Design, computational studies, synthesis and biological evaluation of thiazole-based molecules as anticancer agents
Tài liệu tham khảo
Abraham, 2015, GROMACS: High performance molecular simulations through multi-level parallelism from laptops to supercomputers, 19
Akl, 2014, A dual role for the anti-apoptotic Bcl-2 protein in cancer: mitochondria versus endoplasmic reticulum, Biochim. Biophys. Acta (BBA) – Mol. Cell Res., 1843, 2240, 10.1016/j.bbamcr.2014.04.017
Ali, 2015, Heterocyclic scaffolds: centrality in anticancer drug development, Curr. Drug Targets, 16, 711, 10.2174/1389450116666150309115922
Ayalew, 2017, Conjugation of paclitaxel to hybrid peptide carrier and biological evaluation in Jurkat and A549 cancer cell lines, ACS Med. Chem. Lett., 8, 814, 10.1021/acsmedchemlett.7b00117
Ayati, 2015, Recent applications of 1, 3-thiazole core structure in the identification of new lead compounds and drug discovery, Eur. J. Med. Chem., 97, 699, 10.1016/j.ejmech.2015.04.015
Azmi, 2011, Emerging Bcl-2 inhibitors for the treatment of cancer, Expert Opin. Emerg. Drugs, 16, 59, 10.1517/14728214.2010.515210
Baell, 2010, New substructure filters for removal of pan assay interference compounds (PAINS) from screening libraries and for their exclusion in bioassays, J. Med. Chem., 53, 2719, 10.1021/jm901137j
Bartocci, 2016, Computational modeling, formal analysis, and tools for systems biology, PLoS Comput. Biol., 12, 10.1371/journal.pcbi.1004591
Berendsen, 1981, Interaction models for water in relation to protein hydration, 331
Berman, 2000, The protein data bank, Nucleic Acids Res., 28, 235, 10.1093/nar/28.1.235
Biswas, 2018, Drug development and bioanalytical method validation for a novel anticancer molecule, 4‐(dimethylamino)‐2‐(p‐tolylamino) thiazole‐5‐carbonitrile, Drug Dev. Res., 79, 391, 10.1002/ddr.21462
Bodur, 2012, Bcl-2 inhibitors: emerging drugs in cancer therapy, Curr. Med. Chem., 19, 1804, 10.2174/092986712800099839
Bussi, 2007, Canonical sampling through velocity rescaling, J. Chem. Phys., 126, 10.1063/1.2408420
Chen, 2000, Distinct stages of cytochrome c release from mitochondria: evidence for a feedback amplification loop linking caspase activation to mitochondrial dysfunction in genotoxic stress induced apoptosis, Cell Death Differ., 7, 227, 10.1038/sj.cdd.4400629
Darzynkiewicz, 1997, Cytometry in cell necrobiology: analysis of apoptosis and accidental cell death (necrosis), Cytometry, 27, 1, 10.1002/(SICI)1097-0320(19970101)27:1<1::AID-CYTO2>3.0.CO;2-L
Duran-Frigola, 2013, Structural systems pharmacology: the role of 3D structures in next-generation drug development, Chem. Biol., 20, 674, 10.1016/j.chembiol.2013.03.004
Essmann, 1995, A smooth particle mesh Ewald method, J. Chem. Phys., 103, 8577, 10.1063/1.470117
Ferrao, 2015, Cellular and phenotypic plasticity in cancer, Front. Oncol., 5, 171, 10.3389/fonc.2015.00171
Ferreira, 2015, Molecular docking and structure-based drug design strategies, Molecules, 20, 13384, 10.3390/molecules200713384
Fleming, 2010, Nitrile-containing pharmaceuticals: efficacious roles of the nitrile pharmacophore, J. Med. Chem., 53, 7902, 10.1021/jm100762r
Frenzel, 2009, Bcl2 family proteins in carcinogenesis and the treatment of cancer, Apoptosis, 14, 584, 10.1007/s10495-008-0300-z
Garattini, 1997, Are me-too drugs justified, J. Nephrol., 10, 283
Goodsell, 2015, The RCSB PDB “molecule of the month”: inspiring a molecular view of biology, PLoS Biol., 13, 10.1371/journal.pbio.1002140
Harder, 2015, OPLS3: a force field providing broad coverage of drug-like small molecules and proteins, J. Chem. Theory Comput., 12, 281, 10.1021/acs.jctc.5b00864
Hess, 1997, LINCS: a linear constraint solver for molecular simulations, J. Comput. Chem., 18, 1463, 10.1002/(SICI)1096-987X(199709)18:12<1463::AID-JCC4>3.0.CO;2-H
Hodgkins, 1956, The synthesis of isothiocyanates from amines, J. Org. Chem., 21, 404, 10.1021/jo01110a006
Homeyer, 2012, Free energy calculations by the molecular mechanics Poisson− Boltzmann surface area method, Mol. Inf., 31, 114, 10.1002/minf.201100135
Huber, 2014, Heteroaromatic π-stacking energy landscapes, J. Chem. Inf. Model., 54, 1371, 10.1021/ci500183u
Huigsloot, 2002, Differential regulation of doxorubicin-induced mitochondrial dysfunction and apoptosis by Bcl-2 in mammary adenocarcinoma (MTLn3) cells, J. Biol. Chem., 277, 35869, 10.1074/jbc.M200378200
Kumari, 2014, g_mmpbsa A GROMACS tool for high-throughput MM-PBSA calculations, J. Chem. Inf. Model., 54, 1951, 10.1021/ci500020m
Lama, 2008, Anti-apoptotic Bcl-XL protein in complex with BH3 peptides of pro-apoptotic Bak, bad, and Bim proteins: comparative molecular dynamics simulations, Proteins: Struct., Funct., Bioinf., 73, 492, 10.1002/prot.22075
