메뉴 건너뛰기




Volumn 54, Issue 12, 2011, Pages 4006-4017

Structure-based design of potent aromatase inhibitors by high-throughput docking

Author keywords

[No Author keywords available]

Indexed keywords

AOP 13801200; AOP 13848083; AROMATASE INHIBITOR; BAS 00665638; BAS 00782664; BAS 02077837; BAS 05399144; BAS 11404029; BAS 11404034; BAS 12378719; BAS 12756136; BAS 12914183; BAS 12914671; BAS 12914683; BAS 12927218; BAS 15369430; LEG 13848093; LEG 21508414; LEG 22473243; SYN 15645644; SYN 15645717; SYN 17475691; SYN 19577078; SYN 19990642; SYN 19994888; SYN 19999063; SYN 20028567; SYN 22987768; SYN 23725844; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 79959410458     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2000689     Document Type: Article
Times cited : (98)

References (47)
  • 2
    • 33847796753 scopus 로고    scopus 로고
    • Aromatase inhibitors: Structural features and biochemical characterization
    • DOI 10.1196/annals.1386.022, Estrogens and Human Diseases
    • Hong, Y.; Chen, S. Aromatase inhibitors: structural features and biochemical characterization Ann. N.Y. Acad. Sci. 2006, 1089, 237-251 (Pubitemid 47092077)
    • (2006) Annals of the New York Academy of Sciences , vol.1089 , pp. 237-251
    • Hong, Y.1    Chen, S.2
  • 3
    • 48049086830 scopus 로고    scopus 로고
    • Aromatase inhibitors: Past, present and future in breast cancer therapy
    • Dutta, U.; Pant, K. Aromatase inhibitors: past, present and future in breast cancer therapy Med. Oncol. 2008, 25, 113-124
    • (2008) Med. Oncol. , vol.25 , pp. 113-124
    • Dutta, U.1    Pant, K.2
  • 4
    • 58149339806 scopus 로고    scopus 로고
    • Structural basis for androgen specificity and oestrogen synthesis in human aromatase
    • Ghosh, D.; Griswold, J.; Erman, M.; Pangborn, W. Structural basis for androgen specificity and oestrogen synthesis in human aromatase Nature 2009, 457, 219-223
    • (2009) Nature , vol.457 , pp. 219-223
    • Ghosh, D.1    Griswold, J.2    Erman, M.3    Pangborn, W.4
  • 6
    • 59449087748 scopus 로고    scopus 로고
    • Fast three dimensional pharmacophore virtual screening of new potent non-steroid aromatase inhibitors
    • Neves, M. A.; Dinis, T. C.; Colombo, G.; Sá e Melo, M. L. Fast three dimensional pharmacophore virtual screening of new potent non-steroid aromatase inhibitors J. Med. Chem. 2009, 52, 143-150
    • (2009) J. Med. Chem. , vol.52 , pp. 143-150
    • Neves, M.A.1    Dinis, T.C.2    Colombo, G.3    Sá Melo, M.L.4
  • 7
    • 67651154131 scopus 로고    scopus 로고
    • An efficient steroid pharmacophore-based strategy to identify new aromatase inhibitors
    • Neves, M. A.; Dinis, T. C.; Colombo, G.; Sá e Melo, M. L. An efficient steroid pharmacophore-based strategy to identify new aromatase inhibitors Eur. J. Med. Chem. 2009, 44, 4121-4127
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 4121-4127
    • Neves, M.A.1    Dinis, T.C.2    Colombo, G.3    Sá Melo, M.L.4
  • 9
    • 47249136040 scopus 로고    scopus 로고
    • Non-steroidal aromatase inhibitors based on a biphenyl scaffold: Synthesis, in vitro SAR, and molecular modelling
