Copper(II) complexes with N,O-donor azo-Schiff base ligands: Synthesis, structure, DFT studies, molecular docking, anticancer and antimicrobial activity

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dc.contributor.authorKahraman, Sevgi
dc.contributor.authorHepokur, Ceylan
dc.contributor.authorErci, Fatih
dc.contributor.authorErkan, Sultan
dc.contributor.authorCetin, Seda
dc.contributor.authorKose, Muhammet
dc.contributor.authorKurtoglu, Mukerrem
dc.date.accessioned2025-05-04T16:47:02Z
dc.date.available2025-05-04T16:47:02Z
dc.date.issued2025
dc.departmentSivas Cumhuriyet Üniversitesi
dc.description.abstractTwo Schiff base ligands containing 4-(fluoro or bromo)phenylazo group 2, 3 and their Cu(II) complexes 4 and 5 were prepared, and their structures were characterized by analytical, spectral and computational methods. The crystal structures of the ligands 2, 3 and their Cu(II) complexes 4 and 5 were determined by single crystal XRD studies. The XRD data revealed that both ligands 2 and 3 are in phenol-imine tautomeric state in the crystalline form. In the structures of Cu(II) complexes 4 and 5, each Cu(II) is four coordinated binding to NO (imine nitrogen and donor set of two azo-Schiff base ligands with approximately square plane geometry. The elemental analysis data reveal that the azo-Schiff base Cu(II) complexes have 1:2 (M: L) stoichiometry. The electronic absorption spectra and quantum chemical calculations suggest a distorted square planer geometry for the complexes. Antibacterial activities of the azo-Schiff bases and their Cu(II) complexes were screened against of Bacillus cereus and Staphylococcus aureus, Escherichia coli and Salmonella typhimurium. The antitumor activity of the has been investigated across different cancer cell lines, including human breast cancer (MCF-7, MDA-MB-231), human colon colorectal adenocarcinoma (HT-29), rat glioma (C6), human Gastric Adenocarcinoma (AGS) and cisplatin was used as the standard drug. The antiproliferative efficacy of compound 5 was assessed through flow cytometry and annexin-V analysis, while the metabolic pathway active in breast cancer cells was scrutinized to understand its mechanism of action. The cytotoxic effects of synthesized ligands and their Cu(II) complexes were evaluated on multiple cancer cell lines, revealing that Cu(II) complex 5 had the highest potency against MDAMB-231 cells with an IC50 value of 4.45 mu g/mL, demonstrating significant selectivity for cancer cells over healthy cells, and indicating its potential as an effective therapeutic agent in cancer treatment, particularly as it induced cell death while minimally affecting healthy cells. Furthermore, in silico studies were conducted to evaluate the antibacterial and anticancer properties of compounds 1-5. The findings revealed that compound 5 exhibited the highest antibacterial activity against S. aureus and B. cereus, as well as significant cytotoxic effects on breast cancer cells. All in all, two Schiff base ligands containing 4-(fluoro or bromo)phenylazo group 2, 3 and their Cu(II) complexes 4, 5 hold promise as prospective candidates for the development of novel anticancer drugs.
dc.description.sponsorshipResearch Found of Kahramanmaras Sutcu Imam University , Kahramanmaras, Turkiye [2023/5-7 M]
dc.description.sponsorshipThe authors thank Research Found of Kahramanmaras Sutcu Imam University for financial support (Project No : 2023/5-7 M) , Kahramanmaras, Turkiye.
dc.identifier.doi10.1016/j.poly.2025.117393
dc.identifier.issn0277-5387
dc.identifier.issn1873-3719
dc.identifier.scopus2-s2.0-85214523279
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1016/j.poly.2025.117393
dc.identifier.urihttps://hdl.handle.net/20.500.12418/35458
dc.identifier.volume269
dc.identifier.wosWOS:001397983300001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherPergamon-Elsevier Science Ltd
dc.relation.ispartofPolyhedron
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250504
dc.subjectAzo-Schiff base
dc.subjectCopper(II) complex
dc.subjectComputational research
dc.subjectBiological activity
dc.subjectMolecular docking
dc.titleCopper(II) complexes with N,O-donor azo-Schiff base ligands: Synthesis, structure, DFT studies, molecular docking, anticancer and antimicrobial activity
dc.typeArticle

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