Nifuroxazide as JAK2 inhibitor: A binding mode proposal and Hel cell proliferation assay

European Journal of Pharmaceutical Sciences - Tập 162 - Trang 105822 - 2021
Marcela Oliveira Legramanti da Costa1, Thais Fernanda Amorim Pavani1, Angélica Nakagawa Lima2,3, Ana Lígia Scott2, Débora Felicia Vieira Ramos4, Mariana Lazarini4, Daniela Gonçales Galasse Rando1
1Grupo de Pesquisas Químico-Farmacêuticas, Departamento de Ciências Farmacêuticas, Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, Campus Diadema
2Laboratório de Biologia Computacional e Bioinformática, Universidade Federal do ABC
3Centro de Engenharia, Modelagem e Ciências Sociais Aplicadas, Universidade Federal do ABC
4Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, Campus Diadema

Tài liệu tham khảo

Abraham, 2015, Gromacs: High performance molecular simulations through multi-level parallelism from laptops to supercomputers, SoftwareX, 1–2, 19, 10.1016/j.softx.2015.06.001 Altman, 1976, Tetrazolium Salts and Formazans [Internet], 1 Amarego, 2000, 529 Andraos, 2012, Modulation of Activation-Loop Phosphorylation by JAK Inhibitors Is Binding Mode Dependent, Cancer Discov [Internet], 2, 512, 10.1158/2159-8290.CD-11-0324 Antonysamy, 2009, Fragment-based discovery of JAK-2 inhibitors, Bioorganic Med Chem Lett [Internet], 19, 279, 10.1016/j.bmcl.2008.08.064 Avila, 2010, Protein tyrosine kinases: challenges in the development of drugs aimed at cancer therapy, Rev Virtual Química [Internet], 2, 59 Bailly, 2019, Toward a repositioning of the antibacterial drug nifuroxazide for cancer treatment, Drug Discov Today [Internet], 24, 1930, 10.1016/j.drudis.2019.06.017 Baxter, 1998, Flexible docking using Tabu search and an empirical estimate of binding affinity, Proteins Struct Funct Genet, 33, 367, 10.1002/(SICI)1097-0134(19981115)33:3<367::AID-PROT6>3.0.CO;2-W Best, 2012, Optimization of the additive CHARMM all-atom protein force field targeting improved sampling of the backbone φ, ψ and side-chain χ1 and χ2 Dihedral Angles, J Chem Theory Comput, 8, 3257, 10.1021/ct300400x Bhullar, 2018, Kinase-targeted cancer therapies: Progress, challenges and future directions, Mol Cancer, 17, 1, 10.1186/s12943-018-0804-2 BUCKETT, 1964, Antibacterial properties of 5-nitro-2-furylglyoxylidene derivatives, J Pharm Pharmacol, 16, 663, 10.1111/j.2042-7158.1964.tb07385.x CARRON, 1963, Antiseptic properties of various 5-nitrofurylidene benzhydrazides. Study of (5-nitro-2-furfurylidene)-4-hydroxy-benzhydraxide, Ann Pharm Fr [Internet], 21, 287 Chekkara, 2014, Molecular docking studies of phenylaminopyrimidine and pyrazolylaminopyrimidine derivatives as Janus kinase 2 (JAK2) inhibitors, Int J Pharm Pharm Sci, 6, 225 2018 Dolinsky, 2004, PDB2PQR: An automated pipeline for the setup of Poisson-Boltzmann electrostatics calculations, Nucleic Acids Res, 32, 665, 10.1093/nar/gkh381 Fedorov, 2010, The (un) targeted cancer kinome, Nat Chem Biol [Internet], 6, 166, 10.1038/nchembio.297 Force, 2011, Cardiotoxicity of kinase inhibitors: The prediction and translation of preclinical models to clinical outcomes, Nat Rev Drug Discov [Internet], 10, 111, 10.1038/nrd3252 Frisch, 2009 Gavrin, 2013, Approaches to discover non-ATP site kinase inhibitors, Medchemcomm, 4, 41, 10.1039/C2MD20180A Grace T. Grace. Available from: http://plasma-gate.weizmann.ac.il/Grace/. (Acessed January 30, 2019). Hari, 2013, Sequence Determinants of a Specific Inactive Protein Kinase Conformation, Chem Biol [Internet], 20, 806, 10.1016/j.chembiol.2013.05.005 Hasinoff, 2010, The cardiotoxicity and myocyte damage caused by small molecule anticancer tyrosine kinase inhibitors is correlated with lack of target specificity, Toxicol Appl Pharmacol [Internet], 244, 190, 10.1016/j.taap.2009.12.032 Hu, 2019, Discovery and evaluation of ZT55, a novel highly-selective tyrosine kinase inhibitor of JAK2 V617F against myeloproliferative neoplasms, J Exp Clin Cancer Res, 38, 1, 10.1186/s13046-019-1062-x Humphrey, 1996, VMD: Visual molecular dynamics, J Mol Graph [Internet], 14, 33, 10.1016/0263-7855(96)00018-5 Jo, 2008, A web-based graphical user interface for CHARMM, J Comput Chem [Internet], 29, 1859, 10.1002/jcc.20945 Jones, 1997, Development and Validation of a Genetic Algorithm for Flexible Docking, JMolBiol, 267, 727 Jorgensen, 1983, Comparison of simple potential functions for simulating liquid water, J Chem Phys, 79, 926, 10.1063/1.445869 Karłowicz-Bodalska, 2019, Safety of oral nifuroxazide - analysis of data from a spontaneous reporting system, Acta Pol Pharm - Drug Res, 76, 745 Kiss, 2009, Identification of a novel inhibitor of JAK2 tyrosine kinase by structure-based virtual screening, Bioorg Med Chem Lett [Internet], 19, 3598, 10.1016/j.bmcl.2009.04.138 Kitchen DB, Decornez H, Furr JR, Bajorath J. DOCKING AND SCORING IN VIRTUAL SCREENING FOR DRUG DISCOVERY : METHODS AND APPLICATIONS. 