Bisbenzoxazole Derivatives: Design, Synthesis, in Vitro Antimicrobial, Antiproliferative Activity, and Molecular Docking Studies

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dc.authoridHAJ ERSAN, RONAK/0000-0001-6651-5910
dc.authoridDuran, Nizami/0000-0002-2766-3491
dc.authoridDogen, Aylin/0000-0002-0388-306X
dc.contributor.authorErsan, Ronak Haj
dc.contributor.authorAlagoz, Mehmet Abdullah
dc.contributor.authorDogen, Aylin
dc.contributor.authorDuran, Nizami
dc.contributor.authorBurmaoglu, Serdar
dc.contributor.authorAlgul, Oztekin
dc.date.accessioned2024-09-18T20:04:32Z
dc.date.available2024-09-18T20:04:32Z
dc.date.issued2022
dc.departmentHatay Mustafa Kemal Üniversitesien_US
dc.description.abstractFour series of bisbenzoxazole derivatives were designed, synthesized, and screened for antiproliferative and antimicrobial activities. Generally, all synthesized bisbenzoxazoles (9-24) displayed significant antiproliferative activity; these effects were shown to be related to oxazole rings and substituents in bisbenzoxazole compounds. Especially, the series bearing chloro-substituent (9-12) exhibited better antiproliferative activity with higher selectivity than the other series (13-24); the IC50 values were observed in the range of 0.045-0.342 mu M. Interestingly, only the compound with a nitro substituent (22) showed maximum potency with an IC50 value of 0.011 mu M, which is two-fold more active than the standard drug methotrexate, with moderate selectivity. The compounds bearing fluoro-substituent (14-16) were found to exhibit potent antibacterial activity against the Gram-positive Enterococcus faecalis, with a MIC value of 62.5 mu g/mL, and moderate activity against Gram-negative bacteria and fungi. Only the compound 23 showed potent activity against Escherichia coli, with a MIC value of 62.5 mu g/mL. In order to better evaluate the activity results, crystal structures of five different proteins Human Anaplastic Lymphoma Kinase (PDB ID: 2XP2), CYP2C8dH complexed (PDB ID: 2NNI), factor-human kinase-beta enzyme IKK-beta enzyme (PDB ID: 4KIK), a tubulin heterodimer complex containing alpha and beta sub-units (PDB ID: 1Z2B) and penicillin-binding protein 4 (PBP4) from Enterococcus faecalis (PDB ID: 6MKI) were used in the docking study to examine antiproliferative and antimicrobial activity. Finally, an ADMET screening test was applied to determine the drug-like, toxicological, and optimum physicochemical properties for all of the synthesized compounds. The strategy applied in this research may act as a perspective for the rational design of potential anticancer drugs.en_US
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [115S190]; Mersin University [BAP-SBE-2018-1-TP3-2911]en_US
dc.description.sponsorshipWe thank the Scientific and Technological Research Council of Turkey (TUBITAK Grant Number: 115S190) and Mersin University for their financial support (BAP-SBE-2018-1-TP3-2911).en_US
dc.identifier.doi10.1080/10406638.2020.1852589
dc.identifier.endpage3123en_US
dc.identifier.issn1040-6638
dc.identifier.issn1563-5333
dc.identifier.issue6en_US
dc.identifier.scopus2-s2.0-85096821382en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage3103en_US
dc.identifier.urihttps://doi.org/10.1080/10406638.2020.1852589
dc.identifier.urihttps://hdl.handle.net/20.500.12483/8229
dc.identifier.volume42en_US
dc.identifier.wosWOS:000594055500001en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherTaylor & Francis Ltden_US
dc.relation.ispartofPolycyclic Aromatic Compoundsen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectBisbenzoxazoleen_US
dc.subjectsynthesisen_US
dc.subjectantimicrobial activityen_US
dc.subjectantiproliferative activityen_US
dc.subjectmolecular dockingen_US
dc.titleBisbenzoxazole Derivatives: Design, Synthesis, in Vitro Antimicrobial, Antiproliferative Activity, and Molecular Docking Studiesen_US
dc.typeArticleen_US

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