title: Phosphorus-nitrogen compounds: part 30. Syntheses and structural investigations, antimicrobial and cytotoxic activities and DNA interactions of vanillinato-substituted NN or NO spirocyclic monoferrocenyl cyclotriphosphazenes.
abstract: The gradual Cl replacement reactions of NN (1-3) or NO spirocyclic monoferrocenyl cyclotriphosphazenes (4 and 5) with the potassium salt of 4-hydroxy-3-methoxybenzaldehyde (potassium vanillinate) resulted in the mono (1a-5a), geminal (gem-1b-5b), non-geminal (cis-5b and trans -1b-4b), tri (1c, 3c-5c) and tetra-vanillinato-substituted phosphazenes (1d-5d). All the phosphazene derivatives have stereogenic P-center(s), except tetra-substituted ones. The vanillinatophosphazenes have reversible voltammograms with one-electron anodic and cathodic peaks which are attributed to ferrocenyl redox probe. The structures of the new phosphazene compounds were determined by FTIR, MS, (1)H, (13)C{(1)H} and (31)P{(1)H} NMR spectral data. The solid-state structure of cis -5b was examined by single-crystal X-ray diffraction techniques. In addition, the compounds were tested in HeLa cancer cell lines using MTT assay. The 12 phosphazene derivatives were screened for antimicrobial activity, and 3c was very effective against S. aureus even at 4.88 µM concentration, taking into account the MIC values. Besides, interactions between the phosphazenes and pBR322 plasmid DNA were also investigated.
authors.affiliation: Department of Chemistry, Karabük University, 78050, Karabük, Turkey.
authors.forename: Yasemin
authors.initials: Y
authors.lastname: Tümer
authors.affiliation: Department of Biology, Ankara University, 06100, Ankara, Turkey.
authors.forename: L Yasemin
authors.initials: LY
authors.lastname: Koç
authors.affiliation: Department of Chemistry, Ankara University, 06100, Ankara, Turkey.
authors.forename: Nuran
authors.initials: N
authors.lastname: Asmafiliz
authors.affiliation: Department of Chemistry, Ankara University, 06100, Ankara, Turkey. zkilic@science.ankara.edu.tr.
authors.forename: Zeynel
authors.initials: Z
authors.lastname: Kılıç
authors.affiliation: Department of Physics, Hacettepe University, 06800, Ankara, Turkey.
authors.forename: Tuncer
authors.initials: T
authors.lastname: Hökelek
authors.affiliation: Department of Biology, Gazi University, 06500, Ankara, Turkey.
authors.forename: Hossien
authors.initials: H
authors.lastname: Soltanzade
authors.affiliation: Department of Biology, Gazi University, 06500, Ankara, Turkey.
authors.forename: Leyla
authors.initials: L
authors.lastname: Açık
authors.affiliation: Department of Metallurgical and Materials Engineering, Sinop University, 57000, Sinop, Turkey.|Department of Analytical Chemistry, Hacettepe University, 06100, Ankara, Turkey.
authors.forename: Mehmet Lütfi
authors.initials: ML
authors.lastname: Yola
authors.affiliation: Department of Chemical Engineering, Kyrgyzstan-Turkey Manas University, Bishkek, Kyrgyzstan.
authors.forename: Ali Osman
authors.initials: AO
authors.lastname: Solak
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D001547:Benzaldehydes / Q000737:chemistry / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D018360:Crystallography, X-Ray; D004247:DNA / Q000737:chemistry; D004354:Drug Screening Assays, Antitumor; D005296:Ferrous Compounds / Q000737:chemistry / Q000494:pharmacology*; D006367:HeLa Cells; D006801:Humans; D008826:Microbial Sensitivity Tests; D050296:Microbial Viability / Q000187:drug effects; D008968:Molecular Conformation; D009943:Organophosphorus Compounds / Q000737:chemistry / Q000494:pharmacology*; D010957:Plasmids / Q000737:chemistry; D013211:Staphylococcus aureus / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D001547:Benzaldehydes; D005296:Ferrous Compounds; D009943:Organophosphorus Compounds; D004247:DNA