Phosphorus-nitrogen compounds part 27. Syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing secondary amino and pendant (4-fluorobenzyl)spiro groups

AKBAŞ H., OKUMUŞ A., Kilic Z., Hokelek T., SÜZEN DEMİRCİOĞLU Y., Koc L. Y., ...More

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol.70, pp.294-307, 2013 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 70
  • Publication Date: 2013
  • Doi Number: 10.1016/j.ejmech.2013.09.046
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Page Numbers: pp.294-307
  • Keywords: Monofluorobenzyl-spirocyclotriphosphazenes, Crystal structure, Antimicrobial activity, Cytotoxic activity, DNA interaction, HeLa cell line, BIOLOGICAL-ACTIVITIES, ANTICANCER AGENTS, CYCLOPHOSPHAZENES, DERIVATIVES, APOPTOSIS, SPECTRA, BINDING
  • Anadolu University Affiliated: No


A number of partly (7-9) and fully (10a-12d. Scheme 1) substituted mono(4-fluorobenzyl)spiro cyclotriphosphazenes was prepared. The structures of the compounds were determined by MS, FTIR, 1D and 2D NMR techniques. The crystal structures of 9, llb and 12b were verified by X-ray diffraction analysis. In vitro cytotoxic activity of the phosphazenes (10a-12d) against HeLa cervical cancer cell lines was evaluated. Compound 12c was found to be the most effective, as it is a cytotoxic reagent that might activate apoptosis by altering mitochondrial membrane potential. Compounds 10b, lib and 12b showed very good activity against yeast strains Candida tropicalis and Candida albicans. BamHI and HindIII digestion results demonstrate that the compounds (10a-12a, 10b-12b, 10d-12d), and (9,10c-12c) bind with GIG and A/A nucleotides, respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.