title: 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.
abstract: 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, 11b 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, 11b 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 G/G and A/A nucleotides, respectively.
authors.affiliation: Department of Chemistry, Gaziosmanpaşa University, 60150 Taşlıçiftlik Kampüsü, Tokat, Turkey.
authors.forename: Hüseyin
authors.initials: H
authors.lastname: Akbaş
authors.forename: Aytuğ
authors.initials: A
authors.lastname: Okumuş
authors.forename: Zeynel
authors.initials: Z
authors.lastname: Kılıç
authors.forename: Tuncer
authors.initials: T
authors.lastname: Hökelek
authors.forename: Yasemin
authors.initials: Y
authors.lastname: Süzen
authors.forename: L Yasemin
authors.initials: LY
authors.lastname: Koç
authors.forename: Leyla
authors.initials: L
authors.lastname: Açık
authors.forename: Z Betül
authors.initials: ZB
authors.lastname: Celik
mesh_terms: D000588:Amines / Q000737:chemistry*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D002175:Candida / Q000187:drug effects*; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D004247:DNA / Q000737:chemistry / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D061986:MCF-7 Cells; D053078:Membrane Potential, Mitochondrial / Q000187:drug effects; D008958:Models, Molecular; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010957:Plasmids / Q000187:drug effects; D013141:Spiro Compounds / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000588:Amines; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D009943:Organophosphorus Compounds; D013141:Spiro Compounds; D004247:DNA
keywords: Antimicrobial activity; Crystal structure; Cytotoxic activity; DNA interaction; HeLa cell line; Monofluorobenzylspirocyclotriphosphazenes