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  • Küçük Resim
    Öğe
    Synthesis, characterization, and DFT study of novel metallo phtalocyanines with four carboranyl clusters as photosensitisers for the photodynamic therapy of breast cancer cells
    (Elsevier, 2019) Sener, Sevil; Bayrac, A. Tahir; Sener, B. Bilgenur; Tozlu, Cem; Acar, Nursel; Salih, Bekir; Yuksel, Mithat; Bekaroğlu, Özer
    The 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.
  • Küçük Resim
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    Synthesis, conductivity, and ımpedance studies on metallophthalocyanines formed across adjacent rings
    (Wiley-V C H Verlag Gmbh, 2019) Sener, Sevil; Selcuki, Nursel Acar; Dumludag, Fatih; Salih, Bekir; Bekaroğlu, Özer
    The synthesis and characterization of Co-II, Zn-II, and Ni-II phthalocyanines (Pcs) 4, 5, and 6, respectively, containing two bis[2-(4-hydroxyphenyl)-2-propyl]benzene groups formed across adjacent rings at the peripheral positions are described. The Pcs were synthesized by cyclotetramerization of the previously prepared precursor 4,4 '-bis[1,3-propylbenzene-2-p-phenoxy]phthalonitrile (3) in the presence of metal salt in boiling dry DMF under a dry nitrogen atmosphere. Elemental analysis, UV-Vis, FT-IR, and H-1-NMR spectroscopy, as well as MALDI-TOF mass spectrometry techniques were used for the characterization of 4. Conductivity (dc and ac) and impedance spectroscopy (IS) measurements were performed on the films of 5 and 6 between the temperatures 293 and 523 K and frequencies 40 and100 kHz. The dc conductivity values were calculated as 2.11 x 10-(10), 3.48 x 10-(10), and 1.90 x 10-(10) S/cm for the films of 4, 5, and 6, respectively, at room temperature. Activation energy values of the films were also calculated. Conductivity (ac) results suggest that the dominant charge transport mechanisms can be explained by the hopping model depending on temperature and frequency range. From impedance spectra and Cole-Cole plots, the relaxation time in the Debye dispersion relation is considered as a distribution of relaxation time values rather than as a single relaxation time. To elucidate the structural, spectroscopic, and bonding properties of the obtained compounds, DFT/TD-DFT calculations were performed.