Spectrophotometric, voltammetric and cytotoxicity studies of 2-hydroxy-5-methoxyacetophenone thiosemicarbazone and its N(4)-substituted derivatives: A combined experimental-computational study

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dc.contributor.authorAkgemci, Emine Guler
dc.contributor.authorSaf, Ahmet Ozgur
dc.contributor.authorTasdemir, Halil Ugur
dc.contributor.authorTurkkan, Ercan
dc.contributor.authorBingol, Haluk
dc.contributor.authorTuran, Suna Ozbas
dc.contributor.authorAkkiprik, Mustafa
dc.date.accessioned2024-02-23T14:13:44Z
dc.date.available2024-02-23T14:13:44Z
dc.date.issued2015
dc.departmentNEÜen_US
dc.description.abstractIn this study, 2-hydroxy-5-methoxyacetophenone thiosemicarbazone (HMAT) and its novel N(4) substituted derivatives were synthesized and characterized by different techniques. The optical band gap of the compounds and the energy of HOMO were experimentally examined by UV-vis spectra and cyclic voltammetry measurements, respectively. Furthermore, the conformational spaces of the compounds were scanned with molecular mechanics method. The geometry optimization, HOMO and LUMO energies, the energy gap of the HOMO LUMO, dipole moment of the compounds were theoretically calculated by the density functional theory B3LY10/6-3114-+G(d,p) level. The minimal electronic excitation energy and maximum wavelength calculations of the compounds were also performed by TD-DFT//B3LYP/6-311++G(d,p) level of theory. Theoretically calculated values were compared with the related experimental values. The combined results exhibit that all compounds have good electron-donor properties which affect anti-proliferative activity. The cytotoxic effects of the compounds were also evaluated against HeLa (cervical carcinoma), MCF-7 (breast carcinoma) and PC-3 (prostatic carcinoma) cell lines using the standard MIT assay. All tested compounds showed antiproliferative effect having IC50 values in different range. In comparison with that of HMAT, it was obtained that while ethyl group on 4(N)-substituted position decreased in potent anti-proliferative effect, the phenyl group on the position increased in anti-proliferative effect for the tested cancer cell line. Considering the molecular energy parameters, the cytotoxicity activities of the compounds were discussed. (C) 2014 Elsevier B.V. All rights reserved.en_US
dc.description.sponsorshipScientific Research Projects of Necmettin Erbakan Universityen_US
dc.description.sponsorshipThe authors are grateful to the Scientific Research Projects of Necmettin Erbakan University for financial support.en_US
dc.identifier.doi10.1016/j.saa.2014.09.087
dc.identifier.endpage725en_US
dc.identifier.issn1386-1425
dc.identifier.pmid25448971en_US
dc.identifier.scopus2-s2.0-84911928940en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage719en_US
dc.identifier.urihttps://doi.org/10.1016/j.saa.2014.09.087
dc.identifier.urihttps://hdl.handle.net/20.500.12452/12548
dc.identifier.volume136en_US
dc.identifier.wosWOS:000347585300067en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.publisherPergamon-Elsevier Science Ltden_US
dc.relation.ispartofSpectrochimica Acta Part A-Molecular And Biomolecular Spectroscopyen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectThiosemicarbazoneen_US
dc.subjectUv-Vis Spectroscopyen_US
dc.subjectCyclic Voltammetryen_US
dc.subjectDft Calculationsen_US
dc.subjectCytotoxicityen_US
dc.titleSpectrophotometric, voltammetric and cytotoxicity studies of 2-hydroxy-5-methoxyacetophenone thiosemicarbazone and its N(4)-substituted derivatives: A combined experimental-computational studyen_US
dc.typeArticleen_US

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