98
Views
12
CrossRef citations to date
0
Altmetric
Original Research

In silico identification of EGFR-T790M inhibitors with novel scaffolds: start with extraction of common features

, , , , , , & show all
Pages 789-839 | Published online: 14 Aug 2013

References

  • Shimizu N Behzadian MA Shimizu Y Genetics of cell surface receptors for bioactive polypeptides: binding of epidermal growth factor is associated with the presence of human chromosome 7 in human-mouse cell hybrids Proc Natl Acad Sci U S A 1980 77 6 3600 3604 6968072
  • Schlessinger J Cell signaling by receptor tyrosine kinases Cell 2000 103 2 211 225 11057895
  • Yarden Y Sliwkowski MX Untangling the ErbB signalling network Nat Rev Mol Cell Biol 2001 2 2 127 137 11252954
  • Zhou W Ercan D Chen L Novel mutant-selective EGFR kinase inhibitors against EGFR T790M Nature 2009 462 7276 1070 1074 20033049
  • Carmi C Cavazzoni A Vezzosi S Novel irreversible epidermal growth factor receptor inhibitors by chemical modulation of the cysteine-trap portion J Med Chem 2010 53 5 2038 2050 20151670
  • Bai F Liu H Tong L Discovery of novel selective inhibitors for EGFR-T790M/L858R Bioorg Med Chem Lett 2012 22 3 1365 1370 22227214
  • Li S Guo C Sun X Synthesis and biological evaluation of quinazoline and quinoline bearing 2,2,6,6-tetramethylpiperidine-N-oxyl as potential epidermal growth factor receptor(EGFR) tyrosine kinase inhibitors and EPR bio-probe agents Eur J Med Chem 2012 49 271 278 22309911
  • Sato T Watanabe H Tsuganezawa K Identification of novel drug-resistant EGFR mutant inhibitors by in silico screening using comprehensive assessments of protein structures Bioorg Med Chem 2012 20 12 3756 3767 22607878
  • Salomon DS Brandt R Ciardiello F Normanno N Epidermal growth factor-related peptides and their receptors in human malignancies Crit Rev Oncol Hematol 1995 19 3 183 232 7612182
  • Roskoski R The ErbB/HER receptor protein-tyrosine kinases and cancer Biochem Biophys Res Commun 2004 319 1 1 11 15158434
  • Gazdar AF Activating and resistance mutations of EGFR in non-small-cell lung cancer: role in clinical response to EGFR tyrosine kinase inhibitors Oncogene 2009 28 Suppl 1 S24 S31 19680293
  • Lemmon MA Schlessinger J Cell signaling by receptor tyrosine kinases Cell 2010 141 7 1117 1134 20602996
  • Lurje G Lenz HJ EGFR signaling and drug discovery Oncology 2009 77 6 400 410 20130423
  • Hynes NE Lane HA ERBB receptors and cancer: the complexity of targeted inhibitors Nat Rev Cancer 2005 5 5 341 354 15864276
  • Doebele RC Oton AB Peled N Camidge DR Bunn PA New strategies to overcome limitations of reversible EGFR tyrosine kinase inhibitor therapy in non-small cell lung cancer Lung Cancer 2010 69 1 1 12 20092908
  • Sequist LV Second-generation epidermal growth factor receptor tyrosine kinase inhibitors in non-small cell lung cancer Oncologist 2007 12 3 325 330 17405897
  • Yun CH Mengwasser KE Toms AV The T790M mutation in EGFR kinase causes drug resistance by increasing the affinity for ATP Proc Natl Acad Sci U S A 2008 105 6 2070 2075 18227510
  • Schneider MR Wolf E The epidermal growth factor receptor ligands at a glance J Cell Physiol 2009 218 3 460 466 19006176
  • Lupberger J Zeisel MB Xiao F EGFR and EphA2 are host factors for hepatitis C virus entry and possible targets for antiviral therapy Nat Med 2011 17 5 589 595 21516087
  • Spicer JF Rudman SM EGFR inhibitors in non-small cell lung cancer (NSCLC): the emerging role of the dual irreversible EGFR/HER2 inhibitor BIBW 2992 Target Oncol 2010 5 4 245 255 20574858
