Phosphorus-nitrogen compounds: part 53-synthesis, characterization, cytotoxic and antimicrobial activity, DNA interaction and molecular docking studies of new mono- and dispirocyclotriphosphazenes with pendant arm(s)

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dc.authoridZeyrek, Celal Tugrul/0000-0001-6744-7841
dc.authoridAydin, Betul/0000-0002-9092-1350
dc.authoridAcik, Leyla/0000-0002-3672-8429
dc.authorid, RESIT/0000-0002-2802-0754
dc.authoridIscan, Ozlem/0000-0003-3282-1121
dc.authoridHokelek, Tuncer/0000-0002-8602-4382
dc.contributor.authorIscan, Ozlem
dc.contributor.authorCemaloglu, Resit
dc.contributor.authorAsmafiliz, Nuran
dc.contributor.authorZeyrek, Celal Tugrul
dc.contributor.authorKilic, Zeynel
dc.contributor.authorAcik, Leyla
dc.contributor.authorAydin, Betul
dc.date.accessioned2025-01-21T16:43:26Z
dc.date.available2025-01-21T16:43:26Z
dc.date.issued2022
dc.departmentKırıkkale Üniversitesi
dc.description.abstractMono-/dispirocyclotriphosphazenes with pendant arm(s) are robust, but they are less investigated inorganic ring systems. In this study, a series of mono (3 and 4)- and dispirocyclotriphosphazenes with 4-chloro-benzyl pendant arm(s) (13-16) was obtained from the Cl exchange reactions of hexachlorocyclotriphosphazene with sodium (N-benzyl)aminopropanoxides (1 and 2). When compound (3) reacted with excess pyrrolidine, morpholine, tetra-1,4-dioxa-8-azaspiro[4,5]decane (DASD) and piperidine, the fully substituted monospirocyclotriphosphazenes (7, 9, 10 and 12) occurred. But, the reactions of 4 with excess piperidine and morpholine produced the gem-piperidino (5)- and morpholino (6)-substituted monospirocyclotriphosphazenes, whereas the reactions of 4 with excess pyrrolidine and DASD gave the fully substituted monospirocyclotriphosphazenes (8) and (11). However, it should be indicated that these derivatives were obtained to be used for the investigation of their spectral, stereogenic and biological properties. The structures of 5, 7 and 14 were determined crystallographically. X-ray data of 5 and 14 displayed that both of compounds were chiral in solid state, and their absolute configurations were assigned as R and RR. Additionally, the antimicrobial activities of phosphazenes were investigated. Minimum inhibitory concentrations, minimal bacterial concentrations and minimum fungicidal concentrations of phosphazenes were determined. The interactions of phosphazenes with plasmid DNA were evaluated by agarose gel electrophoresis. The cytotoxic activities of compounds were studied against L929 fibroblast and DLD-1 colon cancer cells. In addition, density functional theory calculations of 5, 7 and 14 were reported, and their molecular docking studies with DNA, E. coli DNA gyrase and topoisomerase IV were presented.
dc.description.sponsorshipScientific and Technical Research Council of Turkey [116Z400]; Turkish Academy of Sciences (TuBA); Hacettepe University Scientific Research Project Unit [013 D04 602 004]
dc.description.sponsorshipThe authors acknowledge the Scientific and Technical Research Council of Turkey Grant No.116Z400. Z. K. thanks the Turkish Academy of Sciences (TuBA) for partial support of this work. T. H. is grateful to Hacettepe University Scientific Research Project Unit (Grant No. 013 D04 602 004). The numerical calculations reported in this paper were fully/partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).
dc.identifier.doi10.1007/s11030-021-10231-5
dc.identifier.endpage1100
dc.identifier.issn1381-1991
dc.identifier.issn1573-501X
dc.identifier.issue2
dc.identifier.pmid33988806
dc.identifier.startpage1077
dc.identifier.urihttps://doi.org/10.1007/s11030-021-10231-5
dc.identifier.urihttps://hdl.handle.net/20.500.12587/25269
dc.identifier.volume26
dc.identifier.wosWOS:000650521700001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherSpringer
dc.relation.ispartofMolecular Diversity
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_20241229
dc.subjectMono; and dispirocyclotriphosphazenes; Crystal structure; Antimicrobial activity; Cytotoxicity; DFT calculations; Molecular docking
dc.titlePhosphorus-nitrogen compounds: part 53-synthesis, characterization, cytotoxic and antimicrobial activity, DNA interaction and molecular docking studies of new mono- and dispirocyclotriphosphazenes with pendant arm(s)
dc.typeArticle

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