title: Molecular Modeling and Physicochemical Properties of Supramolecular Complexes of Limonene with α- and β-Cyclodextrins.
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.
authors.affiliation: Department of Pharmacy, Federal University of Sergipe, São Cristóvão, Sergipe, Brazil. paula.dp.menezes@gmail.com.
authors.forename: Paula
authors.initials: P
authors.lastname: Dos Passos Menezes
authors.affiliation: Department of Pharmacy, Federal University of Sergipe, São Cristóvão, Sergipe, Brazil.
authors.forename: Polliana Barbosa Pereira
authors.initials: PB
authors.lastname: Dos Santos
authors.affiliation: Department of Pharmacy, Federal University of Sergipe, São Cristóvão, Sergipe, Brazil.
authors.forename: Grace Anne Azevedo
authors.initials: GA
authors.lastname: Dória
authors.affiliation: Department of Pharmacy, Federal University of Sergipe, São Cristóvão, Sergipe, Brazil.
authors.forename: Bruna Maria Hipólito
authors.initials: BM
authors.lastname: de Sousa
authors.affiliation: Department of Pharmacy, Federal University of Sergipe, São Cristóvão, Sergipe, Brazil.
authors.forename: Mairim Russo
authors.initials: MR
authors.lastname: Serafini
authors.affiliation: Department of Pharmacy, Federal University of Sergipe, São Cristóvão, Sergipe, Brazil.
authors.forename: Paula Santos
authors.initials: PS
authors.lastname: Nunes
authors.affiliation: Department of Physiology, Federal University of Sergipe, São Cristóvão, Sergipe, Brazil.
authors.forename: Lucindo José
authors.initials: LJ
authors.lastname: Quintans-Júnior
authors.affiliation: Department of Chemistry, Federal University of Sergipe, São Cristóvão, Sergipe, Brazil.
authors.forename: Iara Lisboa
authors.initials: IL
authors.lastname: de Matos
authors.affiliation: Department of Chemistry, Federal University of Sergipe, São Cristóvão, Sergipe, Brazil.
authors.forename: Péricles Barreto
authors.initials: PB
authors.lastname: Alves
authors.affiliation: Gonçalo Moniz Research Center, Oswaldo Cruz Foundation, Salvador, Bahia, Brazil.
authors.forename: Daniel Pereira
authors.initials: DP
authors.lastname: Bezerra
authors.affiliation: Laboratory of Synthesis and Vectorization of Molecules, State University of Paraíba, Campina Grande, Paraíba, Brazil.
authors.forename: Francisco Jaime Bezerra
authors.initials: FJ
authors.lastname: Mendonça Júnior
authors.affiliation: Department of Chemical Engineering, Federal University of Sergipe, São Cristóvão, Sergipe, Brazil.
authors.forename: Gabriel Francisco
authors.initials: GF
authors.lastname: da Silva
authors.affiliation: Laboratory of Nuclear Magnetic Resonance, Institute of Chemistry and Biotechnology - Federal University of Alagoas, Maceió, Brazil.
authors.forename: Thiago Mendonça
authors.initials: TM
authors.lastname: de Aquino
authors.affiliation: Laboratory of Nuclear Magnetic Resonance, Institute of Chemistry and Biotechnology - Federal University of Alagoas, Maceió, Brazil.
authors.forename: Edson
authors.initials: E
authors.lastname: de Souza Bento
authors.affiliation: Federal University of Paraíba, João Pessoa, Paraíba, Brazil.
authors.forename: Marcus Tullius
authors.initials: MT
authors.lastname: Scotti
authors.affiliation: Federal University of Paraíba, João Pessoa, Paraíba, Brazil.
authors.forename: Luciana
authors.initials: L
authors.lastname: Scotti
authors.affiliation: Department of Pharmacy, Federal University of Sergipe, São Cristóvão, Sergipe, Brazil. adriasa2001@yahoo.com.br.
authors.forename: Adriano Antunes
authors.initials: AA
authors.lastname: de Souza Araujo
mesh_terms: D002849:Chromatography, Gas / Q000379:methods; D053138:Cyclohexenes / Q000737:chemistry*; D000077222:Limonene; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013058:Mass Spectrometry / Q000379:methods; D008958:Models, Molecular; D012995:Solubility; D013055:Spectrophotometry, Infrared / Q000379:methods; D013729:Terpenes / Q000737:chemistry*; D013818:Thermogravimetry / Q000379:methods; D014961:X-Ray Diffraction / Q000379:methods; D047391:alpha-Cyclodextrins / Q000737:chemistry*; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D053138:Cyclohexenes; D013729:Terpenes; D047391:alpha-Cyclodextrins; D047392:beta-Cyclodextrins; D000077222:Limonene; C032613:alpha-cyclodextrin
keywords: cyclodextrin; inclusion complex; limonene; monoterpene