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Original Research

Combining structure-based pharmacophore modeling, virtual screening, and in silico ADMET analysis to discover novel tetrahydro-quinoline based pyruvate kinase isozyme M2 activators with antitumor activity

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Pages 1195-1210 | Published online: 02 Sep 2014

References

  • Christofk HR Vander Heiden MG Wu N Pyruvate kinase M2 is a phosphotyrosine-binding protein Nature 2008 452 181 186 18337815
  • Chaneton B Gottlieb E Rocking cell metabolism: revised functions of the key glycolytic regulator PKM2 in cancer Trends Biochem Sci 2012 37 309 316 22626471
  • Christofk HR Vander Heiden MG Harris MH The M2 splice isoform of pyruvate kinase is important for cancer metabolism and tumour growth Nature 2008 452 230 233 18337823
  • Altenberg B Greulich KO Genes of glycolysis are ubiquitously overexpressed in 24 cancer classes Genomics 2004 84 1014 1020 15533718
  • Warburg O On the origin of cancer cells Science 1956 123 309 314 13298683
  • Hsu PP Sabatini DM Cancer cell metabolism: Warburg and beyond Cell 2008 134 703 707 18775299
  • Tamada M Suematsu M Saya H Pyruvate Kinase M2: Multiple Faces for Conferring Benefits on Cancer Cells Clin Cancer Res 2012 18 5554 5561 23071357
  • Ye J Mancuso A Tong X Pyruvate kinase M2 promotes de novo serine synthesis to sustain mTORC1 activity and cell proliferation Proc Natl Acad Sci 2012 109 6904 6909 22509023
  • Lv L Li D Zhao D Acetylation targets the M2 isoform of pyruvate kinase for degradation through chaperone-mediated autophagy and promotes tumor growth Mol Cell 2011 42 719 730 21700219
  • Dombrauckas JD Santarsiero BD Mesecar AD Structural basis for tumor pyruvate kinase M2 allosteric regulation and catalysis Biochemistry 2005 44 9417 9429 15996096
  • Takenaka M Noguchi T Sadahiro S Isolation and characterization of the human pyruvate kinase M gene Eur J Biochem 1991 198 101 106 2040271
  • Cheong H Lu C Lindsten T Therapeutic targets in cancer cell metabolism and autophagy Nat Biotech 2012 30 1 8
  • Yamada K Noguchi T Regulation of pyruvate kinase M gene expression Biochem Biophys Res Commun 1999 256 257 262 10079172
  • DeBerardinis RJ Sayed N Ditsworth D Brick by brick: metabolism and tumor cell growth Curr Opin Genet Dev 2008 18 54 61 18387799
  • Anastasiou D Yu Y Israelsen WJ Pyruvate kinase M2 activators promote tetramer formation and suppress tumorigenesis Nat Chem Biol 2012 8 839 847 22922757
  • Boxer MB Jiang JK Vander Heiden MG Evaluation of substituted N,N’-diarylsulfonamides as activators of the tumor cell specific M2 isoform of pyruvate kinase J Med Chem 2010 53 1048 1055 20017496
  • Jiang JK Boxer MB Vander Heiden MG Evaluation of thieno[3,2-b]pyrrole[3,2-d]pyridazinones as activators of the tumor cell specific M2 isoform of pyruvate kinase Bioorg Med Chem Lett 2010 20 3387 3393 20451379
  • Walsh MJ Brimacombe KR Veith H 2-Oxo-N-aryl-1,2,3,4-tetrahydroquinoline-6-sulfonamides as activators of the tumor cell specific M2 isoform of pyruvate kinase Bioorg Med Chem Lett 2011 21 6322 6327 21958545
  • Xu Y Liu XH Saunders M Discovery of 3-(trifluoromethyl)-1-H-pyrazole-5-carboxamide activators of the M2 isoform of pyruvate kinase (PKM2) Bioorg Med Chem Lett 2014 24 515 519 24374270
  • Guo C Linton A Jalaie M Discovery of 2-((1H-benzo[d] imidazol-1-yl)methyl)-4H-pyrido[1,2-a]pyrimidin-4-ones as novel PKM2 activators Bioorg Med Chem Lett 2013 23 3358 3363 23622982
  • Chen ZJ Jiang QL He G Multicomplex-Based Pharmacophore and QSAR of Aryl-Sulfamides as Pyruvate Kinase M2 Activators Acta Phys Chim Sin 2013 29 1793 1803
