Syntheses, spectroscopic and crystallographic characterizations of cis- and trans-dispirocyclic ferrocenylphosphazenes: molecular dockings, cytotoxic and antimicrobial activities

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dc.contributor.authorTumer, Yasemin
dc.contributor.authorAsmafiliz, Nuran
dc.contributor.authorZeyrek, C. Tugrul
dc.contributor.authorKilic, Zeynel
dc.contributor.authorAcik, Leyla
dc.contributor.authorCelik, S. Pinar
dc.contributor.authorHokelek, Tuncer
dc.date.accessioned2020-06-25T18:29:43Z
dc.date.available2020-06-25T18:29:43Z
dc.date.issued2018
dc.departmentKırıkkale Üniversitesi
dc.descriptionHokelek, Tuncer/0000-0002-8602-4382; Unver, Huseyin/0000-0003-3968-4385; Asmafiliz, Nuran/0000-0002-9335-4101; Tumer, Yasemin/0000-0002-2460-9414
dc.description.abstractNew cis-(4-6) and trans-dispirocyclic ferrocenylphosphazene derivatives (7-9) were obtained by reactions of hexachlorocyclotriphosphazene (N3P3Cl6) with N-alkyl-N-monoferrocenyldiamines of the formula FcCH(2)NH(CH2)(n)NHR [n = 2, R = CH3 (1); n = 2, R = C2H5 (2) and n = 3, R = CH3 (3)]. Characterizations of the products were performed using MS, FTIR, H-1, C-13 and P-31 NMR techniques. The crystal structures of 5 (with 8), 6, 7 and 9 were determined by X-ray crystallography. The most important result of this study was that the trans chiral phosphazenes crystallized as only one enantiomer. Studies of the antibacterial and antifungal activity of the phosphazenes (4-9) showed that compounds 6 and 7 were effective against P. vulgaris and K. pneumoniae. The cytotoxic activities of 4-9 against L929 fibroblasts and DLD-1 colon cancer cells were investigated. The necrotic effects of 4 and 7 were greater in the DLD-1 cell line than those in the L929 cell line. DFT calculations were carried out using the B3LYP functional with the LANL2DZ basis set to determine the energies, the orientations of the molecular orbitals (HOMOs and LUMOs) and the molecular electrostatic potential (MEP) surfaces of the partly substituted cyclotriphos-phazenes (6, 7 and 9). The results for 6, 7 and 9 revealed that these bonded to the active sites of A-DNA and B-DNA by weak non-covalent interactions, which was also supported by molecular docking investigations.en_US
dc.description.sponsorshipScientific and Technical Research Council of TurkeyTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [216Z182]; Turkish Academy of Sciences (TUBA)Turkish Academy of Sciences; Hacettepe University Scientific Research Project UnitHacettepe University [013 D04 602 004]en_US
dc.description.sponsorshipThe authors acknowledge the Scientific and Technical Research Council of Turkey Grant No. 216Z182. The authors also acknowledge the Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer. Z. K. thanks the Turkish Academy of Sciences (TUBA) for partial support of this work. T. H. is grateful to the Hacettepe University Scientific Research Project Unit (Grant No. 013 D04 602 004).en_US
dc.identifier.citationclosedAccessen_US
dc.identifier.doi10.1039/c7nj03643d
dc.identifier.endpage1756en_US
dc.identifier.issn1144-0546
dc.identifier.issn1369-9261
dc.identifier.issue3en_US
dc.identifier.scopus2-s2.0-85041372424
dc.identifier.scopusqualityQ2
dc.identifier.startpage1740en_US
dc.identifier.urihttps://doi.org/10.1039/c7nj03643d
dc.identifier.urihttps://hdl.handle.net/20.500.12587/7436
dc.identifier.volume42en_US
dc.identifier.wosWOS:000423702900026
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherRoyal Soc Chemistryen_US
dc.relation.ispartofNew Journal Of Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.titleSyntheses, spectroscopic and crystallographic characterizations of cis- and trans-dispirocyclic ferrocenylphosphazenes: molecular dockings, cytotoxic and antimicrobial activitiesen_US
dc.typeArticle

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