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Docking and physico-chemical properties of α- and β-cyclodextrin complex containing isopulegol: a comparative study

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Abstract

Isopulegol (ISOP) is a monoterpenoid alcohol presented in the essential oils of several plants that possesses therapeutic properties The aim of this work was prepare samples with ISOP and α- and β-cyclodextrins (α- and β-CD) through three different methods: physical mixture, paste method (PC) and slurry complexation (SC). In order to evaluate the formation of inclusion complexes, the techniques of differential scanning calorimetry, thermogravimetry/derivative thermogravimetry, fourier transform infrared spectroscopy, X-ray diffractometry (XRD), gas chromatography–mass spectrometry analyses (GC/MS), docking, nuclear magnetic resonance and scanning electron microscopy were considered. The analyses of the α-CD or β-CD/ISOP revealed the formation of a complex mainly through the PC and SC methods for α-CD and β-CD, respectively. XRD diffraction characteristics presented formation of a trend to new solid phase, which suggested the formation of inclusion complexes. The GC/MS demonstrated that the PC method was the best one to form complexation with α-CD (48.8 %). Concerning β-CD, the SC method exhibited the strongest complexation (68.3 %). Furthermore, the molecular theoretical docking study demonstrated that α-CD/ISOP inclusion complex formed a more stable complex than did the β-CD/ISOP inclusion complex.

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Acknowledgments

The authors are grateful to CAPES, CNPq, FINEP and FAPITEC/SE for the financial support and fellowships. We thank M. L. V. Moreno, C. P. Figueira and Prof. A. L. Rangel for the images of SEM made in the Gonçalo Moniz Research Center, at the Oswaldo Cruz Foundation.

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Authors and Affiliations

  1. Departamento de Farmácia, Universidade Federal de Sergipe, São Cristóvão, Sergipe, Brazil

    Paula dos Passos Menezes, Grace Anne Azevedo Dória, Adriano Antunes de Souza Araújo, Bruna Maria Hipólito Sousa & Mairim Russo Serafini

  2. Departamento de Fisiologia, Universidade Federal de Sergipe, São Cristóvão, Sergipe, Brazil

    Lucindo José Quintans-Júnior

  3. Departamento de Química, Universidade Federal de Sergipe, São Cristóvão, Sergipe, Brazil

    Rafaely Nascimento Lima & Péricles Barreto Alves

  4. Departamento de Mineralogia e Geotectônica, Universidade de São Paulo, São Paulo, Brazil

    Flávio Machado Souza Carvalho

  5. Centro de Pesquisa Gonçalo Moniz, Fundação Oswaldo Cruz, Salvador, Bahia, Brazil

    Daniel Pereira Bezerra

  6. Laboratório de Síntese e Vetorização de Moléculas, Universidade Estadual da Paraíba, Campina Grande, Paraíba, Brazil

    Francisco Jaime Bezerra Mendonça-Júnior

  7. Universidade Federal da Paraíba, Campina Grande, Paraíba, Brazil

    Luciana Scotti

  8. Departamento de Engenharia e Ambiente, Universidade Federal da Paraíba, Campina Grande, Paraíba, Brazil

    Marcus Tullius Scotti

  9. Departamento de Engenharia Química, Universidade Federal de Sergipe, São Cristóvão, Sergipe, Brazil

    Gabriel Francisco da Silva

  10. Laboratório de Ressonância Magnética Nuclear, Universidade Federal de Alagoas, Maceió, Alagoas, Brazil

    Thiago Mendonça de Aquino & Adilson Rodrigues Sabino

  11. Departamento de Farmácia, Universidade Federal do Rio Grande do Norte, Natal, Rio Grande do Norte, Brazil

    Eryvaldo Socrates Tabosa do Egito

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  1. Paula dos Passos Menezes
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dos Passos Menezes, P., Dória, G.A.A., de Souza Araújo, A.A. et al. Docking and physico-chemical properties of α- and β-cyclodextrin complex containing isopulegol: a comparative study. J Incl Phenom Macrocycl Chem 85, 341–354 (2016). https://doi.org/10.1007/s10847-016-0633-0

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