  • He G Qiu M Li R Multicomplex-based pharmacophore-guided 3D-QSAR studies of N-substituted 2′-(aminoaryl)benzothiazoles as Aurora-A inhibitors Chem Biol Drug Des 2012 79 960 971 22381081
  • Ouyang L He G Huang W Combined Structure-Based Pharmacophore and 3D-QSAR Studies on Phenylalanine Series Compounds as TPH1 Inhibitors Int J Mol Sci 2012 13 5348 5363 22754301
  • Li B Zhou R He G Molecular Docking, QSAR and Molecular Dynamics Simulation on Spiro-oxindoles as MDM2 Inhibitors Acta Chim Sin 2013 71 1396 1403
  • Wu F Xu T He G Discovery of novel focal adhesion kinase inhibitors using a hybrid protocol of virtual screening approach based on multicomplex-based pharmacophore and molecular docking Int J Mol Sci 2012 13 15668 15678 23443087
  • Peng F Peng A Luo Y Combined structure-based pharmacophore, virtual screening, and 3D-QSAR studies of structural diverse dehydrosqualene synthase inhibitors Med Chem Res 2013 22 4858 4866
  • Liu C He G Jiang Q Novel Hybrid Virtual Screening Protocol Based on Molecular Docking and Structure-Based Pharmacophore for Discovery of Methionyl-tRNA Synthetase Inhibitors as Antibacterial Agents Int J Mol Sci 2013 14 14225 14239 23839093
  • Ouyang L Huang Y Zhao Y Preparation, antibacterial evaluation and preliminary structure-activity relationship (SAR) study of benzothiazol- and benzoxazol-2-amine derivatives Bioorg Med Chem Lett 2012 22 3044 3049 22494615
  • Zhong H Huang W He G Molecular dynamics simulation of tryptophan hydroxylase-1: binding modes and free energy analysis to phenylalanine derivative inhibitors Int J Mol Sci 2013 14 9947 9962 23665899
  • Berman HM Westbrook J Feng Z The protein data bank Nucl Acid Res 2000 28 235 242
  • Zou J Xie HZ Yang SY Towards more accurate pharmacophore modeling: multicomplex-based comprehensive pharmacophore map and most frequent-feature pharmacophore model of CDK2 J Mol Graph Model 2008 27 430 438 18786843
  • Discovery Studio, version 35 Accelrys Inc San Diego, CA, USA 2012
  • Irwin JJ Sterling T Mysinger MM ZINC: A Free Tool to Discover Chemistry for Biology J Chem Inf Model 2012 52 1757 1768 22587354
  • Irwin JJ Shoichet BK ZINC-a free database of commercially available compounds for virtual screening J Chem Inf Model 2005 45 177 182 15667143
  • Xiang ML Lei K Fan WJ In silico identification of EGFR-T790M inhibitors with novel scaffolds: start with extraction of common features Drug Des Devel Ther 2013 7 789 839
  • Alam S Khan F QSAR and docking studies on xanthone derivatives for anticancer activity targeting DNA topoisomerase IIα Drug Des Devel Ther 2014 8 183 195
  • Yadav DK Meena A Srivastava A Development of QSAR model for immunomodulatory activity of natural coumarinolignoids Drug Des Devel Ther 2010 4 173 186
  • Laskowski RA Swindells MB LigPlot+: multiple ligand-protein interaction diagrams for drug discovery J Chem Inf Model 2011 51 2778 2786 21919503
  • Luo M Wang XS Roth BL Golbraikh A Tropsha A Application of Quantitative Structure–Activity Relationship Models of 5-HT1A Receptor Binding to Virtual Screening Identifies Novel and Potent 5-HT1A Ligands J Chem Inf Model 2014 54 634 647 24410373
  • Enslein K Blake BW Borgstedt HH Prediction of probability of carcinogenicity for a set of ongoing NTP bioassays Mutagenesis 1990 5 305 306 2398815
  • Chaudhaery SS Roy KK Saxena AK Consensus Superiority of the Pharmacophore-Based Alignment, Over Maximum Common Substructure (MCS): 3D-QSAR Studies on Carbamates as Acetylcholinesterase Inhibitors J Chem Inf Model 2009 49 1590 1601 19441865
  • Roth BL Baner K Westkaemper R Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist Proc Natl Acad Sci U S A 2002 99 11934 11939 12192085