Synthesis and Biological Assessment of Cyanopyridine-Based 1,3,4-Oxadiazole Derivatives: Anticancer Potential, Antioxidant Activity, Molecular Docking, and DFT Calculations

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dc.contributor.authorZebbiche, Zineddine
dc.contributor.authorSekerci, Gueldeniz
dc.contributor.authorHoussem, Boulebd
dc.contributor.authorKucukbay, Fatumetuzzehra
dc.contributor.authorTekin, Suat
dc.contributor.authorKucukbay, Hasan
dc.contributor.authorBoumoud, Boudjemaa
dc.date.accessioned2026-04-04T13:37:38Z
dc.date.available2026-04-04T13:37:38Z
dc.date.issued2025
dc.departmentİnönü Üniversitesi
dc.description.abstractA series of six novel cyanopyridine derivatives bearing a 1,3,4-oxadiazole ring have been synthesized and characterized by FTIR, 13C NMR, 1H NMR, and elemental analysis. DFT calculations were carried out to determine their molecular geometries, electronic properties, and chemical reactivity. Their cytotoxicity has been evaluated against MCF-7 and CaCo-2 human cancer cell lines using the MTT assay. Most compounds displayed poor cytotoxic activity against the MCF-7 cell line except for compound 4e, which showed potent activity with IC50 = 8.352 mu M. However, the CaCo-2 cell line was highly sensitive toward most tested compounds with an IC50 range from 2.612 mu M to 8.394 mu M except for compound 4 d. Molecular docking studies targeting human topoisomerase-II beta revealed that all compounds exhibited excellent binding affinity within the enzyme's active site, with binding energies ranging from -7.33 to -8.28 kcal/mol. These findings suggest a potential anticancer mechanism underlying the observed cytotoxic activities. All tested compounds revealed low antioxidant activity in the DPPH assay. However, compounds 5b and 5 d presented moderate metal chelating activity. These findings underscore the potential anticancer properties of the synthesized cyanopyridine derivatives.
dc.description.sponsorshipMESRS (Ministre de l'Enseignement Suprieur et de la Recherche Scientifique, Algeria); DGRSDT (Direction Generale de la Recherche Scientifique et du Developpement Technologique, Algeria); Inoenue University, Malatya, Turkey
dc.description.sponsorshipWe would like to thank MESRS (Ministere de l'Enseignement Superieur et de la Recherche Scientifique, Algeria) and DGRSDT (Direction Generale de la Recherche Scientifique et du Developpement Technologique, Algeria), for financial support, as well as the HPC resources of UCI-UFMC (Unite de Calcul Intesif of the university Freres Mentouri Constantine 1) for the computational resource used. The authors are grateful also for the financial support from center dotInoenue University, Malatya, Turkey.
dc.identifier.doi10.1002/jbt.70346
dc.identifier.issn1095-6670
dc.identifier.issn1099-0461
dc.identifier.issue6
dc.identifier.orcid0000-0002-7180-9486
dc.identifier.orcid0000-0001-7784-4138
dc.identifier.orcid0000-0002-0811-4454
dc.identifier.orcid0000-0002-7727-8583
dc.identifier.orcid0000-0003-0094-3941
dc.identifier.pmid40528497
dc.identifier.scopus2-s2.0-105008523475
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1002/jbt.70346
dc.identifier.urihttps://hdl.handle.net/11616/109962
dc.identifier.volume39
dc.identifier.wosWOS:001510496800001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherWiley
dc.relation.ispartofJournal of Biochemical and Molecular Toxicology
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_WOS_20250329
dc.subject1,3,4-oxadiazole
dc.subjectantioxidant activity
dc.subjectCaCo-2
dc.subjectcyanopyridine
dc.subjectDFT calculations
dc.subjectMCF-7
dc.subjectmolecular docking
dc.titleSynthesis and Biological Assessment of Cyanopyridine-Based 1,3,4-Oxadiazole Derivatives: Anticancer Potential, Antioxidant Activity, Molecular Docking, and DFT Calculations
dc.typeArticle

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