Non-inclusion complexes between riboflavin and cyclodextrins

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dc.contributor.authorde Jesus, Marcelo Bispo
dc.contributor.authorFraceto, Leonardo Fernandes [UNESP]
dc.contributor.authorFlorencia Martini, Maria
dc.contributor.authorPickholz, Monica
dc.contributor.authorFerreira, Carmen Verissima
dc.contributor.authorde Paula, Eneida
dc.contributor.institutionUniversidade Estadual de Campinas (UNICAMP)
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionUniv Buenos Aires
dc.contributor.institutionConsejo Nacl Invest Cient & Tecn
dc.date.accessioned2014-05-20T13:12:11Z
dc.date.available2014-05-20T13:12:11Z
dc.date.issued2012-06-01
dc.description.abstractObjectives To investigate the molecular interaction between beta-cyclodextrin (beta CD) or hydroxypropyl-beta-cyclodextrin (HP beta CD) and riboflavin (RF), and to test the anticancer potential of these formulations. Methods The physicochemical characterization of the association between RF and CDs was performed by UV-vis absorption, fluorescence, differential scanning calorimetry and NMR techniques. Molecular dynamics simulation was used to shed light on the mechanism of interaction of RF and CDs. Additionally, in-vitro cell culture tests were performed to evaluate the cytotoxicity of the RFCD complexes against prostate cancer cells. Key findings Neither beta CD nor HP beta CD led to substantial changes in the physicochemical properties of RF (with the exception of solubility). Additionally, rotating frame Overhauser effect spectroscopy experiments detected no spatial correlations between hydrogens from the internal cavity of CDs and RF, while molecular dynamics simulations revealed out-of-ring RFCD interactions. Notwithstanding, both RF beta CD and RFHP beta CD complexes were cytotoxic to PC3 prostate cancer cells. Conclusions The interaction between RF and either beta CD or HP beta CD, at low concentrations, seems to be made through hydrogen bonding between the flavonoid and the external rim of both CDs. Regardless of the mechanism of complexation, our findings indicate that RFCD complexes significantly increase RF solubility and potentiate its antitumour effect.en
dc.description.affiliationUniv Estadual Campinas, Dept Biochem, Inst Biol, UNICAMP, BR-13083970 Campinas, SP, Brazil
dc.description.affiliationState Univ São Paulo, UNESP, Dept Environm Engn, Sorocaba, Brazil
dc.description.affiliationUniv Buenos Aires, Dept Pharmaceut Technol, Fac Pharm & Biochem, RA-1053 Buenos Aires, DF, Argentina
dc.description.affiliationConsejo Nacl Invest Cient & Tecn, RA-1033 Buenos Aires, DF, Argentina
dc.description.affiliationUnespState Univ São Paulo, UNESP, Dept Environm Engn, Sorocaba, Brazil
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.description.sponsorshipConsejo Nacional de Investigaciones Científicas y Técnicas (CONICET)
dc.description.sponsorshipIdFAPESP: 06/03838-1
dc.format.extent832-842
dc.identifierhttp://dx.doi.org/10.1111/j.2042-7158.2012.01492.x
dc.identifier.citationJournal of Pharmacy and Pharmacology. Malden: Wiley-blackwell, v. 64, n. 6, p. 832-842, 2012.
dc.identifier.doi10.1111/j.2042-7158.2012.01492.x
dc.identifier.issn0022-3573
dc.identifier.urihttp://hdl.handle.net/11449/177
dc.identifier.wosWOS:000303858200008
dc.language.isoeng
dc.publisherWiley-Blackwell
dc.relation.ispartofJournal of Pharmacy and Pharmacology
dc.relation.ispartofjcr2.309
dc.relation.ispartofsjr0,657
dc.rights.accessRightsAcesso restrito
dc.sourceWeb of Science
dc.subjectcyclodextrinen
dc.subjectNMRen
dc.subjectnon-inclusion complexen
dc.subjectprostate canceren
dc.subjectriboflavinen
dc.titleNon-inclusion complexes between riboflavin and cyclodextrinsen
dc.typeArtigo
dcterms.licensehttp://olabout.wiley.com/WileyCDA/Section/id-406071.html
dcterms.rightsHolderWiley-blackwell
unesp.author.orcid0000-0002-1949-9310[3]
unesp.author.orcid0000-0003-0812-1491[1]
unesp.author.orcid0000-0002-2827-2038[2]
unesp.campusUniversidade Estadual Paulista (Unesp), Instituto de Ciência e Tecnologia, Sorocabapt

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