beta-Cyclodextrin/Isopentyl Caffeate Inclusion Complex: Synthesis, Characterization and Antileishmanial Activity


Isopentyl caffeate (ICaf) is a bioactive ester widely distributed in nature. Our patented work has shown promising results of this molecule against Leishmania. However, ICaf shows poor solubility, which limits its usage in clinical settings. In this work, we have proposed the development of an inclusion complex of ICaf in beta-cyclodextrin (beta-CD), with the aim to improve the drug solubility, and thus, its bioavailability. The inclusion complex (ICaf:beta-CD) was developed applying three distinct methods, i.e., physical mixture (PM), kneading (KN) or co-evaporation (CO) in different molar proportions (0.25:1, 1:1 and 2:1). Characterization of the complexes was carried out by thermal analysis, Fourier-transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM) and molecular docking. The ICaf:beta-CD complex in a molar ratio of 1:1 obtained by CO showed the best complexation and, therefore, was selected for further analysis. Solubility assay showed a marked improvement in the ICaf:beta-CD (CO, 1:1) solubility profile when compared to the pure ICaf compound. Cell proliferation assay using ICaf:beta-CD complex showed an IC(50)of 3.8 and 2.7 mu g/mL againstL. amazonesisandL. chagasipromastigotes, respectively. These results demonstrate the great potential of the inclusion complex to improve the treatment options for visceral and cutaneous leishmaniases.



subject category

Biochemistry & Molecular Biology; Chemistry


Marques, CSF; Barreto, NS; de Oliveira, SSC; Santos, ALS; Branquinha, MH; de Sousa, DP; Castro, M; Andrade, LN; Pereira, MM; da Silva, CE; Chaud, MV; Jain, S; Fricks, AT; Souto, EB; Severino, P

our authors


This research was funded by Banco do Nordeste (grant FUNDECI/2016.0015), Coordenacao Aperfeicoamento de Pessoal de Nivel Superior (CAPES) and Fundacao de Amparo a Pesquisa do Estado de Sergipe (FAPITEC) (PROCESSO: 88887.159533/2017-00 extracao, encapsulacao e caracterizacao de bioativos para o interesse biotecnologico). Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq 301964/2019-0 Chamada 06/2019, and Chamada CNPq no 01/2019) and from the Portuguese Science and Technology Foundation (FCT) project UIDB/04469/2020 (strategic fund).

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