann, L. J. Polymorphic variants (CYP2C9*3 and CYP2C9*5) and the F114L active site mutation of CYP2C9: effect on atypical kinetic metabolism profiles. Drug Metab. Dispos. 2002, 30, 385-390.
    • (2002) Drug Metab. Dispos , vol.30 , pp. 385-390
    • Tracy, T.S.1    Hutzler, J.M.2    Haining, R.L.3    Rettie, A.E.4    Hummel, M.A.5    Dickmann, L.J.6
  • 31
    • 13844312649 scopus 로고    scopus 로고
    • ZINC-a free database of commercially available compounds for virtual screening
    • Irwin, J. J.; Shoichet, B. K. ZINC-a free database of commercially available compounds for virtual screening. J. Chem. Inf. Model. 2005, 45, 177-182.
    • (2005) J. Chem. Inf. Model , vol.45 , pp. 177-182
    • Irwin, J.J.1    Shoichet, B.K.2
  • 32
    • 4143143372 scopus 로고    scopus 로고
    • The structure of human cytochrome P450 2C9 complexed with flurbiprofen at 2.0-A resolution
    • Wester, M. R.; Yano, J. K.; Schoch, G. A.; Yang, C.; Griffin, K. J.; Stout, C. D.; Johnson, E. F. The structure of human cytochrome P450 2C9 complexed with flurbiprofen at 2.0-A resolution. J. Biol. Chem. 2004, 279, 35630-35637.
    • (2004) J. Biol. Chem , vol.279 , pp. 35630-35637
    • Wester, M.R.1    Yano, J.K.2    Schoch, G.A.3    Yang, C.4    Griffin, K.J.5    Stout, C.D.6    Johnson, E.F.7
  • 35
    • 0003023614 scopus 로고
    • MOIL-View - A program for visualization of structure and dynamics of biomolecules and STO - A program for computing stochastic paths
    • Pullman, A, Ed, Kluwer: Netherlands
    • Simmerling, C.; Elber, R.; Zhang, J. MOIL-View - A program for visualization of structure and dynamics of biomolecules and STO - A program for computing stochastic paths. In Modeling of biomolecular structure and mechanisms; Pullman, A., Ed.; Kluwer: Netherlands, 1995; pp 241-265.
    • (1995) Modeling of biomolecular structure and mechanisms , pp. 241-265
    • Simmerling, C.1    Elber, R.2    Zhang, J.3
  • 36
    • 17144368025 scopus 로고    scopus 로고
    • Binding mode prediction of cytochrome p450 and thymidine kinase protein-ligand complexes by consideration of water and rescoring in automated docking
    • de Graaf, C.; Pospisil, P.; Pos, W.; Folkers, G.; Vermeulen, N. P. Binding mode prediction of cytochrome p450 and thymidine kinase protein-ligand complexes by consideration of water and rescoring in automated docking. J. Med. Chem. 2005, 48, 2308-2318.
    • (2005) J. Med. Chem , vol.48 , pp. 2308-2318
    • de Graaf, C.1    Pospisil, P.2    Pos, W.3    Folkers, G.4    Vermeulen, N.P.5
  • 37
    • 12144289984 scopus 로고    scopus 로고
    • Friesner, R. A.; Banks, J. L.; Murphy, R. B.; Halgren, T. A.; Klicic, J. J.; Mainz, D. T.; Repasky, M. P.; Knoll, E. H.; Shelley, M.; Perry, J. K.; Shaw, D. E.; Francis, P.; Shenkin, P. S. Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J. Med. Chem. 2004, 47, 1739-1749.
    • Friesner, R. A.; Banks, J. L.; Murphy, R. B.; Halgren, T. A.; Klicic, J. J.; Mainz, D. T.; Repasky, M. P.; Knoll, E. H.; Shelley, M.; Perry, J. K.; Shaw, D. E.; Francis, P.; Shenkin, P. S. Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J. Med. Chem. 2004, 47, 1739-1749.
  • 38
    • 4143143372 scopus 로고    scopus 로고
    • The structure of human cytochrome P450 2C9 complexed with flurbiprofen at 2.0-A resolution
    • Wester, M. R.; Yano, J. K.; Schoch, G. A.; Yang, C.; Griffin, K. J.; Stout, C. D.; Johnson, E. F. The structure of human cytochrome P450 2C9 complexed with flurbiprofen at 2.0-A resolution. J. Biol. Chem. 2004, 279, 35630-35637.
    • (2004) J. Biol. Chem , vol.279 , pp. 35630-35637
    • Wester, M.R.1    Yano, J.K.2    Schoch, G.A.3    Yang, C.4    Griffin, K.J.5    Stout, C.D.6    Johnson, E.F.7
  • 39
    • 0036842029 scopus 로고    scopus 로고
    • Activation of CYP2C9-mediated metabolism by a series of dapsone analogs: Kinetics and structural requirements
    • Hutzler, J. M.; Kolwankar, D.; Hummel, M. A.; Tracy, T. S. Activation of CYP2C9-mediated metabolism by a series of dapsone analogs: kinetics and structural requirements. Drug Metab. Dispos. 2002, 30, 1194-1200.
    • (2002) Drug Metab. Dispos , vol.30 , pp. 1194-1200
    • Hutzler, J.M.1    Kolwankar, D.2    Hummel, M.A.3    Tracy, T.S.4
  • 40
    • 4143143372 scopus 로고    scopus 로고
    • The structure of human cytochrome P450 2C9 complexed with flurbiprofen at 2.0-A resolution
    • Wester, M. R.; Yano, J. K.; Schoch, G. A.; Yang, C.; Griffin, K. J.; Stout, C. D.; Johnson, E. F. The structure of human cytochrome P450 2C9 complexed with flurbiprofen at 2.0-A resolution. J. Biol. Chem. 2004, 279, 35630-35637.
    • (2004) J. Biol. Chem , vol.279 , pp. 35630-35637
    • Wester, M.R.1    Yano, J.K.2    Schoch, G.A.3    Yang, C.4    Griffin, K.J.5    Stout, C.D.6    Johnson, E.F.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.