Please use this identifier to cite or link to this item: https://www.arca.fiocruz.br/handle/icict/17831
Title: Molecular modeling and physicochemical properties of supramolecular complexes of limonene with α- and β-Cyclodextrins
Authors: Menezes, Paula dos Passos
Santos, Polliana Barbosa Pereira dos
Dória, Grace Anne Azevedo
Sousa, Bruna Maria Hipólito de
Serafini, Mairim Russo
Nunes, Paula Santos
Quintans Júnior, Lucindo José
Matos, Iara Lisboa de
Alves, Péricles Barreto
Bezerra, Daniel Pereira
Mendonça Júnior, Francisco Jaime Bezerra
Silva, Gabriel Francisco da
Aquino, Thiago Mendonça de
Bento, Edson de Souza
Scotti, Marcus Tullius
Scotti, Luciana
Araujo, Adriano Antunes de Souza
Affilliation: Universidade Federal de Sergipe. Departamento de Farmácia. São Cristóvão, SE, Brasil.
Universidade Federal de Sergipe. Departamento de Farmácia. São Cristóvão, SE, Brasil.
Universidade Federal de Sergipe. Departamento de Farmácia. São Cristóvão, SE, Brasil.
Universidade Federal de Sergipe. Departamento de Farmácia. São Cristóvão, SE, Brasil.
Universidade Federal de Sergipe. Departamento de Farmácia. São Cristóvão, SE, Brasil.
Universidade Federal de Sergipe. Departamento de Farmácia. São Cristóvão, SE, Brasil.
Universidade Federal de Sergipe. Departamento de Fisiologia. São Cristóvão, SE, Brasil.
Universidade Federal de Sergipe. Departamento de Química. São Cristóvão, SE, Brasil.
Universidade Federal de Sergipe. Departamento de Química. São Cristóvão, SE, Brasil.
Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil.
Universidade Estadual da Paraíba. Laboratório de Síntese e Vectorização de Moléculas. Campina Grande, PB, Brasil.
Universidade Federal de Sergipe. Departamento de Engenharia Química. São Cristóvão, SE, Brasil.
Universidade Federal de Alagoas. Instituto de Química e Biotecnologia. Laboratório de Ressonância Magnética Nuclear. Maceió, AL, Brasil.
Universidade Federal da Paraíba. João Pessoa, PB, Brasil.
Universidade Federal da Paraíba. João Pessoa, PB, Brasil.
Universidade Federal de Sergipe. Departamento de Farmácia. São Cristóvão, SE, Brasil.
Abstract: 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.
Keywords: Cyclodextrin
Inclusion complex
Limonene
Monoterpene
keywords: Ciclodextrina
Complexo de inclusão
Limoneno
Monoterpeno
DeCS: Limoneno Hidroxilases
Issue Date: 2017
Publisher: AAPS
Citation: MENEZES, Paula dos Passos et al. Molecular modeling and physicochemical properties of supramolecular complexes of limonene with α- and β-Cyclodextrins. AAPS PharmSciTech, v. 18, n. 1, p. 49-57, 2017.
DOI: 10.1208/s12249-016-0516-0
ISSN: 1530-9932
Copyright: open access
Appears in Collections:IGM - Artigos de Periódicos

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