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Molecular Modeling and Physicochemical Properties of Supramolecular Complexes of Limonene with α- and β-Cyclodextrins

2016; Springer Science+Business Media; Volume: 18; Issue: 1 Linguagem: Inglês

10.1208/s12249-016-0516-0

1530-9932

Paula dos Passos Menezes, Polliana Barbosa Pereira dos Santos, Grace Anne Azevedo Dória, Bruna Maria Hipólito de Sousa, Mairim Russo Serafini, Paula Santos Nunes, Lucindo José Quintans‐Júnior, Iara Lisboa de Matos, Péricles Barreto Alves, Daniel P. Bezerra, Francisco Jaime Bezerra Mendonça, Gabriel Francisco da Silva, Thiago Mendonça de Aquino, Edson de Souza Bento, Luciana Scotti, Luciana Scotti, Adriano Antunes de Souza Araújo,

Analytical Methods in Pharmaceuticals

This study evaluated three different methods for the formation of an inclusion complex between alpha- and beta-cyclodextrin (α- and β-CD) and limonene (LIM) with the goal of improving the physicochemical properties of limonene. The study samples were prepared through physical mixing (PM), paste complexation (PC), and slurry complexation (SC) methods in the molar ratio of 1:1 (cyclodextrin:limonene). The complexes prepared were evaluated with thermogravimetry/derivate thermogravimetry, infrared spectroscopy, X-ray diffraction, complexation efficiency through gas chromatography/mass spectrometry analyses, molecular modeling, and nuclear magnetic resonance. The results showed that the physical mixing procedure did not produce complexation, but the paste and slurry methods produced inclusion complexes, which demonstrated interactions outside of the cavity of the CDs. However, the paste obtained with β-cyclodextrin did not demonstrate complexation in the gas chromatographic technique because, after extraction, most of the limonene was either surface-adsorbed by β-cyclodextrin or volatilized during the procedure. We conclude that paste complexation and slurry complexation are effective and economic methods to improve the physicochemical character of limonene and could have important applications in pharmacological activities in terms of an increase in solubility.