Synthesis, characterization, and DFT study of novel metallo phtalocyanines with four carboranyl clusters as photosensitisers for the photodynamic therapy of breast cancer cells

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dc.authoridÖzer Bekaroğlu / 0000-0002-9249-2385en_US
dc.authorwosidÖzer Bekaroğlu / N-9731-2013
dc.contributor.authorSener, Sevil
dc.contributor.authorBayrac, A. Tahir
dc.contributor.authorSener, B. Bilgenur
dc.contributor.authorTozlu, Cem
dc.contributor.authorAcar, Nursel
dc.contributor.authorSalih, Bekir
dc.contributor.authorYuksel, Mithat
dc.contributor.authorBekaroğlu, Özer
dc.date.accessioned2020-08-30T20:06:58Z
dc.date.available2020-08-30T20:06:58Z
dc.date.issued2019
dc.departmentİstinye Üniversitesi, Eczacılık Fakültesi, Eczacılık Temel Bilimleri Bölümüen_US
dc.descriptionBayrac, Abdullah Tahir T/0000-0002-8049-7867; Bekaroglu, Ozer ---/0000-0002-9249-2385; Acar Selcuki, Nursel/0000-0001-9292-0637en_US
dc.description.abstractThe synthesis and characterization of novel Zn(II) and Co(II) phthalocyanines 4 and 5, respectively containing four o-carboranyl units (40 boron atoms, 32.5% boron by weight) at the peripheral positions are described. The phthalocyanines (Pcs) were synthesized by cyclotetramerization of the previously prepared precursor 4-(2-thiol-o-carboranyl)thiolato-phthalonitrile 3 with the presence of metal salt in boiling dry DMF under a dry nitrogen atmosphere. They were characterized by elemental analysis, UV-Vis, FT-IR, MALDI-TOF mass and H-1 NMR spectrometry. To elucidate the structural, spectroscopic and bonding properties of the obtained compounds, calculations with DFT/TD-DFT(Density Functional Theory/Time Dependent-Density Functional Theory) were performed. The cytotoxic effects of 4 and 5 on cancer cells and epithelial cells were determined. The targeted cytotoxicities of both compounds against cancer cells were analyzed with the cell viability test. Although, 4 caused less PDT (Photodynamic therapy) based decrease in cell viability of cancer cell line in comparison to 5, it showed comparatively high cytotoxicity against cancer cells but not epithelial cells. The IC50 (half maximal inhibitory concentration) values indicate that 4 with PDT shows 17.3 fold more cytotoxicity to breast cancer cells than epithelial cells. The selectivity in cytotoxicity of 4 makes it a good candidate for cancer treatment. Interestingly, 5 was found to be highly cytotoxic for both cancer and epithelial cell lines. Considerably, 5 might be used as a cancer drug when combined with targeting agents such as antibodies and aptamers.en_US
dc.description.sponsorshipTurkish Academy of Sciences (TUBA)Turkish Academy of Sciencesen_US
dc.description.sponsorshipWe gratefully acknowledge the financial support from Serife Sener Ocal. We also thank computer time on FenCluster provided by Ege University Faculty of Science and TUBITAK-ULAKBIM Truba Resources. Prof. Dr. Bekir Salih gratefully acknowledges the Turkish Academy of Sciences (TUBA) for the partial financial support. We gratefully acknowledge Prof. Dr. Abdurrahman Şengül, for his support during the study.en_US
dc.identifier.citationSener, S., Bayrac, A. T., Sener, B. B., Tozlu, C., Acar, N., Salih, B., … Bekaroglu, O. (2019). Synthesis, characterization, and DFT study of novel metallo phtalocyanines with four carboranyl clusters as photosensitisers for the photodynamic therapy of breast cancer cells. EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 129, 124–131. https://doi.org/10.1016/j.ejps.2018.12.017en_US
dc.identifier.doi10.1016/j.ejps.2018.12.017en_US
dc.identifier.endpage131en_US
dc.identifier.issn0928-0987en_US
dc.identifier.issn1879-0720en_US
dc.identifier.pmid30615930en_US
dc.identifier.scopus2-s2.0-85059646306en_US
dc.identifier.scopusqualityQ1en_US
dc.identifier.startpage124en_US
dc.identifier.urihttps://doi.org/10.1016/j.ejps.2018.12.017
dc.identifier.urihttps://hdl.handle.net/20.500.12713/666
dc.identifier.volume129en_US
dc.identifier.wosWOS:000456591300012en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.institutionauthorBekaroğlu, Özeren_US
dc.language.isoenen_US
dc.publisherElsevieren_US
dc.relation.ispartofEuropean Journal of Pharmaceutical Sciencesen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectMetallophthalocyanineen_US
dc.subjectO-Carboraneen_US
dc.subjectPhotodynamic Therapyen_US
dc.subjectCytotoxen_US
dc.subjectDensity Functional Theoryen_US
dc.titleSynthesis, characterization, and DFT study of novel metallo phtalocyanines with four carboranyl clusters as photosensitisers for the photodynamic therapy of breast cancer cellsen_US
dc.typeArticleen_US

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