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    Phosphorus nitrogen compounds: Part 34. Syntheses, structural investigations, cytotoxic and biological activities of spiro-ansa-spiro and spiro-bino-spiro tetrameric phosphazene derivatives
    (Elsevier Science Sa, 2016) Berberoglu, Ipek; Asmafiliz, Nuran; Kilic, Zeynel; Hokelek, Tuncer; Koc, L. Yasemin; Acik, Leyla; Dal, Hakan
    The reactions of N4P4Cl8 with the symmetric N2N2 (1-3) and N2O2 (4) bulky ligands gave partly substituted 2,4-sas (5 and 6), 2,6-sas (7-10) and sbs (11-14) tetrameric phosphazene derivatives. The 2,4-sas-5, 2,6-sas-8 and sbs-12 reacted with pyrrolidine to give fully-substituted tetra-(15 and 16) and dode-capyrrolidinocyclotetraphosphazenes (17-19). The structures of all the phosphazenes were verified by FTIR, MS, H-1, C-13{H-1} and P-31{H-1} NMR, and HSQC spectral data. The crystal structures of 7, 9 and 10 were examined by single crystal X-ray diffraction techniques. The compounds 1-3, 5, 8, 9, 12, 13, 16 and 18 were screened for antimicrobial activity against G(+) and G(-) bacteria and fungi. The compound 16 is found to possess excellent activity (MIC values of 39 and 78 mu M) against fungal pathogen Candida krusei and Candida albicans. Meanwhile, interactions between pBR322 plasmid DNA and 1-3, 5, 8, 9, 12, 13, 14, 16 and 18 were investigated by agarose gel electrophoresis. The compounds 5, 8, 9, 12, 13, 16 and 18 were appraised for their cytotoxic activity against L929 Fibroblast and MDA-MB-231 breast cancer cell lines. Compounds 13 and 16 are as effective as cis-platin. (C) 2016 Elsevier B.V. All rights reserved.
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    Phosphorus-nitrogen compounds: Part 46. The reactions of N3P3Cl6 with bidentate and monodentate ligands: The syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of (N/N)spirocyclotriphosphazenes with 4-chlorobenzyl pendant arm
    (Elsevier Science Sa, 2019) Asmafiliz, Nuran; Berberoglu, Ipek; Ozgur, Mehtap; Kilic, Zeynel; Kayalak, Hande; Acik, Leyla; Hokelek, Tuncer
    In the present study, the partly and fully-substituted monospiro (4-6, 4a-6d), cis-dispiro (7-9), trans-dispiro (10-15) cyclotriphosphazenes were synthesized for the investigations of their chemical, stereogenic and biological properties. The cis/trans phosphazenes (7-12) have two stereogenic P centers. They are expected to be in meso and racemic forms. In addition, the structures of four compounds were evaluated using X-ray crystal-lographic data. Compound 13 was found to be a single enantiomer (RR) in the solid state, as also proved with its CD spectrum. The antibacterial and antifungal activities of the phosphazenes were elucidated for against Gram-positive (G+) and Gram-negative (G-) bacteria, and yeast strains, respectively. Of the compounds, 14 exhibits strong antimicrobial activity against most of the tested organisms, especially B. cereus and E. hirae. MBC and MFC values of compounds on different bacterial and fungal species ranged from < 9.8 mu M to 2500 mu M. Furthermore, the cytotoxic activities of 6, 4c, 10 and 14 were investigated against L929 fibroblast and DLD-1 cells, and 14 was the most cytotoxic compound against DLD-1.