    • Jackson, T.; Woo, L. W.; Trusselle, M. N.; Purohit, A.; Reed, M. J.; Potter, B. V. L. Non-steroidal aromatase inhibitors based on a biphenyl scaffold: synthesis, in vitro SAR, and molecular modelling ChemMedChem 2008, 3) 603-618
    • (2008) ChemMedChem , Issue.3 , pp. 603-618
    • Jackson, T.1    Woo, L.W.2    Trusselle, M.N.3    Purohit, A.4    Reed, M.J.5    Potter, B.V.L.6
  • 10
    • 3242884966 scopus 로고    scopus 로고
    • High-throughput docking as a source of novel drug leads
    • DOI 10.1016/j.cbpa.2004.05.001, PII S1367593104000729
    • Alvarez, J. C. High-throughput docking as a source of novel drug leads Curr. Opin. Chem. Biol. 2004, 8, 365-370 (Pubitemid 38993729)
    • (2004) Current Opinion in Chemical Biology , vol.8 , Issue.4 , pp. 365-370
    • Alvarez, J.C.1
  • 11
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • DOI 10.1016/S0169-409X(96)00423-1, PII S0169409X96004231
    • Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug. Delivery Rev. 1997, 23, 3-25 (Pubitemid 27046991)
    • (1997) Advanced Drug Delivery Reviews , vol.23 , Issue.1-3 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 12
    • 33644836657 scopus 로고    scopus 로고
    • Three-dimensional model of the human aromatase enzyme and density functional parameterization of the iron-containing protoporphyrin IX for a molecular dynamics study of heme-cysteinato cytochromes
    • DOI 10.1002/prot.20829
    • Favia, A. D.; Cavalli, A.; Masetti, M.; Carotti, A.; Recanatini, M. Three-dimensional model of the human aromatase enzyme and density functional parameterization of the iron-containing protoporphyrin IX for a molecular dynamics study of heme-cysteinato cytochromes Proteins 2006, 62, 1074-1087 (Pubitemid 43364170)
    • (2006) Proteins: Structure, Function and Genetics , vol.62 , Issue.4 , pp. 1074-1087
    • Favia, A.D.1    Cavalli, A.2    Masetti, M.3    Carotti, A.4    Recanatini, M.5
  • 13
    • 34547692960 scopus 로고    scopus 로고
    • A three-dimensional model of CYP19 aromatase for structure-based drug design
    • DOI 10.1016/j.jsbmb.2006.11.023, PII S0960076007001021
    • Karkola, S.; Höltje, H. D.; Wähälä, K. J. A three-dimensional model of CYP19 aromatase for structure-based drug design Steroid Biochem. Mol. Biol. 2007, 105, 63-70 (Pubitemid 47211957)
    • (2007) Journal of Steroid Biochemistry and Molecular Biology , vol.105 , Issue.1-5 , pp. 63-70
    • Karkola, S.1    Holtje, H.-D.2    Wahala, K.3
  • 14
    • 20544475681 scopus 로고    scopus 로고
    • Docking versus pharmacophore model generation: A comparison of high-throughput virtual screening strategies for the search of human rhinovirus coat protein inhibitors
    • DOI 10.1002/qsar.200430929
    • Steindl, T.; Langer, T. Docking versus pharmacophore model generation: a comparison of high-throughput virtual screening strategies for the search of human rhinovirus coat protein inhibitors QSAR Comb. Sci. 2005, 24, 470-479 (Pubitemid 40846439)
    • (2005) QSAR and Combinatorial Science , vol.24 , Issue.4 , pp. 470-479
    • Steindl, T.1    Langer, T.2
  • 16
    • 51849126692 scopus 로고    scopus 로고
    • Schrödinger LLC: New York
    • Schrödinger; Schrödinger LLC: New York, 2005; http://www.schrodinger.com.
