New clues arising from hunt of saccharides binding to galectin 3 via 3D QSAR and docking studies
Tài liệu tham khảo
Barondes, 1994, Galectins: a family of animal beta-galactoside-binding lectins, Cell, 76, 597, 10.1016/0092-8674(94)90498-7
Rabinovich, 2007, Functions of cell surface galectin-glycoprotein lattices, Curr Opin Struct Biol, 17, 513, 10.1016/j.sbi.2007.09.002
Piyush, 2017, Interaction of galectin-3 with MUC1 on cell surface promotes EGFR dimerization and activation in human epithelial cancer cells, Cell Death Differ, 24, 1937, 10.1038/cdd.2017.119
Chen, 2016, Pathological lymphangiogenesis is modulated by galectin-8-dependent crosstalk between podoplanin and integrin-associated VEGFR-3, Nat Commun, 7, 1
Funasaka, 2014, Galectin-3 in angiogenesis and metastasis, Glycobiology, 24, 886, 10.1093/glycob/cwu086
Nishi, 2007, Role of galectin-3 in human pulmonary fibrosis, Allergol Int, 56, 57, 10.2332/allergolint.O-06-449
Chou, 2018, Role of galectins in tumors and in clinical immunotherapy, Int J Mol Sci, 19, 430, 10.3390/ijms19020430
ClinicalTrialsgov
Liu, 2005, Rabinovich GA Galectins as modulators of tumour progression, Nat Rev Canc, 5, 29, 10.1038/nrc1527
Diaz-Alvarez, 2017, The many roles of galectin-3, a multifaceted molecule, in innate immune responses against pathogens, Mediat Inflamm, 1, 10.1155/2017/9247574
Dong, 2018, Galectin-3 as a novel biomarker for disease diagnosis and a target for therapy, Int J Mol Med, 41, 599
I Lala, 2015, Galectin-3 in heart failure pathology– “another brick in the wall”?, Acta Cardiol, 70, 323, 10.1080/AC.70.3.3080637
Meijers, 2015, Galectin-3 and post-myocardial infarction cardiac remodeling, Eur J Pharmacol, 763, 115, 10.1016/j.ejphar.2015.06.025
Saccon, 2017, Role of galectin-3 in autoimmune and non-autoimmune nephropathies, Autoimmun Rev, 16, 34, 10.1016/j.autrev.2016.09.023
Shin, 2013, The pleiotropic effects of galectin-3 in neuroinflammation: a review, Acta Histochem, 115, 407, 10.1016/j.acthis.2012.11.010
Hu, 2017, Galectin-3: a key player in arthritis, Joint Bone Spine, 84, 15, 10.1016/j.jbspin.2016.02.029
Giguere, 2008, Synthesis of stable and selective inhibitors of human galectins-1 and-3, Bioorg Med Chem, 16, 7811, 10.1016/j.bmc.2008.06.044
Zetterberg, 2018, Monosaccharide derivatives with low‐nanomolar lectin affinity and high selectivity based on combined fluorine–amide, phenyl–arginine, sulfur–π, and halogen bond interactions, ChemMedChem, 13, 133, 10.1002/cmdc.201700744
Delaine, 2016, Galectin‐3‐binding glycomimetics that strongly reduce bleomycin‐induced lung fibrosis and modulate intracellular glycan recognition, ChemBioChem, 17, 1759, 10.1002/cbic.201600285
Cumpstey, 2005, C2‐Symmetrical thiodigalactoside bis‐benzamido derivatives as high‐affinity inhibitors of galectin‐3: efficient lectin inhibition through double arginine–arene interactions, Angew Chem Int Ed, 44, 5110, 10.1002/anie.200500627
Roy, 2015
Dearden, 2017, The history and development of quantitative structure-activity relationships (QSARs). In Oncology: breakthroughs in research and practice, IGI Global, 67
Gramatica, 2020, Principles of QSAR modeling: comments and suggestions from personal experience, Int J Quant Struct Property Relat, 5, 1
Muratov, 2020, QSAR without borders, Chem Soc Rev, 49
Hansch, 1964, p-σ-π Analysis. A method for the correlation of biological activity and chemical structure, J Am Chem Soc, 86, 1616, 10.1021/ja01062a035
Ke, 2013, 3D‐QSAR‐assisted drug design: identification of a potent quinazoline‐based aurora kinase inhibitor, ChemMedChem, 8, 136, 10.1002/cmdc.201200464
