Synthesis of anti-4-phenoxyphenylaminoglyoxime and its some transition metal complexes: Spectral, DFT, electrochemical and anticancer activity studies

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dc.contributor.authorFindik, Mukerrem
dc.contributor.authorUcar, Asuman
dc.contributor.authorTurkkan, Ercan
dc.contributor.authorPehlivanoglu, Suray
dc.contributor.authorOzcan, Emine
dc.date.accessioned2024-02-23T14:13:17Z
dc.date.available2024-02-23T14:13:17Z
dc.date.issued2020
dc.departmentNEÜen_US
dc.description.abstractanti-4-phenoxyphenylaminoglyoxime (LH2) was synthesized starting from 4-aminodiphenylether and anti-chloroglyoxime in absolute ethanol. Then, mononuclear complexes [Ni(II) and Cu(II)] of LH2 were synthesized with the metal:ligand ratio of 1:2. The LH2 and its complexes [Ni(LH)(2) and Cu(LH)(2)] were characterized by elemental analysis, FT-IR, Raman, UV-vis, thermogravimetric analysis (TGA), H-1 NMR, C-13 NMR, heteronuclear multiple bond correlation (HMBC) spectroscopy and theoretical DFT studies. Also, redox properties of the ligand and its complexes were investigated by cyclic voltammetry in DMSO solution at room temperature. Conformational space was scanned with molecular mechanic simulations and then the possible stable conformers of LH2 ligand were determined by B3LYP/6-311++G (d,p) level calculations. The Ni(LH)(2) and Cu(LH)(2) metal complexes were modeled theoretically using B3LYP/LanL2DZ level. The theoretical vibrational frequencies were calculated by using optimization calculation levels. The NMR parameters of LH2 ligand, Cu(LH)(2) and Ni(LH)(2) metal complexes were calculated at mPW1PW91/6-311 + G (2d,p) level. Theoretically calculated values were compared with the related experimental values. The DFT calculation results have been used to predict and interpret the molecular structures of LH2 ligand and its complexes. The geometry around nickel in Ni(LH)(2) and around cupper in Cu(LH)(2) complex are almost square planar. In addition, we evaluated the efficacy of LH2 ligand and its Ni(LH)(2) and Cu(LH)(2) complexes in the breast adenocarcinoma cell line (MCF7). Our data showed that the metal compounds affect positively the cytotoxic activity of the ligand (LH2). The metal complexes, especially Ni(LH)(2) complex, exhibited noteworthy biological activity against the viability of MCF7 cells. (C) 2020 Elsevier B.V. All rights reserved.en_US
dc.description.sponsorshipResearch Fund of Selcuk University [09201024]en_US
dc.description.sponsorshipThis work was supported by the Research Fund of Selcuk University Project Number: 09201024. The authors thank Dr Umit Ceylan (Department of Medical Services and Techniques, Vocational High School of Health Services, Giresun University, 28100 Giresun, Turkey) for providing help for the preliminary theoretical vibrational frequencies calculations and assignments by Gauss View 5.0.en_US
dc.identifier.doi10.1016/j.molstruc.2020.128190
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85083356856en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2020.128190
dc.identifier.urihttps://hdl.handle.net/20.500.12452/12369
dc.identifier.volume1215en_US
dc.identifier.wosWOS:000537220200020en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevieren_US
dc.relation.ispartofJournal Of Molecular Structureen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectVic-Dioximeen_US
dc.subjectTransition Metal Complexesen_US
dc.subjectDften_US
dc.subjectAnticancer Activityen_US
dc.titleSynthesis of anti-4-phenoxyphenylaminoglyoxime and its some transition metal complexes: Spectral, DFT, electrochemical and anticancer activity studiesen_US
dc.typeArticleen_US

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