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.contributor.authorİşcan, Özlem
dc.contributor.authorCemaloğlu, Reşit
dc.contributor.authorAsmafiliz, Nuran
dc.contributor.authorZeyrek, Celal Tuğrul
dc.contributor.authorKılıç, Zeynel
dc.contributor.authorAçık, Leyla
dc.contributor.authorAydın, Betül
dc.date.accessioned2025-01-21T16:28:13Z
dc.date.available2025-01-21T16:28:13Z
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. Graphic abstract: [Figure not available: see fulltext.] © 2021, The Author(s), under exclusive licence to Springer Nature Switzerland AG.
dc.description.sponsorshipTÜBA; Türkiye Bilimsel ve Teknolojik Araştirma Kurumu, TÜBITAK, (116Z400); Türkiye Bilimler Akademisi; Hacettepe Üniversitesi, (013 D04 602 004)
dc.identifier.doi10.1007/s11030-021-10231-5
dc.identifier.endpage1100
dc.identifier.issn1381-1991
dc.identifier.issue2
dc.identifier.pmid33988806
dc.identifier.scopus2-s2.0-85105929321
dc.identifier.scopusqualityQ1
dc.identifier.startpage1077
dc.identifier.urihttps://doi.org/10.1007/s11030-021-10231-5
dc.identifier.urihttps://hdl.handle.net/20.500.12587/23512
dc.identifier.volume26
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherSpringer Science and Business Media Deutschland GmbH
dc.relation.ispartofMolecular Diversity
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_20241229
dc.subjectAntimicrobial activity; Crystal structure; Cytotoxicity; DFT calculations; Molecular docking; Mono- and dispirocyclotriphosphazenes
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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