title: Phosphorus-nitrogen compounds. Part 29. Syntheses, crystal structures, spectroscopic and stereogenic properties, electrochemical investigations, antituberculosis, antimicrobial and cytotoxic activities and DNA interactions of ansa-spiro-ansa cyclotetraphosphazenes.
abstract: A number of novel ansa-spiro-ansa (asa) cyclotetraphosphazenes (1a-5b) was prepared in the range of 63-90 % yields. The structures of the compounds were verified by MS, FTIR, (1)H, (13)C{(1)H} and (31)P{(1)H} NMR, heteronuclear single quantum coherence (HSQC), and heteronuclear multiple-bond correlation (HMBC) techniques. The crystal structures of 1b, 2c and 5a were determined by X-ray crystallography. The compound 2c was analyzed by the changes in the (31)P{(1)H}NMR spectrum in addition of the chiral solvating agent; (R)-(+)-2,2,2-trifluoro-1-(9'-anthryl)-ethanol (CSA), to investigate its stereogenic properties. The result supports that compound 2c was found to be in the racemic mixture. Cyclic voltammetric and chronoamperometric data of the mono-ferrocenyl-spiro-asa-cyclotetraphosphazenes exhibited electrochemically reversible one-electron oxidation of Fe redox centres. The mono-ferrocenyl-spiro-asa compounds (3a-5b) were evaluated for antituberculosis activity against reference strain Mycobacterium tuberculosis H37Rv and M. tuberculosis clinical strain, which is resistant to rifampicin and isoniazid. These compounds appear not to be good candidates for being antituberculosis agents to clinical strains. All of the compounds were screened for antibacterial activities against G(+) and G(-) bacteria, and for antifungal activities against yeast strains. They seem to be more active against Gram positive bacteria than Gram negative. The interactions of the phosphazenes with plasmid DNA and the evaluations for cytotoxic activity against MCF-7 breast cancer cell lines were investigated. The compounds 1b, 2b, 3a and 4a were found to be more effective than Cisplatin against MCF-7 breast cancer cell lines at lower concentrations.
authors.affiliation: Department of Chemistry, Ankara University, 06100 Ankara, Turkey.
authors.forename: Gamze
authors.initials: G
authors.lastname: Elmas
authors.affiliation: Department of Chemistry, Ankara University, 06100 Ankara, Turkey.
authors.forename: Aytuğ
authors.initials: A
authors.lastname: Okumuş
authors.affiliation: Department of Biology, Ankara University, 06100 Ankara, Turkey.
authors.forename: L Yasemin
authors.initials: LY
authors.lastname: Koç
authors.affiliation: Department of Biology, Gazi University, 06500 Ankara, Turkey.
authors.forename: Hossien
authors.initials: H
authors.lastname: Soltanzade
authors.affiliation: Department of Chemistry, Ankara University, 06100 Ankara, Turkey. Electronic address: 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 Chemistry, Anadolu University, 26470 Eskişehir, Turkey.
authors.forename: Hakan
authors.initials: H
authors.lastname: Dal
authors.affiliation: Department of Biology, Gazi University, 06500 Ankara, Turkey.
authors.forename: Leyla
authors.initials: L
authors.lastname: Açık
authors.affiliation: Department of Chemistry, Dumlupınar University, 43270 Kütahya, Turkey.
authors.forename: Zafer
authors.initials: Z
authors.lastname: Üstündağ
authors.affiliation: Department of Clinical Microbiology, Kocaeli University, 41380 Kocaeli, Turkey.
authors.forename: Devrim
authors.initials: D
authors.lastname: Dündar
authors.affiliation: Department of Clinical Microbiology, Kocaeli University, 41380 Kocaeli, Turkey.
authors.forename: Makbule
authors.initials: M
authors.lastname: Yavuz
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004247:DNA / Q000187:drug effects*; D006801:Humans; D061986:MCF-7 Cells; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D017672:Nitrogen Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D017553:Phosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D000995:Antitubercular Agents; D017672:Nitrogen Compounds; D017553:Phosphorus Compounds; D004247:DNA
keywords: Antituberculosis activity; Asa-cyclotetraphosphazenes; Biological activity; Chirality; Crystal structure; Cytotoxic activity