Study of the interaction between hydroxymethylnitrofurazone and 2-hydroxypropyl-beta-cyclodextrin

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dc.contributor.authorGrillo, Renato [UNESP]
dc.contributor.authorde Melo, Nathalie F. S. [UNESP]
dc.contributor.authorMoraes, Carolina Morales
dc.contributor.authorde Lima, Renata
dc.contributor.authorMenezes, Carla M. S.
dc.contributor.authorFerreira, Elizabeth Igne
dc.contributor.authorRosa, Andre Henrique [UNESP]
dc.contributor.authorFraceto, Leonardo Fernandes [UNESP]
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionUniversidade Estadual de Campinas (UNICAMP)
dc.contributor.institutionUniversidade de São Paulo (USP)
dc.date.accessioned2014-05-20T15:33:28Z
dc.date.available2014-05-20T15:33:28Z
dc.date.issued2008-06-09
dc.description.abstractChagas disease is a serious health problem in Latin America. Hidroxymethylnitrofurazone (NFOH) is a nitrofurazone prodrug more active than nitrofurazone against Trypanosoma cruzi. However, NFOH presents low aqueous solubility, high photodecomposition and high toxicity. The present work is focused on the characterization of an inclusion complex of NFOH in 2-hydroxypropyl-beta-cyclodextrin (HP-beta-CD). The complexation with HP-beta-CD was investigated using reversed-phase liquid chromatography, solubility isotherms and nuclear magnetic resonance. The retention behavior was analyzed on a reversed-phase C-18 column, using acetonitrile-water (20/80, v/v) as the mobile phase, in which HP-beta-CD was incorporated as a mobile phase additive. The decrease in the retention times with increasing concentrations of HP-beta-CD enables the determination of the apparent stability constant of the complex (K = 6.2 +/- 0.3 M-1) by HPLC. The solubility isotherm was studied and the value for the apparent stability constant (K = 7.9 +/- 0.2 M-1) was calculated. The application of continuous variation method indicated the presence of a complex with 1:1 NFOH:HP-beta-CD stoichiometry. The photostability study showed that the formation of an inclusion complex had a destabilizing effect on the photodecomposition of NFOH when compared to that of the "free" molecule in solution. The mobility investigation (by NMR longitudinal relaxation time) gives information about the complexation of NFOH with HP-beta-CD. In preliminary toxicity studies, cell viability tests revealed that inclusion complexes were able to decrease the toxic effect (p < 0.01) caused by NFOH. (c) 2008 Elsevier B.V. All rights reserved.en
dc.description.affiliationUniv Estadual Paulista, BR-18087180 São Paulo, Brazil
dc.description.affiliationUniv Estadual Campinas, Inst Biol, Dept Bioquim, São Paulo, Brazil
dc.description.affiliationUniv São Paulo, Fac Ciencias Farmaceut, LAPEN, BR-09500900 São Paulo, Brazil
dc.description.affiliationUnespUniv Estadual Paulista, BR-18087180 São Paulo, Brazil
dc.format.extent295-302
dc.identifierhttp://dx.doi.org/10.1016/j.jpba.2008.01.010
dc.identifier.citationJournal of Pharmaceutical and Biomedical Analysis. Oxford: Pergamon-Elsevier B.V. Ltd, v. 47, n. 2, p. 295-302, 2008.
dc.identifier.doi10.1016/j.jpba.2008.01.010
dc.identifier.issn0731-7085
dc.identifier.lattes2188736885721242
dc.identifier.orcid0000-0002-2042-018X
dc.identifier.orcid0000-0002-0284-5782
dc.identifier.urihttp://hdl.handle.net/11449/42076
dc.identifier.wosWOS:000256649400010
dc.language.isoeng
dc.publisherPergamon-Elsevier B.V. Ltd
dc.relation.ispartofJournal of Pharmaceutical and Biomedical Analysis
dc.relation.ispartofjcr2.831
dc.relation.ispartofsjr0,919
dc.rights.accessRightsAcesso restrito
dc.sourceWeb of Science
dc.subjecthydroxymethylnitrofurazoneen
dc.subject2-hydroxypropyl-beta-cyclodextrinen
dc.subjectsolubility isothermen
dc.subjectnuclear magnetic resonanceen
dc.subjecttoxicityen
dc.titleStudy of the interaction between hydroxymethylnitrofurazone and 2-hydroxypropyl-beta-cyclodextrinen
dc.typeArtigo
dcterms.licensehttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
dcterms.rightsHolderPergamon-Elsevier B.V. Ltd
unesp.author.lattes5228846314663888[7]
unesp.author.lattes2188736885721242[1]
unesp.author.orcid0000-0002-2042-018X[7]
unesp.author.orcid0000-0002-0284-5782[1]
unesp.campusUniversidade Estadual Paulista (Unesp), Instituto de Ciência e Tecnologia, Sorocabapt

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