    • (2005) Schrödinger
  • 18
    • 0031226772 scopus 로고    scopus 로고
    • Empirical scoring functions: I. The development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes
    • Eldridge, M. D.; Murray, C. W.; Auton, T. R.; Paolini, G. V.; Mee, R. P. Empirical scoring functions: I. The development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes J. Comput.-Aided Mol. Des. 1997, 11, 425-445 (Pubitemid 127505895)
    • (1997) Journal of Computer-Aided Molecular Design , vol.11 , Issue.5 , pp. 425-445
    • Eldridge, M.D.1    Murray, C.W.2    Auton, T.R.3    Paolini, G.V.4    Mee, R.P.5
  • 19
    • 0035658264 scopus 로고    scopus 로고
    • BindingDB: A web-accessible molecular recognition database
    • Chen, X.; Liu, M.; Gilson, M. K. Binding DB: a web-accessible molecular recognition database. Comb. Chem. High Throughput Screening 2001, 4, 719-725; http://www.bindingdb.org (accessed May 5, 2009). (Pubitemid 34003162)
    • (2001) Combinatorial Chemistry and High Throughput Screening , vol.4 , Issue.8 , pp. 719-725
    • Chen, X.1    Liu, M.2    Gilson, M.K.3
  • 21
    • 3042645255 scopus 로고    scopus 로고
    • Computer-assisted design of selective imidazole inhibitors for cytochrome P450 enzymes
    • DOI 10.1021/jm030608t
    • Verras, A.; Kuntz, I. D.; Ortiz de Montellano, P. R. Computer-assisted design of selective imidazole inhibitors for cytochrome p450 enzymes J. Med. Chem. 2004, 47, 3572-3579 (Pubitemid 38822018)
    • (2004) Journal of Medicinal Chemistry , vol.47 , Issue.14 , pp. 3572-3579
    • Verras, A.1    Kuntz, I.D.2    Ortiz De Montellano, P.R.3
  • 23
    • 0035025191 scopus 로고    scopus 로고
    • DOCK 4.0: Search strategies for automated molecular docking of flexible molecule databases
    • DOI 10.1023/A:1011115820450
    • Ewing, T. J.; Makino, S.; Skillman, A. G.; Kuntz, I. D. DOCK 4.0: search strategies for automated molecular docking of flexible molecule databases J. Comput.-Aided Mol. Des. 2001, 15, 411-428 (Pubitemid 32452109)
    • (2001) Journal of Computer-Aided Molecular Design , vol.15 , Issue.5 , pp. 411-428
    • Ewing, T.J.A.1    Makino, S.2    Skillman, A.G.3    Kuntz, I.D.4
  • 24
    • 0031552362 scopus 로고    scopus 로고
    • Development and validation of a genetic algorithm for flexible docking
    • DOI 10.1006/jmbi.1996.0897
    • Jones, G.; Willett, P.; Glen, R. C.; Leach, A. R.; Taylor, R. Development and validation of a genetic algorithm for flexible docking J. Mol. Biol. 1997, 267, 727-748 (Pubitemid 27170693)
    • (1997) Journal of Molecular Biology , vol.267 , Issue.3 , pp. 727-748
    • Jones, G.1    Willett, P.2    Glen, R.C.3    Leach, A.R.4    Taylor, R.5
  • 25
    • 79959411230 scopus 로고    scopus 로고
    • Asinex Ltd: Moscow
    • Asinex; Asinex Ltd: Moscow; http://www.asinex.com.
    • Asinex
  • 26
    • 0019835546 scopus 로고
    • Inhibitors of cytochrome P-450s and their mechanism of action
    • Testa, B.; Jenner, P. Inhibitors of cytochrome P-450s and their mechanism of action Drug Metab. Rev. 1981, 12, 1-117 (Pubitemid 12208842)
    • (1981) Drug Metabolism Reviews , vol.12 , Issue.1 , pp. 1-117
    • Testa, B.1    Jenner, P.2
  • 28
    • 0029044427 scopus 로고
    • Pyridyl-substituted tetrahydrocyclopropa[a]naphthalenes: Highly active and selective inhibitors of P450 arom
    • Hartmann, R. W.; Bayer, H.; Grün, G.; Sergejew, T.; Bartz, U.; Mitrenga, M. Pyridyl-substituted tetrahydrocyclopropa[a]naphthalenes: highly active and selective inhibitors of P450 arom J. Med. Chem. 1995, 38, 2103-2111
