Design, synthesis, in-vitro and in-silico studies of chromone-isoxazoline conjugates as anti-bacterial agents

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dc.authoridhadni, hanine/0000-0002-4952-9533
dc.authoridChalkha, Mohammed/0000-0002-9400-2183
dc.authoridEL YAZIDI, Mohamed/0000-0002-2772-6632
dc.authoridNAKKABI, Asmae/0000-0002-9845-243X
dc.authoridTUZUN, BURAK/0000-0002-0420-2043
dc.contributor.authorKanzouai, Youssra
dc.contributor.authorChalkha, Mohammed
dc.contributor.authorHadni, Hanine
dc.contributor.authorLaghmari, Mustapha
dc.contributor.authorBouzammit, Rachid
dc.contributor.authorNakkabi, Asmae
dc.contributor.authorBenali, Taoufiq
dc.date.accessioned2024-10-26T18:09:29Z
dc.date.available2024-10-26T18:09:29Z
dc.date.issued2023
dc.departmentSivas Cumhuriyet Üniversitesi
dc.description.abstractA novel series of chromone-isoxazoline conjugates was successfully synthesized by the O-alkylation and 1,3dipolar cycloaddition reactions using methyl 7-hydroxy-4H-chromone-3-carboxylate as starting material. The structures of the synthesized hybrid compounds were determined using spectroscopic techniques, and mass spectrometry. The in-vitro antibacterial activity of the target compounds was tested against four bacterial strains, and it was found that compound 5e was active against the strains B. subtilis and P. mirabilis. Theoretical calculations were made at the B3LYP, HF, and M062X level on a 6-31++g(d,p) basis in order to optimize the geometric structures and calculate the geometric and electronic structure parameters of the target compounds. In addition, molecular docking studies were performed to understand and identify the mode of interaction between the hybrid compound 5e and the bacterial proteins of B. subtilis and P. mirabilis. The outcomes revealed that the hybrid compound 5e displayed strong binding affinities within the target receptors' active site. Also, a 100 ns molecular dynamics simulation was used to assess the behavior and stability of the complexes formed between ligand 5e and the bacterial receptors. Lastly, in silico ADMET analyses suggest that the target compounds exhibit favorable pharmacokinetic properties, including significant oral bioavailability.
dc.description.sponsorshipScientific Research Project Fund of Sivas Cumhuriyet University (CUBAP) [RGD-020]
dc.description.sponsorshipAcknowledgements The numerical calculations reported in this paper were fully/partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources) . This work was supported by the Scientific Research Project Fund of Sivas Cumhuriyet University (CUBAP) under the project number RGD-020.
dc.identifier.doi10.1016/j.molstruc.2023.136205
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85165673978
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2023.136205
dc.identifier.urihttps://hdl.handle.net/20.500.12418/30139
dc.identifier.volume1293
dc.identifier.wosWOS:001047319500001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectChromone-isoxazoline conjugates
dc.subjectAntibacterial activity
dc.subjectDFT
dc.subjectMolecular docking
dc.subjectMolecular dynamics
dc.titleDesign, synthesis, in-vitro and in-silico studies of chromone-isoxazoline conjugates as anti-bacterial agents
dc.typeArticle

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