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Host–guest system of 4-nerolidylcatechol in 2-hydroxypropyl-β-cyclodextrin: preparation, characterization and molecular modeling

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Abstract

The interaction of 4-nerolidylcatechol (4-NRC), a potent antioxidant agent, and 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) was investigated by the solubility method using Fourier transform infrared (FTIR) methods in addition to UV–Vis, 1H-nuclear magnetic resonance (NMR) spectroscopy and molecular modeling. The inclusion complexes were prepared using grinding, kneading and freeze-drying methods. According to phase solubility studies in water a BS-type diagram was found, displaying a stoichiometry complexation of 2:1 (drug:host) and stability constant of 6494 ± 837 M−1. Stoichiometry was established by the UV spectrophotometer using Job’s plot method and, also confirmed by molecular modeling. Data from 1H-NMR, and FTIR, experiments also provided formation evidence of an inclusion complex between 4-NRC and HP-β-CD. 4-NRC complexation indeed led to higher drug solubility and stability which could probably be useful to improve its biological properties and make it available to oral administration and topical formulations.

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Acknowledgments

This work was partly supported by a grant from CNPq and SECTEC-GO. The authors acknowledge Dr. Massayoshi Yoshida and Dr. Luiz Carlos Roque for the NMR 500 MHz data acquisition. We are especially grateful to Prof. Harry Pearson for English corrections on the manuscript.

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Authors and Affiliations

  1. Laboratório de Biofarmácia e Farmacocinética, Faculdade de Farmácia, Universidade Federal de Goiás, Praça Universitária, 1166. Setor Universitário, 74605-220, Goiânia, GO, Brazil

    Líllian Amélia Soares, Ana Flávia Vasconcelos Borges Leal, Eric de Sousa Gil, Luiz Carlos da Cunha & Kênnia Rocha Rezende

  2. Departamento de Engenharia Ambiental, Universidade Estadual Paulista, Sorocaba, SP, Brazil

    Leonardo Fernandes Fraceto

  3. Instituto de Química, Universidade de Brasília, Brasília, DF, Brazil

    Elaine Rose Maia & Inês Sabioni Resck

  4. Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, São Paulo, SP, Brazil

    Massuo Jorge Kato

  5. Instituto de Quimica, Universidade Federal de Goiás, Goiânia, GO, Brazil

    Aparecido Ribeiro de Sousa

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  1. Líllian Amélia Soares
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Correspondence to Kênnia Rocha Rezende.

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Soares, L.A., Leal, A.F.V.B., Fraceto, L.F. et al. Host–guest system of 4-nerolidylcatechol in 2-hydroxypropyl-β-cyclodextrin: preparation, characterization and molecular modeling. J Incl Phenom Macrocycl Chem 64, 23–35 (2009). https://doi.org/10.1007/s10847-009-9532-y

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