Exploring the anticancer potential of new 3-cyanopyridine derivatives bearing N-acylhydrazone motif: Synthesis, DFT calculations, cytotoxic evaluation, molecular modeling, and antioxidant properties

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dc.contributor.authorKadi, Ibtissem
dc.contributor.authorSekerci, Guldeniz
dc.contributor.authorBoulebd, Houssem
dc.contributor.authorZebbiche, Zineddine
dc.contributor.authorTekin, Suat
dc.contributor.authorBenarous, Khedidja
dc.contributor.authorSerseg, Talia
dc.date.accessioned2026-04-04T13:37:39Z
dc.date.available2026-04-04T13:37:39Z
dc.date.issued2024
dc.departmentİnönü Üniversitesi
dc.description.abstract3-Cyanopyridine derivatives are known for exhibiting excellent anticancer activity due to their strong capability to inhibit various biological targets, including Pim-1 kinase, survivin, and tubulin polymerization. On the other hand, N-acylhydrazones (NAH) are known to be a very versatile motif in medicinal chemistry and drug design. Based on these data, we report in this paper, the synthesis of novel 3-cyanopyridines incorporating N-acyl hydrazine scaffold, the evaluation of their cytotoxicity on the breast (MCF-7) and ovarian (A-2780) cancer cell lines and their antioxidant properties. Excluding 4a and 4d, all tested molecules exhibited high cytotoxicity against A-2780, with IC50 values ranging from 1.14 to 1.76 mu M. Conversely, only four molecules 3d, 4b, 4c, and 4d demonstrated cytotoxicity against MCF-7, with IC50 values ranging from 1.14 to 3.38 mu M. On the other hand, all the tested molecules exhibited a moderate antioxidant capacity in both the DPPH and metal chelation assays. Docking and molecular dynamics studies revealed that 2d, 3d, and 4d are potential inhibitors of tubulin and the oe strogen receptor, which may explain their high cytotoxicity. These results are promising to study these newly synthesized 3-cyanopyridine-N-acylhydrazones in depth for use as potential anticancer candidates. A series of novel N-acetylhydrazone motifs-containing 3-cyanopyridine derivatives were synthesized, and their anticancer properties against MCF-7 and A2780 cancer cell lines, along with their antioxidant capacities, were investigated under in vitro conditions. Additionally, density functional theory (DFT) calculations and molecular modeling were conducted in silico. image
dc.description.sponsorshipThe supercomputing resources used in this work to perform DFT calculations were supported by the HPC of UCI-UFMC (Unite de Calcul Intesif of the University Freres Mentouri Constantine 1).
dc.identifier.doi10.1002/jbt.23819
dc.identifier.issn1095-6670
dc.identifier.issn1099-0461
dc.identifier.issue9
dc.identifier.orcid0000-0003-0094-3941
dc.identifier.orcid0000-0001-7784-4138
dc.identifier.orcid0000-0002-7727-8583
dc.identifier.orcid0000-0002-7180-9486
dc.identifier.pmid39180345
dc.identifier.scopus2-s2.0-85202076796
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1002/jbt.23819
dc.identifier.urihttps://hdl.handle.net/11616/109970
dc.identifier.volume38
dc.identifier.wosWOS:001296653200001
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.subject3-cyanopyridine
dc.subjectantioxidant
dc.subjectcytotoxicity
dc.subjectdocking
dc.subjectMCF-7 and A-2780
dc.subjectmolecular dynamics
dc.subjectN-acylhydrazone
dc.titleExploring the anticancer potential of new 3-cyanopyridine derivatives bearing N-acylhydrazone motif: Synthesis, DFT calculations, cytotoxic evaluation, molecular modeling, and antioxidant properties
dc.typeArticle

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