Liu, 2019, In silico studies on potential TNKS inhibitors: a combination of pharmacophore and 3D-QSAR modelling, virtual screening, molecular docking and molecular dynamics, J Biomol Struct Dyn, 37, 3803, 10.1080/07391102.2018.1528887
Hoeglund, 2010, Optimization of a pipemidic acid autotaxin inhibitor, J Med Chem, 53, 1056, 10.1021/jm9012328
Chai, 2011, Identification of novel 5-hydroxy-1H-indole-3-carboxylates with anti-HBV activities based on 3D QSAR studies, J Mol Model, 17, 1831, 10.1007/s00894-010-0873-7
Jiao, 2010, Design, synthesis and anti-HIV integrase evaluation of N-(5-chloro-8-hydroxy-2-styrylquinolin-7-yl) benzenesulfonamide derivatives, Molecules, 15, 1903, 10.3390/molecules15031903
Verma, 2010, 3D-QSAR in drug design-a review, Curr Top Med Chem, 10, 95, 10.2174/156802610790232260
Sirois, 2006, A first QSAR model for galectin-3 glycomimetic inhibitors based on 3D docked structures, Med Chem, 2, 481, 10.2174/157340606778250252
Veerasamy, 2011, Validation of QSAR models-strategies and importance, Int J Drug Des Discov, 2, 511
Johannes, 2018, Galectins at a glance, J Cell Sci, 131, 1, 10.1242/jcs.208884
Tejler, 2007, Synthesis of galactose-mimicking 1H-(1, 2, 3-triazol-1-yl)-mannosides as selective galectin-3 and 9N inhibitors, Carbohydr Res, 342, 1869, 10.1016/j.carres.2007.03.012
Passeri, 2020, Strategies of virtual screening in medicinal chemistry, 194
Sethi, 2019, Molecular docking in modern drug discovery: principles and recent applications, 1
Dahlqvist, 2019, Aminopyrimidine–galactose hybrids are highly selective galectin-3 inhibitors, MedChemComm, 10, 913, 10.1039/C9MD00183B
Kumar, 2019, Structure and energetics of ligand–fluorine interactions with galectin‐3 backbone and side‐chain amides: insight into solvation effects and multipolar interactions, ChemMedChem, 14, 1528, 10.1002/cmdc.201900293
Stegmayr, 2019, Extracellular and intracellular small-molecule galectin-3 inhibitors, Sci Rep, 9, 1, 10.1038/s41598-019-38497-8
Kumar, 2019, Substituted polyfluoroaryl interactions with an arginine side chain in galectin-3 are governed by steric-, desolvation and electronic conjugation effects, Org Biomol Chem, 17, 1081, 10.1039/C8OB02888E
Peterson, 2018, Systematic tuning of fluoro-galectin-3 interactions provides thiodigalactoside derivatives with single-digit nM affinity and high selectivity, J Med Chem, 61, 1164, 10.1021/acs.jmedchem.7b01626
Dion, 2017, Development of a sensitive microarray platform for the ranking of galectin inhibitors: identification of a selective galectin‐3 inhibitor, ChemBioChem, 18, 2428, 10.1002/cbic.201700544
Atmanene, 2017, Biophysical and structural characterization of mono/di-arylated lactosamine derivatives interaction with human galectin-3, Biochem Biophys Res Commun, 489, 281, 10.1016/j.bbrc.2017.05.150
Rajput, 2016, A selective galactose–coumarin-derived galectin-3 inhibitor demonstrates involvement of galectin-3-glycan interactions in a pulmonary fibrosis model, J Med Chem, 59, 8141, 10.1021/acs.jmedchem.6b00957
Hsieh, 2016, Dual thio-digalactoside-binding modes of human galectins as the structural basis for the design of potent and selective inhibitors, Sci Rep, 6, 1, 10.1038/srep29457
Marchiori, 2015, Synthetic 1, 2, 3-triazole-linked glycoconjugates bind with high affinity to human galectin-3, Bioorg Med Chem, 23, 3414, 10.1016/j.bmc.2015.04.044
Rajput, 2014, Synthesis and evaluation of iminocoumaryl and coumaryl derivatized glycosides as galectin antagonists, Bioorg Med Chem Lett, 24, 3516, 10.1016/j.bmcl.2014.05.063
Van Hattum, 2013, Tuning the preference of thiodigalactoside-and lactosamine-based ligands to galectin-3 over galectin-1, J Med Chem, 56, 1350, 10.1021/jm301677r