Leoni, 2014, Novel thiazole derivatives: a patent review (2008–2012; part 1), Expert Opin. Ther. Pat., 24, 201, 10.1517/13543776.2014.858121
Leung, 1999, Differential effects of chemotherapeutic agents on the Bcl-2/Bax apoptosis pathway in human breast cancer cell line MCF-7, Breast Cancer Res. Treat., 55, 73, 10.1023/A:1006190802590
Liu, 2014, Niclosamide inhibits androgen receptor variants expression and overcomes enzalutamide resistance in castration resistant prostate cancer, Clin. Cancer Res., 3296
Lu, 2011, Design, synthesis, and SAR studies of 4-substituted methoxylbenzoyl-aryl-thiazoles analogues as potent and orally bioavailable anticancer agents, J. Med. Chem., 54, 4678, 10.1021/jm2003427
Lu, 2017, Anticancer drug development, getting out from bottleneck, Med. Chem., 7, 739, 10.4172/2161-0444.1000423
Malde, 2011, An automated force field topology builder (ATB) and repository: version 1.0, J. Chem. Theory Comput., 7, 4026, 10.1021/ct200196m
Nogrady, 2005
Ntie-Kang, 2013, An in silico evaluation of the ADMET profile of the StreptomeDB database, Springer Plus, 2, 353, 10.1186/2193-1801-2-353
Oancea, 2006, Apoptosis assays, 279
Palchaudhuri, 2015, A small molecule that induces intrinsic pathway apoptosis with unparalleled speed, Cell Rep., 13, 2027, 10.1016/j.celrep.2015.10.042
Pang, 2012, Bak conformational changes induced by ligand binding: insight into BH3 domain binding and Bak homo-oligomerization, Sci. Rep., 2, 257, 10.1038/srep00257
Parrinello, 1981, Polymorphic transitions in single crystals: a new molecular dynamics method, J. Appl. Phys., 52, 7182, 10.1063/1.328693
Perini, 2018, BCL-2 as therapeutic target for hematological malignancies, J. Hematol. Oncol., 11, 65, 10.1186/s13045-018-0608-2
Petros, 2004, Structural biology of the Bcl-2 family of proteins, Biochimica et Biophysica Acta (BBA)-Molecular Cell Research, 1644, 83, 10.1016/j.bbamcr.2003.08.012
Pettersen, 2004, UCSF chimera—a visualization system for exploratory research and analysis, J. Comput. Chem., 25, 1605, 10.1002/jcc.20084
Rajappa, 1982, A general synthesis of thiazoles. Part 4. Synthesis of 5-acyl-2, 4-diaminothiazoles, J. Chem. Sci., 91, 441, 10.1007/BF02864180
Rastelli, 2010, Fast and accurate predictions of binding free energies using MM-PBSA and MM-GBSA, J. Comput. Chem., 31, 797
Romagnoli, 2012, Synthesis and biological evaluation of 2-substituted-4-(3′, 4′, 5′-trimethoxyphenyl)-5-aryl thiazoles as anticancer agents, Bioorg. Med. Chem., 20, 7083, 10.1016/j.bmc.2012.10.001
Schmid, 2011, Definition and testing of the GROMOS force-field versions 54A7 and 54B7, Eur. Biophys. J., 40, 843, 10.1007/s00249-011-0700-9
Schwede, 2003, SWISS-MODEL: an automated protein homology-modeling server, Nucleic Acids Res., 31, 3381, 10.1093/nar/gkg520
Sharifi, 2015, Doxorubicin changes Bax/Bcl-xL ratio, caspase-8 and 9 in breast cancer cells, Adv. Pharm. Bull., 5, 351, 10.15171/apb.2015.049
Singh, 2016, Prediction of anticancer molecules using hybrid model developed on molecules screened against NCI-60 cancer cell lines, BMC Cancer, 16, 77, 10.1186/s12885-016-2082-y
Sleebs, 2013, Discovery of potent and selective benzothiazole hydrazone inhibitors of Bcl-XL, J. Med. Chem., 56, 5514, 10.1021/jm400556w
Souers, 2013, ABT-199, a potent and selective BCL-2 inhibitor, achieves antitumor activity while sparing platelets, Nat. Med., 19, 202, 10.1038/nm.3048
Stroet, 2018, The automated topology builder version 3.0 (ATB3. 0): prediction of solvation free enthalpies in water and hexane, J. Chem. Theory Comput., 14, 5834, 10.1021/acs.jctc.8b00768
T Chhabria, 2016, Thiazole: a review on chemistry, synthesis and therapeutic importance of its derivatives, Curr. Top. Med. Chem., 16, 2841, 10.2174/1568026616666160506130731
Touré, 2013, The role of the acidity of N-heteroaryl sulfonamides as inhibitors of Bcl-2 family protein–protein interactions, ACS Med. Chem. Lett., 4, 186, 10.1021/ml300321d
Toure, 2013, The role of the acidity of N-heteroaryl sulfonamides as inhibitors of bcl-2 family protein interactions, ACS Med. Chem. Lett., 4, 186, 10.1021/ml300321d
Wang, 2017, Anti-migration and anti-invasion thiazole analogs for treatment of cellular proliferative disease
Weis, 2006, Ligand affinities predicted with the MM/PBSA method: dependence on the simulation method and the force field, J. Med. Chem., 49, 6596, 10.1021/jm0608210
Xu, 2016, Identification of small-molecule inhibitors of Zika virus infection and induced neural cell death via a drug repurposing screen, Nat. Med., 22, 1101, 10.1038/nm.4184