  • Rocha-Lima CM Soares HP Raez LE Singal R EGFR targeting of solid tumors Cancer Control 2007 14 3 295 304 17615536
  • Okamoto I Epidermal growth factor receptor in relation to tumor development: EGFR-targeted anticancer therapy FEBS J 2010 277 2 309 315 19922468
  • Ciardiello F Tortora G EGFR antagonists in cancer treatment New Engl J Med 2008 358 11 1160 1174 18337605
  • Kobayashi S Ji H Yuza Y An alternative inhibitor overcomes resistance caused by a mutation of the epidermal growth factor receptor Cancer Res 2005 65 16 7096 7101 16103058
  • Greulich H Chen TH Feng W Oncogenic transformation by inhibitor-sensitive and -resistant EGFR mutants PLoS Med 2005 2 11 e313 16187797
  • Riely GJ Second-generation epidermal growth factor receptor tyrosine kinase inhibitors in non-small cell lung cancer J Thorac Oncol 2008 3 6 Suppl 2 S146 S149 18520300
  • Liu B Bernard B Wu JH Impact of EGFR point mutations on the sensitivity to gefitinib: insights from comparative structural analyses and molecular dynamics simulations Proteins 2006 65 2 331 346 16927343
  • Wissner A Mansour TS The development of HKI-272 and related compounds for the treatment of cancer Arch Pharm (Weinheim) 2008 341 8 465 477 18493974
  • Li D Ambrogio L Shimamura T BIBW2992, an irreversible EGFR/HER2 inhibitor highly effective in preclinical lung cancer models Oncogene 2008 27 34 4702 4711 18408761
  • Engelman JA Zejnullahu K Gale CM PF00299804, an irreversible pan-ERBB inhibitor, is effective in lung cancer models with EGFR and ERBB2 mutations that are resistant to gefitinib Cancer Res 2007 67 24 11924 11932 18089823
  • Kwak EL Sordella R Bell DW Irreversible inhibitors of the EGF receptor may circumvent acquired resistance to gefitinib Proc Natl Acad Sci U S A 2005 102 21 7665 7670 15897464
  • Godin-Heymann N Ulkus L Brannigan BW The T790M “gatekeeper” mutation in EGFR mediates resistance to low concentrations of an irreversible EGFR inhibitor Mol Cancer Ther 2008 7 4 874 879 18413800
  • Blair JA Rauh D Kung C Structure-guided development of affinity probes for tyrosine kinases using chemical genetics Nat Chem Biol 2007 3 4 229 238 17334377
  • Tsou HR Overbeek-Klumpers EG Hallett WA Optimization of 6,7-disubstituted-4-(arylamino)quinoline-3-carbonitriles as orally active, irreversible inhibitors of human epidermal growth factor receptor-2 kinase activity J Med Chem 2005 48 4 1107 1131 15715478
  • Wissner A Overbeek E Reich MF Synthesis and structure-activity relationships of 6,7-disubstituted 4-anilinoquinoline-3-carbonitriles. The design of an orally active, irreversible inhibitor of the tyrosine kinase activity of the epidermal growth factor receptor (EGFR) and the human epidermal growth factor receptor-2 (HER-2) J Med Chem 2003 46 1 49 63 12502359
  • Wissner A Brawner Floyd MB Rabindran SK Syntheses and EGFR and HER-2 kinase inhibitory activities of 4-anilinoquinoline-3-carbonitriles: analogues of three important 4-anilinoquinazolines currently undergoing clinical evaluation as therapeutic antitumor agents Bioorg Med Chem Lett 2002 12 20 2893 2897 12270171
  • Tsou HR Mamuya N Johnson BD 6-Substituted-4-(3-bromophenylamino)quinazolines as putative irreversible inhibitors of the epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor (HER-2) tyrosine kinases with enhanced ant-itumor activity J Med Chem 2001 44 17 2719 2734 11495584
  • Marvin http://www.chemaxon.com [computer program] Version 5.6.0.1 ChemAxon Ltd 2011
  • Halgren TA Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94 J Comput Chem 1996 17 5–6 490 519