Collins, 2012, Taloside inhibitors of galectin‐1 and galectin‐3, Chem Biol Drug Des, 79, 339, 10.1111/j.1747-0285.2011.01283.x
Oberg, 2011, Inhibition of galectins with small molecules, Chimia, 65, 18, 10.2533/chimia.2011.18
Oberg, 2011, Synthesis of 3-amido-3-deoxy-β-d-talopyranosides: all-cis-substituted pyranosides as lectin inhibitors, Tetrahedron, 67, 9164, 10.1016/j.tet.2011.09.098
Salameh, 2010, 1H-1, 2, 3-triazol-1-yl thiodigalactoside derivatives as high affinity galectin-3 inhibitors, Bioorg Med Chem, 18, 5367, 10.1016/j.bmc.2010.05.040
Tejler, 2009, Fragment-based development of triazole-substituted O-galactosyl aldoximes with fragment-induced affinity and selectivity for galectin-3, Org Biomol Chem, 7, 3982, 10.1039/b909091f
Oberg, 2008, Arginine binding motifs: design and synthesis of galactose-derived arginine tweezers as galectin-3 inhibitors, J Med Chem, 51, 2297, 10.1021/jm701266y
Cumpstey, 2008, Double affinity amplification of galectin–ligand interactions through arginine–arene interactions: synthetic, thermodynamic, and computational studies with aromatic diamido thiodigalactosides, Eur J Chem, 14, 4233, 10.1002/chem.200701932
Cumpstey, 2007, Studies of arginine–arene interactions through synthesis and evaluation of a series of galectin‐binding aromatic lactose esters, ChemBioChem, 8, 1389, 10.1002/cbic.200700040
Salameh, 2005, 3-(1, 2, 3-Triazol-1-yl)-1-thio-galactosides as small, efficient, and hydrolytically stable inhibitors of galectin-3, Bioorg Med Chem Lett, 15, 3344, 10.1016/j.bmcl.2005.05.084
Tejler, 2005, Synthesis of O-galactosyl aldoximes as potent LacNAc-mimetic galectin-3 inhibitors, Bioorg Med Chem Lett, 15, 2343, 10.1016/j.bmcl.2005.02.079
Sorme, 2005, Structural and thermodynamic studies on cation− π interactions in lectin− ligand complexes: high-affinity galectin-3 inhibitors through fine-tuning of an arginine− arene interaction, J Am Chem Soc, 127, 1737, 10.1021/ja043475p
Van Scherpenzeel, 2009, Synthesis and evaluation of new thiodigalactoside‐based chemical probes to label galectin‐3, ChemBioChem, 10, 1724, 10.1002/cbic.200900198
Waller, 1993, Three-dimensional QSAR of human immunodeficiency virus (I) protease inhibitors. 1. A CoMFA study employing experimentally-determined alignment rules, J Med Chem, 36, 4152, 10.1021/jm00078a003
Kim, 2015, Total synthesis and anticancer activity of novel Pulsatilla saponin D analogues, Chem Pharm Bull, 63, 669, 10.1248/cpb.c15-00106
Jung, 2004, Structure–activity relationship of oleanane disaccharides isolated from Akebia quinata versus cytotoxicity against cancer cells and NO inhibition, Biol Pharm Bull, 27, 744, 10.1248/bpb.27.744
Perez, 2008, Generation of new derivatives of the antitumor antibiotic mithramycin by altering the glycosylation pattern through combinatorial biosynthesis, ChemBioChem, 9, 2295, 10.1002/cbic.200800299
Roy, 2016, Be aware of error measures. Further studies on validation of predictive QSAR models, Chemometr Intell Lab Syst, 152, 18, 10.1016/j.chemolab.2016.01.008
Roy, 2017, How important is to detect systematic error in predictions and understand statistical applicability domain of QSAR models?, Chemometr Intell Lab Syst, 162, 44, 10.1016/j.chemolab.2017.01.010
Gadaleta, 2016, Applicability domain for QSAR models: where theory meets reality, Int J Quant Struct Property Relat, 1, 45, 10.4018/IJQSPR.2016010102
Roy, 2015, On a simple approach for determining applicability domain of QSAR models, Chemometr Intell Lab Syst, 145, 22, 10.1016/j.chemolab.2015.04.013