Preparation and characterization of a synthetic curcumin analog inclusion complex and preliminary evaluation of in vitro antileishmanial activity

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MetadadosDescriçãoIdioma
Autor(es): dc.creatorPinto, Luciana Matos Alves-
Autor(es): dc.creatorAdeoye, Oluwatomide-
Autor(es): dc.creatorThomasi, Sérgio Scherrer-
Autor(es): dc.creatorFrancisco, Ana Paula-
Autor(es): dc.creatorCarvalheiro, Manuela Colla-
Autor(es): dc.creatorCabral-Marques, Helena-
Data de aceite: dc.date.accessioned2026-02-09T11:47:13Z-
Data de disponibilização: dc.date.available2026-02-09T11:47:13Z-
Data de envio: dc.date.issued2021-09-02-
Data de envio: dc.date.issued2021-09-02-
Data de envio: dc.date.issued2020-11-14-
Fonte completa do material: dc.identifierhttps://repositorio.ufla.br/handle/1/48027-
Fonte completa do material: dc.identifierhttps://www.sciencedirect.com/science/article/abs/pii/S0378517320307481#!-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/capes/1147440-
Descrição: dc.descriptionThe aim of this work was to prepare and characterize inclusion complexes between a synthetic curcumin analog (dibenzalacetone, DBA) and beta-cyclodextrin (β-CD); and to evaluate their in vitro antileishmanial activity. DBA was synthetized and characterized by spectroscopic methods and the inclusion complexes were obtained by kneading and lyophilization (LIO) in 1:1 and 1:2 stoichiometries. Phase solubility and dissolution assays showed a 40-fold increase in the aqueous solubility of DBA and its complete dissolution from LIO 1:1 formulation after 120 min respectively. Solid-state characterization by differential scanning calorimetry and near infrared spectroscopy demonstrated the inclusion of DBA in the β-CD cavity at the molar ratios tested, with LIO 1:1 formulation being the most stable. Using nuclear magnetic resonance experiments, the protons inside the cavity of β-CD were the most affected after the inclusion of DBA molecule. The cellular viability of THP-1 macrophage cells treated with plain DBA, β-CD and DBA/CD inclusion complexes showed that the plain DBA and DBA/CD at 1:2 stoichiometry presented toxicity, while β-CD alone and DBA/CD at 1:1 stoichiometry showed no toxicity up to 640 μg mL−1. The in vitro assay with free-living promastigotes demonstrated that plain DBA and β-CD had IC50 of < 10 and > 320 μg mL−1 respectively, while only inclusion complexes with 1:1 stoichiometry showed antiproliferative activity with IC50 = 51.3 μg mL−1. Using the amastigote intracellular forms, there was also a difference between the plain and β-CD complexed DBA with complexes of 1:1 and 1:2 stoichiometry presenting EC50 = 66.3 μg mL−1 and 58.9 μg mL−1 respectively. The study concluded that DBA/CD at 1:1 molar ratio has the potential to decrease the intrinsic toxicity of plain DBA towards Leishmania host cells, which may be a therapeutic advantage in the application of these compounds.-
Idioma: dc.languageen-
Publicador: dc.publisherElsevier-
Direitos: dc.rightsrestrictAccess-
???dc.source???: dc.sourceInternational Journal of Pharmaceutics-
Palavras-chave: dc.subjectBeta-cyclodextrin-
Palavras-chave: dc.subjectDibenzalacetone-
Palavras-chave: dc.subjectCurcumin-
Palavras-chave: dc.subjectLeishmania major-
Palavras-chave: dc.subjectLeishmaniasis-
Palavras-chave: dc.subjectBeta-ciclodextrina-
Palavras-chave: dc.subjectDibenzalacetona-
Palavras-chave: dc.subjectCurcumina-
Palavras-chave: dc.subjectLeishmaniose-
Título: dc.titlePreparation and characterization of a synthetic curcumin analog inclusion complex and preliminary evaluation of in vitro antileishmanial activity-
Tipo de arquivo: dc.typeArtigo-
Aparece nas coleções:Repositório Institucional da Universidade Federal de Lavras (RIUFLA)

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