    • (1995) J. Med. Chem. , vol.38 , pp. 2103-2111
    • Hartmann, R.W.1    Bayer, H.2    Grün, G.3    Sergejew, T.4    Bartz, U.5    Mitrenga, M.6
  • 29
    • 0017687255 scopus 로고
    • Steric factors in the inhibitory interaction of imidazoles with microsomal enzymes
    • DOI 10.1016/0006-2952(77)90241-6
    • Rogerson, T. D.; Wilkinson, C. F.; Hetarski, K. Steric factors in the inhibitory interaction of imidazoles with microsomal enzymes Biochem. Pharmacol. 1977, 26, 1039-1042 (Pubitemid 8107444)
    • (1977) Biochemical Pharmacology , vol.26 , Issue.11 , pp. 1039-1042
    • Rogerson, T.D.1    Wilkinson, C.F.2    Hetarski, K.3
  • 31
    • 42949169980 scopus 로고    scopus 로고
    • Identification of Plasmodium falciparum spermidine synthase active site binders through structure-based virtual screening
    • DOI 10.1021/jm7016144
    • Jacobsson, M.; Gäredal, M.; Schultz, J.; Karlén, A. Identification of Plasmodium falciparum spermidine synthase active site binders through structure-based virtual screening J. Med. Chem. 2008, 51, 2777-2786 (Pubitemid 351620799)
    • (2008) Journal of Medicinal Chemistry , vol.51 , Issue.9 , pp. 2777-2786
    • Jacobsson, M.1    Garedal, M.2    Schultz, J.3    Karlen, A.4
  • 33
    • 33646854265 scopus 로고    scopus 로고
    • Structure of microsomal cytochrome P450 2B4 complexed with the antifungal drug bifonazole: Insight into P450 conformational plasticity and membrane interaction
    • DOI 10.1074/jbc.M511464200
    • Zhao, Y.; White, M. A.; Muralidhara, B. K.; Sun, L.; Halpert, J. R.; Stout, C. D. Structure of microsomal cytochrome P450 2B4 complexed with the antifungal drug bifonazole: insight into P450 conformational plasticity and membrane interaction J. Biol. Chem. 2006, 281, 5973-5981 (Pubitemid 43847698)
    • (2006) Journal of Biological Chemistry , vol.281 , Issue.9 , pp. 5973-5981
    • Zhao, Y.1    White, M.A.2    Muralidhara, B.K.3    Sun, L.4    Halpert, J.R.5    Stout, C.D.6
  • 35
    • 0034819384 scopus 로고    scopus 로고
    • Evaluation of the mechanism of aromatase cytochrome p450 A site-directed mutagenesis study
    • DOI 10.1046/j.1432-1327.2001.01886.x
    • Kao, Y. C.; Korzekwa, K. R.; Laughton, C. A.; Chen, S. Evaluation of the mechanism of aromatase cytochrome P450. A site-directed mutagenesis study Eur. J. Biochem. 2001, 268, 243-251 (Pubitemid 32867307)
    • (2001) European Journal of Biochemistry , vol.268 , Issue.2 , pp. 243-251
    • Kao, Y.-C.1    Korzekwa, K.R.2    Laughton, C.A.3    Chen, S.4
  • 36
    • 0030013560 scopus 로고    scopus 로고
    • Binding characteristics of seven inhibitors of human aromatase: A site- directed mutagenesis study
    • Kao, Y. C.; Cam, L. L.; Laughton, C. A.; Zhou, D.; Chen, S. Binding characteristics of seven inhibitors of human aromatase: a site-directed mutagenesis study Cancer Res. 1996, 56, 3451-3460 (Pubitemid 26251636)
    • (1996) Cancer Research , vol.56 , Issue.15 , pp. 3451-3460
    • Kao, Y.-C.1    Cam, L.L.2    Laughton, C.A.3    Zhou, D.4    Chen, S.5
  • 39
    • 0023583624 scopus 로고
    • Crystal structures of metyrapone- and phenylimidazole-inhibited complexes of cytochrome P-450(cam)
    • Poulos, T. L.; Howard, A. J. Crystal structures of metyrapone- and phenylimidazole-inhibited complexes of cytochrome P-450cam Biochemistry 1987, 26, 8165-8174 (Pubitemid 18023065)
    • (1987) Biochemistry , vol.26 , Issue.25 , pp. 8165-8174
    • Poulos, T.L.1    Howard, A.J.2
  • 41
    • 77956417807 scopus 로고    scopus 로고
