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

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dc.authoridAsmafiliz, Nuran/0000-0002-9335-4101
dc.authoridgonder, lutfiye yasemin/0000-0001-6849-3364
dc.authoridHokelek, Tuncer/0000-0002-8602-4382
dc.contributor.authorTumer, Yasemin
dc.contributor.authorKoc, L. Yasemin
dc.contributor.authorAsmafiliz, Nuran
dc.contributor.authorKilic, Zeynel
dc.contributor.authorHokelek, Tuncer
dc.contributor.authorSoltanzade, Hossien
dc.contributor.authorAcik, Leyla
dc.date.accessioned2025-03-23T19:44:34Z
dc.date.available2025-03-23T19:44:34Z
dc.date.issued2015
dc.departmentSinop Üniversitesi
dc.description.abstractThe 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, H-1, C-13{H-1} and P-31{H-1} 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 A mu M concentration, taking into account the MIC values. Besides, interactions between the phosphazenes and pBR322 plasmid DNA were also investigated. The vanillinato cyclotriphosphazenes containing pendant monoferrocenyl arms were obtained. Some of the phosphazenes were tested against HeLa cancer cells. The new phosphazenes were screened for antimicrobial activity, and interactions between the phosphazenes and pBR322 plasmid DNA were evaluated. The spectral characterizations of all the phosphazenes were presented.
dc.description.sponsorshipScientific and Technical Research Council of Turkey [112T043]; Hacettepe University, Scientific Research Unit [02 02 602002]
dc.description.sponsorshipThe authors acknowledge the Scientific and Technical Research Council of Turkey Grant No. 112T043. T.H. is indebted to Hacettepe University, Scientific Research Unit (Grant No. 02 02 602002) for the financial support.
dc.identifier.doi10.1007/s00775-014-1223-5
dc.identifier.endpage178
dc.identifier.issn0949-8257
dc.identifier.issn1432-1327
dc.identifier.issue1
dc.identifier.pmid25491284
dc.identifier.scopus2-s2.0-84925510821
dc.identifier.scopusqualityQ2
dc.identifier.startpage165
dc.identifier.urihttps://doi.org/10.1007/s00775-014-1223-5
dc.identifier.urihttps://hdl.handle.net/11486/6968
dc.identifier.volume20
dc.identifier.wosWOS:000347407700014
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherSpringer
dc.relation.ispartofJournal of Biological Inorganic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectFerrocenylphosphazenes
dc.subjectAntimicrobial activity
dc.subjectDNA interaction
dc.subjectCytotoxicity
dc.subjectSpectroscopy
dc.titlePhosphorus-nitrogen compounds: part 30. Syntheses and structural investigations, antimicrobial and cytotoxic activities and DNA interactions of vanillinato-substituted NN or NO spirocyclic monoferrocenyl cyclotriphosphazenes
dc.typeArticle

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