title: Spectrophotometric, voltammetric and cytotoxicity studies of 2-hydroxy-5-methoxyacetophenone thiosemicarbazone and its N(4)-substituted derivatives: a combined experimental-computational study.
abstract: In 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 B3LYP/6-311++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 MTT 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.
authors.affiliation: Department of Chemistry Education, Faculty of A.K. Education, University of Necmettin Erbakan, Konya, Turkey. Electronic address: egakgemci@gmail.com.
authors.forename: Emine Guler
authors.initials: EG
authors.lastname: Akgemci
authors.affiliation: Department of Chemistry Education, Faculty of A.K. Education, University of Necmettin Erbakan, Konya, Turkey. Electronic address: aosaf42@gmail.com.
authors.forename: Ahmet Ozgur
authors.initials: AO
authors.lastname: Saf
authors.affiliation: Department of Physic Education, Faculty of A.K. Education, University of Necmettin Erbakan, Konya, Turkey. Electronic address: hutasdemir@konya.edu.tr.
authors.forename: Halil Ugur
authors.initials: HU
authors.lastname: Tasdemir
authors.affiliation: Department of Physic Education, Faculty of A.K. Education, University of Necmettin Erbakan, Konya, Turkey. Electronic address: eturkkan@konya.edu.tr.
authors.forename: Ercan
authors.initials: E
authors.lastname: Türkkan
authors.affiliation: Department of Chemistry Education, Faculty of A.K. Education, University of Necmettin Erbakan, Konya, Turkey. Electronic address: halukbingol@gmail.com.
authors.forename: Haluk
authors.initials: H
authors.lastname: Bingol
authors.affiliation: Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, University of Marmara, Istanbul, Turkey. Electronic address: suna.turan@marmara.edu.tr.
authors.forename: Suna Ozbas
authors.initials: SO
authors.lastname: Turan
authors.affiliation: Department of Medical Biology, School of Medicine, Marmara University, Istanbul, Turkey. Electronic address: makkiprik@marmara.edu.tr.
authors.forename: Mustafa
authors.initials: M
authors.lastname: Akkiprik
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D055664:Electrochemical Techniques; D004583:Electrons; D006801:Humans; D008958:Models, Molecular; D009369:Neoplasms / Q000188:drug therapy; D013056:Spectrophotometry, Ultraviolet; D013882:Thiosemicarbazones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D013882:Thiosemicarbazones
keywords: Cyclic voltammetry; Cytotoxicity; DFT calculations; Thiosemicarbazone; UV–vis spectroscopy