    • Bicyclic derivatives of the potent dual aromatase-steroid sulfatase inhibitor 2-bromo-4-{[(4-cyanophenyl)(4 H -1,2,4-triazol-4-yl)amino]methyl} phenylsulfamate: Synthesis, SAR, crystal structure, and in vitro and in vivo activities
    • Wood, P. M.; Woo, L. W.; Labrosse, J. R.; Thomas, M. P.; Mahon, M. F.; Chander, S. K.; Purohit, A.; Reed, M. J.; Potter, B. V. L. Bicyclic derivatives of the potent dual aromatase-steroid sulfatase inhibitor 2-bromo-4-{[(4- cyanophenyl)(4 H -1,2,4-triazol-4-yl)amino]methyl}phenylsulfamate: synthesis, SAR, crystal structure, and in vitro and in vivo activities ChemMedChem. 2010, 5) 1577-1593
    • (2010) ChemMedChem. , Issue.5 , pp. 1577-1593
    • Wood, P.M.1    Woo, L.W.2    Labrosse, J.R.3    Thomas, M.P.4    Mahon, M.F.5    Chander, S.K.6    Purohit, A.7    Reed, M.J.8    Potter, B.V.L.9
  • 42
    • 77955324216 scopus 로고    scopus 로고
    • Design, synthesis, and biological evaluation of resveratrol analogues as aromatase and quinone reductase 2 inhibitors for chemoprevention of cancer
    • Sun, B.; Hoshino, J.; Jermihov, K.; Marler, L.; Pezzuto, J. M.; Mesecar, A. D.; Cushman, M. Design, synthesis, and biological evaluation of resveratrol analogues as aromatase and quinone reductase 2 inhibitors for chemoprevention of cancer Bioorg. Med. Chem. 2010, 18, 5352-5366
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 5352-5366
    • Sun, B.1    Hoshino, J.2    Jermihov, K.3    Marler, L.4    Pezzuto, J.M.5    Mesecar, A.D.6    Cushman, M.7
  • 43
    • 77649196704 scopus 로고    scopus 로고
    • Discovery of novel fibroblast growth factor receptor 1 kinase inhibitors by structure-based virtual screening
    • Ravindranathan, K. P.; Mandiyan, V.; Ekkati, A. R.; Bae, J. H.; Schlessinger, J.; Jorgensen, W. L. Discovery of novel fibroblast growth factor receptor 1 kinase inhibitors by structure-based virtual screening J. Med. Chem. 2010, 53, 1662-1672
    • (2010) J. Med. Chem. , vol.53 , pp. 1662-1672
    • Ravindranathan, K.P.1    Mandiyan, V.2    Ekkati, A.R.3    Bae, J.H.4    Schlessinger, J.5    Jorgensen, W.L.6
  • 44
    • 77957894400 scopus 로고    scopus 로고
    • CoCoCo: A free suite of multiconformational chemical databases for high-throughput virtual screening purposes
    • (release 2010)
    • Del Rio, A.; Barbosa, A. J.; Caporuscio, F.; Mangiatordi, G. F. CoCoCo: a free suite of multiconformational chemical databases for high-throughput virtual screening purposes. Mol. Biosyst. 2010, 6, 2122-2128; http://www.cococo-database.it (release 2010).
    • (2010) Mol. Biosyst. , vol.6 , pp. 2122-2128
    • Del Rio, A.1    Barbosa, A.J.2    Caporuscio, F.3    Mangiatordi, G.F.4
  • 45
    • 79959458958 scopus 로고    scopus 로고
    • Molecular Networks GmbH-Computerchemie, Erlangen, Germany
    • Molecular Networks: Inspiring Chemical Discovery; Molecular Networks GmbH-Computerchemie, Erlangen, Germany; http://www.molecular-networks.com.
    • Molecular Networks: Inspiring Chemical Discovery
  • 46
    • 31444452744 scopus 로고
    • Automatic generation of 3D-atomic coordinates for organic molecules
    • Gasteiger, J.; Rudolph, C.; Sadowski, J. Automatic generation of 3D-atomic coordinates for organic molecules Tetrahedron Comput. Methods 1990, 3, 537-547
    • (1990) Tetrahedron Comput. Methods , vol.3 , pp. 537-547
    • Gasteiger, J.1    Rudolph, C.2    Sadowski, J.3
  • 47
    • 0011859785 scopus 로고    scopus 로고
    • GraphPad Software: San Diego, CA
    • GraphPad Software; GraphPad Software: San Diego, CA; www.graphpad.com.
    • GraphPad Software


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.