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.authoridAsmafiliz, Nuran/0000-0002-9335-4101
dc.authoridHokelek, Tuncer/0000-0002-8602-4382
dc.authoridDundar, Devrim/0000-0003-2073-7168
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.accessioned2025-03-23T19:40:50Z
dc.date.available2025-03-23T19:40:50Z
dc.date.issued2013
dc.departmentSinop Üniversitesi
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.
dc.description.sponsorshipScientific and Technical Research Council of Turkey [112T043]
dc.description.sponsorshipThe authors acknowledge the Scientific and Technical Research Council of Turkey Grant No. 112T043.
dc.identifier.doi10.1016/j.molstruc.2013.06.036
dc.identifier.endpage124
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-84880183372
dc.identifier.scopusqualityQ1
dc.identifier.startpage112
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2013.06.036
dc.identifier.urihttps://hdl.handle.net/11486/6425
dc.identifier.volume1049
dc.identifier.wosWOS:000324784700014
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectFerrocenylphosphazenes
dc.subjectSpectroscopy
dc.subjectElectrochemistry
dc.subjectAntituberculosis activity
dc.subjectHeLa cell line
dc.titlePhosphorus-nitrogen compounds: Part 28. Syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing vanillinato and pendant ferrocenyl groups
dc.typeArticle

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