Phosphorus-nitrogen compounds: Part 31. Syntheses, structural and stereogenic properties, in vitro cytotoxic and antimicrobial activities, and DNA interactions of bicyclotetraphosphazenes containing bulky side group

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dc.contributor.authorMutlu, Gurcu
dc.contributor.authorElmas, Gamze
dc.contributor.authorKilic, Zeynel
dc.contributor.authorHokelek, Tuncer
dc.contributor.authorKoc, L. Yasemin
dc.contributor.authorTurk, Mustafa
dc.contributor.authorDal, Hakan
dc.date.accessioned2020-06-25T18:12:56Z
dc.date.available2020-06-25T18:12:56Z
dc.date.issued2015
dc.departmentKırıkkale Üniversitesi
dc.descriptionAydin, Betul/0000-0002-9092-1350; Hokelek, Tuncer/0000-0002-8602-4382
dc.description.abstractHexachlorocyclotriphosphazene, N3P3Cl6, and octachlorocyclotetraphosphazene, N4P4Cl8, were reacted with K2N2O2 salt of symmetric tetradentate ligand to obtain spiro-bino-spiro [(sbs) (2)] and 2,6-spiro-ansa-spiro [(2,6-sas) (3)] phosphazenes, respectively. The sbs was obtained in a very poor yield, whereas, 2,6-sas was obtained in a moderate yield. The derivatives of 2,6-sas with mono-and diamines were synthesized. When the reactions were carried out, one equimolar amount of 2,6-sas with an excess pyrrolidine, piperidine, morpholine, 1,4-dioxa-8-azaspiro[4,5]decane (DASD), N-methylethane1,2-diamine, N-ethylethane-1,2-diamine and N-methylpropane-1,3-diamine, along with the fully substituted 2,6-sas-cyclotetraphosphazene derivatives (4a, 4b and 5a-7a), were prepared. However, the excess morpholine and DASD with 2,6-sas yielded the geminal bis-(4c and 4e) and tris- (4d and 4f) cyclotetraphosphazenes, respectively. The Cl replacement reaction of 2,6-sas with one equimolar amount of 7 led to the formation of partly substituted 2,6-sas (7b). The structures of the compounds were verified by elemental analyses, MS, FTIR, H-1, C-13{H-1}, P-31 NMR, HSQC, HMBC and X-ray crystallography (for 3 and 4a) techniques. All the 2,6-sas cyclotetraphosphazenes (except 3, 4a and 4b) have stereogenic P-atoms. All the compounds were screened for antibacterial and antifungal activities against bacteria and yeast strains. The interactions of the compounds with supercoiled plasmid pBR322 DNA were investigated. The evaluations for cytotoxic activity, and apoptotic and necrotic effects against A549 lung cancer and L929 fibroblast cell lines were introduced. (C) 2015 Elsevier B.V. All rights reserved.en_US
dc.description.sponsorshipScientific and Technical Research Council of TurkeyTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [211T019]; Turkish Academy of Sciences (TUBA)Turkish Academy of Sciencesen_US
dc.description.sponsorshipThe authors thank the "Scientific and Technical Research Council of Turkey'' (Grant No. 211T019), and Z.K. thanks Turkish Academy of Sciences (TUBA) for partial support.en_US
dc.identifier.citationclosedAccessen_US
dc.identifier.doi10.1016/j.ica.2015.07.027
dc.identifier.endpage81en_US
dc.identifier.issn0020-1693
dc.identifier.issn1873-3255
dc.identifier.scopus2-s2.0-84938854593
dc.identifier.scopusqualityQ2
dc.identifier.startpage69en_US
dc.identifier.urihttps://doi.org/10.1016/j.ica.2015.07.027
dc.identifier.urihttps://hdl.handle.net/20.500.12587/6081
dc.identifier.volume436en_US
dc.identifier.wosWOS:000361187700010
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier Science Saen_US
dc.relation.ispartofInorganica Chimica Acta
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectBicyclotetraphosphazenesen_US
dc.subjectSpectroscopyen_US
dc.subjectStereogenismen_US
dc.subjectCytotoxicityen_US
dc.subjectDNA bindingen_US
dc.subjectCrystallographyen_US
dc.titlePhosphorus-nitrogen compounds: Part 31. Syntheses, structural and stereogenic properties, in vitro cytotoxic and antimicrobial activities, and DNA interactions of bicyclotetraphosphazenes containing bulky side groupen_US
dc.typeArticle

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