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Inclusion Complex of 4-Hydroxycoumarin with Cyclodextrins and Its Characterization in Aqueous Solution

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Abstract

The physicochemical properties of 4-hydroxy-7-methoxy-3-phenyl-2H-chromen-2-one (4HC) and β-cyclodextrins (CDs) inclusion complexes were investigated. The phase solubility profile of 4HC with β-cyclodextrin derivatives was classified as AL-type. Stability constants for complexes with 1:1 molar ratios were calculated from the phase solubility diagrams and indicate the following trend: DMβCD>HPβCD>βCD. The highest value of the binding constant was for 4HC-DMβCD; the binding association constant (K a) for this complex was determined at different temperatures and the thermodynamic data indicate that 4HC-DMβCD association is mainly an entropically driven process. 1H NMR and ROESY were carried out, revealing that 4HC is embedded in the apolar cavity of DMβCD with the 4OH group buried in the cyclodextrin cavity with the phenyl group outside, near the primary rim. These results are in agreement with ORACFL values; the decrease in the antioxidant activity of 4HC-DMβCD is explained by the effective protection of the hydroxyl group due to complexation.

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Acknowledgements

Our thanks are to Fondecyt 11080038 and to CEPEDEQ from Chemical and Pharmaceutical Science Faculty of University of Chile for the use of NMR.

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Authors and Affiliations

  1. Departamento Química Inorgánica y Analítica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Santiago, Chile

    Christian Folch-Cano & Claudio Olea-Azar

  2. Departamento de Farmacia y Tecnología Farmacéutica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782, Santiago de Compostela, Spain

    Eduardo Sobarzo-Sánchez, Carmen Alvarez-Lorenzo, Angel Concheiro & Francisco Otero

  3. Departamento Química Orgánica y Fisicoquímica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Santiago, Chile

    Carolina Jullian

Authors
  1. Christian Folch-Cano
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  2. Claudio Olea-Azar
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  3. Eduardo Sobarzo-Sánchez
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  4. Carmen Alvarez-Lorenzo
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  5. Angel Concheiro
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  7. Carolina Jullian
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Correspondence to Carolina Jullian.

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Folch-Cano, C., Olea-Azar, C., Sobarzo-Sánchez, E. et al. Inclusion Complex of 4-Hydroxycoumarin with Cyclodextrins and Its Characterization in Aqueous Solution. J Solution Chem 40, 1835–1846 (2011). https://doi.org/10.1007/s10953-011-9760-9

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  • DOI: https://doi.org/10.1007/s10953-011-9760-9

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