Formation of the inclusion complex of water soluble fluorescent calix[4]arene and naringenin: solubility, cytotoxic effect and molecular modeling studies

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dc.contributor.authorOğuz, Mehmet
dc.contributor.authorBhatti, Asıf Ali
dc.contributor.authorDoğan, Berna
dc.contributor.authorKarakurt, Serdar
dc.contributor.authorDurdagı, Serdar
dc.contributor.authorYılmaz, Mustafa
dc.date.accessioned2020-03-26T20:19:46Z
dc.date.available2020-03-26T20:19:46Z
dc.date.issued2019
dc.departmentSelçuk Üniversitesi, Fen Fakültesi, Kimya Bölümüen_US
dc.description.abstractNaringenin is considered as an important flavonoid in phytochemistry because of its important effect on cancer chemoprevention. Unfortunately its poor solubility has restricted its therapeutic applications. In this study, an efficient water-soluble fluorescent calix[4]arene (compound 5) was synthesized as host macromolecule to increase solubility and cytotoxicity in cancer cells of water-insoluble naringenin as well as to clarify localization of naringenin into the cells. Complex formed by host–guest interaction between compound 5 and naringenin was analyzed with UV–visible, fluorescence, FTIR spectroscopic techniques and molecular modeling studies. Stern–Volmer analysis showed binding constant value of Ksv 3.5 × 107 M?1 suggesting strong interaction between host and guest. Binding capacity shows 77% of naringenin was loaded on compound 5. Anticarcinogenic effects of naringenin complex were evaluated on human colorectal carcinoma cells (DLD-1) and it was found that 5-naringenin complex inhibits proliferation of DLD-1 cells 3.4-fold more compared to free naringenin. Fluorescence imaging studies show 5-naringenin complex was accumulated into the cytoplasm instead of the nucleus. Increased solubility and cytotoxicity of naringenin with fluorescent calix[4]arene makes it one of the potential candidates as a therapeutic enhancer. For deep understanding of host–guest interaction mechanisms, complementary multiscale molecular modeling studies were also carried out. Communicated by Ramaswamy H. Sarma. © 2019, © 2019 Informa UK Limited, trading as Taylor & Francis Group.en_US
dc.identifier.citationOğuz, M., Bhatti, A.A., Doğan, B., Karakurt, S., Durdagı, S., Yılmaz, M. (2019). Formation of the Inclusion Complex of Water Soluble Fluorescent Calix[4]Arene and Naringenin: Solubility, Cytotoxic Effect and Molecular Modeling Studies. Journal of Biomolecular Structure and Dynamics, 38,(13), 3801-3813.
dc.identifier.doi10.1080/07391102.2019.1668301en_US
dc.identifier.issn0739-1102en_US
dc.identifier.pmid31526236en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://dx.doi.org/10.1080/07391102.2019.1668301
dc.identifier.urihttps://hdl.handle.net/20.500.12395/38397
dc.identifier.wosWOS:000558542300005en_US
dc.identifier.wosqualityN/Aen_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.institutionauthorOğuz, Mehmet
dc.institutionauthorBhatti, Asıf Ali
dc.institutionauthorKarakurt, Serdar
dc.institutionauthorYılmaz, Mustafa
dc.language.isoenen_US
dc.publisherTaylor and Francis Ltd.en_US
dc.relation.ispartofJournal of Biomolecular Structure and Dynamicsen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.selcuk20240510_oaigen_US
dc.subjectcalix[4]arenesen_US
dc.subjectcytotoxicityen_US
dc.subjectfluorescenceen_US
dc.subjectinclusion complexesen_US
dc.subjectmolecular dockingen_US
dc.subjectnaringeninen_US
dc.subjectsolubilizationen_US
dc.subjectWater solubleen_US
dc.titleFormation of the inclusion complex of water soluble fluorescent calix[4]arene and naringenin: solubility, cytotoxic effect and molecular modeling studiesen_US
dc.typeArticleen_US

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