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
| Autor: | Aytuğ Okumuş, Devrim Dündar, Tuncer Hökelek, Gamze Elmas, Leyla Açık, Hossien Soltanzade, Makbule Yavuz, Hakan Dal, Zafer Üstündağ, L. Yasemin Koç, Zeynel Kılıç |
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| Přispěvatelé: | Anadolu Üniversitesi, Fen Fakültesi, Fizik Bölümü |
| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
Models
Molecular Magnetic Resonance Spectroscopy Stereochemistry Gram-positive bacteria Antitubercular Agents Antineoplastic Agents Microbial Sensitivity Tests Crystallography X-Ray Stereocenter Antituberculosis activity Anti-Infective Agents Drug Discovery Spectroscopy Fourier Transform Infrared Humans Chirality Nitrogen Compounds Pharmacology biology Molecular Structure Cytotoxic activity Chemistry Biological activity Crystal structure Organic Chemistry General Medicine Nuclear magnetic resonance spectroscopy DNA Phosphorus Compounds biology.organism_classification Heteronuclear molecule Asa-cyclotetraphosphazenes MCF-7 Cells Racemic mixture Chirality (chemistry) Heteronuclear single quantum coherence spectroscopy |
| Popis: | WOS: 000363431300061 PubMed: 25305333 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, H-1, C-13{H-1} and P-31{H-1} 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 P-31{H-1}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. (c) 2014 Elsevier Masson SAS. All rights reserved. Turkish Academy of Sciences (TUBA)Turkish Academy of Sciences; Scientific and Technical Research Council of TurkeyTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [211T019] The authors thank the "Scientific and Technical Research Council of Turkey" (Grant No. 211T019), "Medicinal Plants and Medicine Research Center of Anadolu University, Eskisehir, Turkey" for the use of their X-ray facilities, and Z. K. thanks Turkish Academy of Sciences (TUBA) for partial support. |
| Databáze: | OpenAIRE |
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