2004;3(November). Kong, 2017, How Does the L884P Mutation Confer Resistance to Type-II Inhibitors of JAK2 Kinase : A Comprehensive Molecular Modeling Study, Sci Rep [Internet], 7, 1 Landau, 2008, Dynamic equilibrium between multiple active and inactive conformations explains regulation and oncogenic mutations in ErbB receptors, Biochim Biophys Acta - Rev Cancer [Internet], 1785, 12, 10.1016/j.bbcan.2007.08.001 Li, 2016, Enhancing specificity in the Janus kinases: A study on the thienopyridine JAK2 selective mechanism combined molecular dynamics simulation, Mol Biosyst, 12, 575, 10.1039/C5MB00747J Li, 2016, Insights into DFG-in and DFG-out JAK2 binding modes for a rational strategy of type II inhibitors combined computational study, RSC Adv [Internet]., 6, 45540, 10.1039/C6RA06266K Liu, 1997, Mechanism of cellular 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) reduction, J Neurochem, 69, 581, 10.1046/j.1471-4159.1997.69020581.x Lu, 2020, New Promise and Opportunities for Allosteric Kinase Inhibitors, Angew Chemie - Int Ed, 59, 13764, 10.1002/anie.201914525 Lucet, 2006, The structural basis of Janus kinase 2 inhibition by a potent and specific pan-Janus kinase inhibitor, Blood, 107, 176, 10.1182/blood-2005-06-2413 Müller, 2015, The ins and outs of selective kinase inhibitor development, Nat Chem Biol [Internet], 11, 818, 10.1038/nchembio.1938 Nelson, 2008, Nifuroxazide inhibits survival of multiple myeloma cells by directly inhibiting STAT3, Blood, 112, 5095, 10.1182/blood-2007-12-129718 P. Pauli, 2018, Structural Characteristics of Protein Kinases and Their Inhibitors in Clinical Use, Rev Virtual Química [Internet], 10, 1280, 10.21577/1984-6835.20180088 Peterson, 2018, 5-Nitrofurans and Cancer: Teaching an Old Drug New Tricks, Cell Chem Biol [Internet], 25, 1439, 10.1016/j.chembiol.2018.12.005 Rando, 2002, Potential tuberculostatic agents. Topliss application on benzoic acid [(5-Nitro-thiophen-2-yl)-methylene]-hydrazide series, Bioorganic Med Chem, 10, 10.1016/S0968-0896(01)00313-3 Rando, 2008, Antileishmanial activity screening of 5-nitro-2-heterocyclic benzylidene hydrazides, Bioorganic Med Chem, 16, 6724, 10.1016/j.bmc.2008.05.076 Rando, 2019, Vanillin-Retaled N-Acylhydrazones: Synthesis, Antischistosomal Properties and Target Fishing Studies, Curr Top Med Chem, 19, 1241, 10.2174/1568026619666190620163237 Roskoski, 2016, Janus kinase (JAK) inhibitors in the treatment of inflammatory and neoplastic diseases, Pharmacol Res [Internet], 111, 784, 10.1016/j.phrs.2016.07.038 Sarvi, 2018, ALDH1 Bio-activates Nifuroxazide to Eradicate ALDHHigh Melanoma-Initiating Cells, Cell Chem Biol [Internet], 25, 1456, 10.1016/j.chembiol.2018.09.005 Stark, 2012, The JAK-STAT Pathway at Twenty, Immunity [Internet], 36, 503, 10.1016/j.immuni.2012.03.013 Stewart, 1989, Optimization of parameters for semiempirical methods I. Applications, J Comput Chem [Internet], 10, 209, 10.1002/jcc.540100208 Stewart, 1989, Optimization of parameters for semiempirical methods II. Applications, J Comput Chem [Internet], 10, 221, 10.1002/jcc.540100209 The PyMOL Molecular Graphics System. Schrödinger, LLC. Thomé, 2016, Ratiometric analysis of Acridine Orange staining in the study of acidic organelles and autophagy, J Cell Sci, 129, 4622 Vainchenker, 2018, JAK inhibitors for the treatment of myeloproliferative neoplasms and other disorders, F1000Research [Internet], 7, 82, 10.12688/f1000research.13167.1 Yang, 2015, Nifuroxazide induces apoptosis and impairs pulmonary metastasis in breast cancer model, Cell Death Dis, 6, 10.1038/cddis.2015.63 Yang, 2017, Binding of hydroxylated polybrominated diphenyl ethers with human serum albumin: Spectroscopic characterization and molecular modeling, Luminescence, 32, 978, 10.1002/bio.3280 Ye, 2017, Inhibition of Stat3 signaling pathway by nifuroxazide improves antitumor immunity and impairs colorectal carcinoma metastasis, Cell Death Dis [Internet], 8 Yeh, 1999, The Janus kinase family of protein tyrosine kinases and their role in signaling, Cell Mol Life Sci, 55, 1523, 10.1007/s000180050392 Zhu, 2016, Nifuroxazide exerts potent anti-tumor and anti-metastasis activity in melanoma, Sci Rep [Internet], 6, 20253, 10.1038/srep20253