Crystal Structure-Activity Relationship of Some MeO Phenylacrylonitriles: Dual Antimicrobial-Cytotoxic Effects and in Silico Perspectives

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dc.contributor.authorOzen, Leyla Babali
dc.contributor.authorEkici, Oner
dc.contributor.authorOzen, Furkan
dc.contributor.authorBerberler, Suleyman
dc.contributor.authorOzkan, Gul
dc.contributor.authorOzturk, Betul Yilmaz
dc.contributor.authorOztopcu-Vatan, Pinar
dc.date.accessioned2026-04-25T14:19:44Z
dc.date.available2026-04-25T14:19:44Z
dc.date.issued2025
dc.departmentSinop Üniversitesi
dc.description.abstractHerein, methoxy-substituted phenylacrylonitrile derivatives 2(a-c) are synthesized via Knoevenagel condensation and characterized using fourier-transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, and X-ray crystallography (for 2a and 2b). Although compounds 2a and 2b have previously been reported in terms of their structural features, their dual antimicrobial and anticancer activities, as well as crystallographic structure-activity relationships, have not yet been investigated. Notably, no earlier studies assessed their selective cytotoxicity using both cancerous (MCF-7) and healthy (L929) cell lines-a gap addressed in this work. Molecular docking analyzes reveal strong binding affinities to biological targets, including penicillin binding protein 2 (PBP2) (-8.4 kcal mol-1 for 2c) and CDK1/Cks2 (-9.5 kcal mol-1 for 2c), highlighting their dual-action potential. Antimicrobial assays against nine bacterial strains show minimum inhibitory concentration values ranging from 2.5 to 25 mg mL-1, with 2c exhibiting notable activity against gram-positive bacteria. Cytotoxicity assays demonstrate potent effects against MCF-7 cells (IC50: 34 mu M for 2b, 44 mu M for 2a), while 2c shows broader but moderate activity. The integration of crystallographic, docking, and biological assays underscores the therapeutic potential of these derivatives, with 2(a,b) emerging as selective candidates for breast cancer treatment.
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [KBAG-119Z608]; Akdeniz University Scientific Research Projects Unit (AU-BAP) [FBA-2020-5403, FDK-2022-6056]
dc.description.sponsorshipMany thanks to The Scientific and Technological Research Council of Turkey (TUBITAK, KBAG-119Z608) and Akdeniz University Scientific Research Projects Unit (AU-BAP, FBA-2020-5403 and FDK-2022-6056) for financial support. The authors acknowledge the Dokuz Eylul University (Dr. Muhittin Ayguen) for the use of the Gaussian Software Programme.
dc.identifier.doi10.1002/open.202500280
dc.identifier.issn2191-1363
dc.identifier.orcid0000-0001-5800-5021
dc.identifier.orcid0000-0001-9023-6604
dc.identifier.pmid40509614
dc.identifier.scopus2-s2.0-105007887027
dc.identifier.scopusqualityN/A
dc.identifier.urihttps://doi.org/10.1002/open.202500280
dc.identifier.urihttps://hdl.handle.net/11486/8138
dc.identifier.wosWOS:001507648000001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherWiley-V C H Verlag Gmbh
dc.relation.ispartofChemistryopen
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_WOS_20260420
dc.subjectantimicrobial
dc.subjectcrystal structure-activity
dc.subjectcytotoxic
dc.subjectmolecular docking
dc.subjectphenylacrylonitrile
dc.titleCrystal Structure-Activity Relationship of Some MeO Phenylacrylonitriles: Dual Antimicrobial-Cytotoxic Effects and in Silico Perspectives
dc.typeArticle

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