  • Gaussian 03 [computer program] Version Revision C.02 Wallingford CT Gaussian, Inc 2004
  • Yang W Mortier WJ The use of global and local molecular parameters for the analysis of the gas-phase basicity of amines J Am Chem Soc 1986 108 19 5708 5711 22175316
  • Boström J Reproducing the conformations of protein-bound ligands: a critical evaluation of several popular conformational searching tools J Comput Aided Mol Des 2001 15 12 1137 1152 12160095
  • Discovery Studio Modeling Environment [computer program] Version Release 3.1 San Diego Accelrys Software Inc 2012
  • Michalczyk A Klüter S Rode HB Structural insights into how irreversible inhibitors can overcome drug resistance in EGFR Bioorg Med Chem 2008 16 7 3482 3488 18316192
  • FRED program http://www.eyesopen.com [computer program] Version Version 2.2.5 OpenEye Scientific Software Inc Santa Fe, NM, USA 2012
  • Nicholls A Grant JA Brown FK Gaussian docking functions Biopolymers 2003 68 1 76 90 12579581
  • Verkhivker GM Bouzida D Gehlhaar DK Deciphering common failures in molecular docking of ligand-protein complexes J Comput Aided Mol Des 2000 14 8 731 751 11131967
  • Eldridge MD Murray CW Auton TR Paolini GV Mee RP 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 5 425 445 9385547
  • Stahl M Rarey M Detailed analysis of scoring functions for virtual screening J Med Chem 2001 44 7 1035 1042 11297450
  • Grant JA Pickup BT Nicholls A A smooth permittivity function for Poisson-Boltzmann solvation methods J Comput Chem 2001 22 6 608 640
  • Traxler P Furet P Strategies toward the design of novel and selective protein tyrosine kinase inhibitors Pharmacol Ther 1999 82 2–3 195 206 10454197
  • Cavasotto CN Ortiz MA Abagyan RA Piedrafita FJ In silico identification of novel EGFR inhibitors with antiproliferative activity against cancer cells Bioorg Med Chem Lett 2006 16 7 1969 1974 16413185
  • Rode HB Sos ML Grütter C Heynck S Simard JR Rauh D Synthesis and biological evaluation of 7-substituted-1-(3-bromophenylamino) isoquinoline-4-carbonitriles as inhibitors of myosin light chain kinase and epidermal growth factor receptor Bioorg Med Chem 2011 19 1 429 439 21130659
  • Dror O Shulman-Peleg A Nussinov R Wolfson HJ Predicting molecular interactions in silico: I. A guide to pharmacophore identification and its applications to drug design Curr Med Chem 2004 11 1 71 90 14754427
  • Güner OF History and evolution of the pharmacophore concept in computer-aided drug design Curr Top Med Chem 2002 2 12 1321 1332 12470283
  • Xiang M Cao Y Fan W Chen L Mo Y Computer-aided drug design: lead discovery and optimization Comb Chem High Throughput Screen 2012 15 4 328 337 22221065
  • Davis AM Teague SJ Kleywegt GJ Application and limitations of X-ray crystallographic data in structure-based ligand and drug design Angew Chem Int Ed Engl 2003 42 24 2718 2736 12820253
  • Tuccinardi T Docking-based virtual screening: recent developments Comb Chem High Throughput Screen 2009 12 3 303 314 19275536
  • Plewczynski D Łazniewski M von Grotthuss M Rychlewski L Ginalski K VoteDock: consensus docking method for prediction of protein-ligand interactions J Comput Chem 2011 32 4 568 581 20812324
  • Schapira M Abagyan R Totrov M Nuclear hormone receptor targeted virtual screening J Med Chem 2003 46 14 3045 3059 12825943
  • Ravindranathan KP Mandiyan V Ekkati AR Bae JH Schlessinger J Jorgensen WL Discovery of novel fibroblast growth factor receptor 1 kinase inhibitors by structure-based virtual screening J Med Chem 2010 53 4 1662 1672 20121196

