Phosphorus-nitrogen compounds: Part 28. Syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing vanillinato and pendant ferrocenyl groups

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dc.authoridDundar, Devrim/0000-0003-2073-7168
dc.authoridAsmafiliz, Nuran/0000-0002-9335-4101
dc.authoridHokelek, Tuncer/0000-0002-8602-4382
dc.authoridgonder, lutfiye yasemin/0000-0001-6849-3364
dc.contributor.authorTumer, Yasemin
dc.contributor.authorAsmafiliz, Nuran
dc.contributor.authorKilic, Zeynel
dc.contributor.authorHokelek, Tuncer
dc.contributor.authorKoc, L. Yasemin
dc.contributor.authorAcik, Leyla
dc.contributor.authorYola, Mehmet Lutfi
dc.date.accessioned2024-09-29T16:00:26Z
dc.date.available2024-09-29T16:00:26Z
dc.date.issued2013
dc.departmentKarabük Üniversitesien_US
dc.description.abstractThe gradually Cl replacement reactions of spirocyclic mono (1 and 2) and bisferrocenyl cyclotriphosphazenes (3-5) with the potassium salt of 4-hydroxy-3-methoxybenzaldehyde (potassium vanillinate) gave mono (1a-5a), geminal (gem-1b-5b), non-geminal (cis-1b, cis-5b and trans-2b-5b), tri (1c-5c) and tetra-substituted phosphazenes (1d-5d). Some phosphazenes have stereogenic P-center(s). The chirality of 4c was verified using chiral HPLC column. Electrochemical behaviors were influenced only by the number of ferrocene groups, but not the length of the amine chains and the substituent(s). The structures of the new phosphazenes were determined by FTIR, MS, H-1, C-13 and P-31 NMR, HSQC and HMBC spectral data. The solid-state structures of cis-1b and 4d were examined by single crystal X-ray diffraction techniques. The twelve phosphazene derivatives were screened for antimicrobial activity and the compounds 5a, cis-1b and 2c exhibited the highest antibacterial activity against G(+) and G(-) bacteria. In addition, it was found that overall gem-1b inhibited the growth of Mycobacterium tuberculosis. The compounds 1d, 2d and 4d were tested in HeLa cancer cell lines. Among these compounds, 2d had cytotoxic effect on HeLa cell in the first 48 h. Moreover, interactions between compounds 2a, gem-1b, gem-2b, cis-1b, 2c, 3c, 4c, 5c, 1d, 2d and 4d, and pBR322 plasmid DNA were investigated. (c) 2013 Elsevier B.V. All rights reserved.en_US
dc.description.sponsorshipScientific and Technical Research Council of Turkey [112T043]en_US
dc.description.sponsorshipThe authors acknowledge the Scientific and Technical Research Council of Turkey Grant No. 112T043.en_US
dc.identifier.doi10.1016/j.molstruc.2013.06.036
dc.identifier.endpage124en_US
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-84880183372en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage112en_US
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2013.06.036
dc.identifier.urihttps://hdl.handle.net/20.500.14619/5123
dc.identifier.volume1049en_US
dc.identifier.wosWOS:000324784700014en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevieren_US
dc.relation.ispartofJournal of Molecular Structureen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectFerrocenylphosphazenesen_US
dc.subjectSpectroscopyen_US
dc.subjectElectrochemistryen_US
dc.subjectAntituberculosis activityen_US
dc.subjectHeLa cell lineen_US
dc.titlePhosphorus-nitrogen compounds: Part 28. Syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing vanillinato and pendant ferrocenyl groupsen_US
dc.typeArticleen_US

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