Synthesis, Molecular Docking, Molecular Dynamics, DFT and Antimicrobial Activity Studies of 5-substituted-2-(p-methylphenyl)benzoxazole Derivatives

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dc.authoridCelik, Ismail/0000-0002-8146-1663
dc.authoridcelik, ismail/0000-0002-8146-1663
dc.authorwosidCelik, Ismail/ABE-5813-2021
dc.authorwosidcelik, ismail/AAX-3221-2020
dc.contributor.authorErol, Meryem
dc.contributor.authorCelik, Ismail
dc.contributor.authorKuyucuklu, Gulcan
dc.date.accessioned2024-06-12T10:54:23Z
dc.date.available2024-06-12T10:54:23Z
dc.date.issued2021
dc.departmentTrakya Üniversitesien_US
dc.description.abstractIn this study, new 2-(p-methylphenyl)-5-(2-substitutedacetamido)benzoxazole derivatives were synthesized, and antimicrobial activities on six bacteria and their twelve drug-resistant isolates and one fungus and its two drug-resistant isolates were investigated by microdilution method. B1 against Staphylococcus aureus isolate, and B1 and B2 against Escherichia coli isolate showed more potent antimicrobial activity with MIC value of 16 mu g/mL than some of the reference drugs. The compounds' interactions on the DNA gyrase enzyme were evaluated by molecular docking and molecular dynamics simulations. Docked compounds have demonstrated superimposition in the DNA gyrase ATP binding site with similar protein-ligand interactions. With 50 ns duration molecular dynamics simulations, the average RMSD value of the DNA gyrase subunit B protein and B1, B2, B3, and B4 complexes were measured at about 0.15 nm. The ligands-bound DNA gyrase subunit B protein is a little less RMSF value and more stable than the apoprotein form between 45-49 residues in the active site amino acids region. Geometric optimization parameters, HOMO-LUMO orbital energies, and other electronic parameters derived from these energies, MEP, and NBO analysis were performed the DFT/B3LYP theory and 6-311G (d,p) basis set. The Delta E: LUMO-HOMO of the two most active compounds B1 and B2 are 4.2928 and 4.3219, respectively. The compounds' predicted ADME profiles were in line with Lipinski and other limiting rules. (C) 2021 Elsevier B.V. All rights reserved.en_US
dc.identifier.doi10.1016/j.molstruc.2021.130151
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85101839812en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2021.130151
dc.identifier.urihttps://hdl.handle.net/20.500.14551/19036
dc.identifier.volume1234en_US
dc.identifier.wosWOS:000637751000010en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevieren_US
dc.relation.ispartofJournal Of Molecular Structureen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectBenzoxazoleen_US
dc.subjectAntimicrobial Activityen_US
dc.subjectMolecular Dockingen_US
dc.subjectMolecular Dynamicsen_US
dc.subjectDFTen_US
dc.subjectBenzoxazolesen_US
dc.titleSynthesis, Molecular Docking, Molecular Dynamics, DFT and Antimicrobial Activity Studies of 5-substituted-2-(p-methylphenyl)benzoxazole Derivativesen_US
dc.typeArticleen_US

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