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Host–Guest Interaction Study of Resveratrol With Natural and Modified Cyclodextrins

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Abstract

The aim of this work is to increase the stability and water solubility of resveratrol by complexation with different cyclodextrins. Furthermore, physical–chemical properties of each inclusion compound were investigated. Complexes of resveratrol with cyclodextrins both native (α, β, γ) and modified (2-hydroxypropyl-β-cyclodextrin, dimethyl-β-cyclodextrin) were obtained by using the suspension method. An inclusion complex with β-cyclodextrin was also prepared by using the microwave. Solid state characterization of the products was carried out using Fourier transform infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC), X-ray diffraction (DRX); solution studies were performed by UV–Vis spectrophotometry and 1H-NMR spectroscopy. Phase solubility profiles with all cyclodextrins employed were classified as AN type, indicating the formation of 1:1 stoichiometric inclusion complexes. Stability constants (K c) from the phase solubility diagrams were calculated. Stability studies in the solid state and in solution were performed; the photodegradation by UV–Vis spectrophotometry was monitored. The isomerization rate trans to cis, in ethanol solution, decreased with inclusion. The dissolution studies revealed that resveratrol dissolution rate was improved by the formation of inclusion complexes.

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Acknowledgements

We are indebted to our Professor Riccardo Stradi (Istituto di Chimica Organica “A.Marchesini”, Università degli Studi di Milano, Facoltà di Farmacia) for the helpful suggestions.

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Authors and Affiliations

  1. Istituto di Chimica Organica “A. Marchesini”, Facoltà di Farmacia, Università di Milano, Via Venezian 21, 20133, Milano, Italy

    Vittorio Bertacche, Natascia Lorenzi, Donatella Nava & Elena Pini

  2. Dipartimento Farmaco Chimico Tecnologico, Università di Cagliari, Via Ospedale 72, 09124, Cagliari, Italy

    Chiara Sinico

Authors
  1. Vittorio Bertacche
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  2. Natascia Lorenzi
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  3. Donatella Nava
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  4. Elena Pini
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  5. Chiara Sinico
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Correspondence to Elena Pini.

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Bertacche, V., Lorenzi, N., Nava, D. et al. Host–Guest Interaction Study of Resveratrol With Natural and Modified Cyclodextrins. J Incl Phenom Macrocycl Chem 55, 279–287 (2006). https://doi.org/10.1007/s10847-006-9047-8

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  • DOI: https://doi.org/10.1007/s10847-006-9047-8

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