beta-Cyclodextrin/Isopentyl Caffeate Inclusion Complex: Synthesis, Characterization and Antileishmanial Activity
authors 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
nationality International
journal MOLECULES
author keywords isopentyl caffeate; beta-cyclodextrin; inclusion complex; leishmania
keywords ACID PHENETHYL ESTER; PHYSICOCHEMICAL PROPERTIES; ESSENTIAL OIL; NANOPARTICLES; OPTIMIZATION; AGENTS; ALPHA; MODEL
abstract 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.
publisher MDPI
isbn 1420-3049
year published 2020
volume 25
issue 18
digital object identifier (doi) 10.3390/molecules25184181
web of science category Biochemistry & Molecular Biology; Chemistry, Multidisciplinary
subject category Biochemistry & Molecular Biology; Chemistry
unique article identifier WOS:000580745500001
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journal analysis (jcr 2019):
journal impact factor 3.267
5 year journal impact factor 3.589
category normalized journal impact factor percentile 56.714
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