References

  • Wissner A Brawner Floyd MB Rabindran Sridhar K Syntheses and EGFR and HER-2 kinase inhibitory activities of 4-anilinoquinoline-3-carbonitriles: analogues of three important 4-anilinoquinazolines currently undergoing clinical evaluation as therapeutic antitumor agents Bioorg Med Chem Lett 2002 12 20 2893 2897 12270171
  • Wissner A Overbeek E Reich MF Synthesis and Structure-Activity Relationships of 6,7-Disubstituted 4-Anilinoquinoline-3-carbonitriles. The Design of an Orally Active, Irreversible Inhibitor of the Tyrosine Kinase Activity of the Epidermal Growth Factor Receptor (EGFR) and the Human Epidermal Growth Factor Receptor-2 (HER-2) J Med Chem 2003 46 1 49 63 12502359
  • Tsou H-R Overbeek-Klumpers EG Hallett WA Optimization of 6,7-disubstituted-4-(arylamino)quinoline-3-carbonitriles as orally active, irreversible inhibitors of human epidermal growth factor receptor-2 kinase activity J Med Chem 2005 48 4 1107 1131 15715478
  • Tsou H-R Mamuya N Johnson BD 6-Substituted-4-(3-bromophenylamino)quinazolines as Putative Irreversible Inhibitors of the Epidermal Growth Factor Receptor (EGFR) and Human Epidermal Growth Factor Receptor (HER-2) Tyrosine Kinases with Enhanced Antitumor Activity J Med Chem 2001 44 17 2719 2734 11495584

References

  • Wissner A Brawner Floyd MB Rabindran Sridhar K Syntheses and EGFR and HER-2 kinase inhibitory activities of 4-anilinoquinoline-3-carbonitriles: analogues of three important 4-anilinoquinazolines currently undergoing clinical evaluation as therapeutic antitumor agents Bioorg Med Chem Lett 2002 12 20 2893 2897 12270171
  • Wissner A Overbeek E Reich MF Synthesis and Structure-Activity Relationships of 6,7-Disubstituted 4-Anilinoquinoline-3-carbonitriles. The Design of an Orally Active, Irreversible Inhibitor of the Tyrosine Kinase Activity of the Epidermal Growth Factor Receptor (EGFR) and the Human Epidermal Growth Factor Receptor-2 (HER-2) J Med Chem 2003 46 1 49 63 12502359
  • Tsou H-R Overbeek-Klumpers EG Hallett WA Optimization of 6,7-disubstituted-4-(arylamino)quinoline-3-carbonitriles as orally active, irreversible inhibitors of human epidermal growth factor receptor-2 kinase activity J Med Chem 2005 48 4 1107 1131 15715478
  • Tsou H-R Mamuya N Johnson BD 6-Substituted-4-(3-bromophenylamino)quinazolines as Putative Irreversible Inhibitors of the Epidermal Growth Factor Receptor (EGFR) and Human Epidermal Growth Factor Receptor (HER-2) Tyrosine Kinases with Enhanced Antitumor Activity J Med Chem 2001 44 17 2719 2734 11495584
  • Zhou W Ercan D Chen L Novel mutant-selective EGFR kinase inhibitors against EGFR T790M Nature 2009 462 7276 1070 1074 20033049

References