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Thermodynamics of complex formation between hydroxypropyl-β-cyclodextrin and quercetin in water–ethanol solvents at T = 298.15 K

  • Tatiana UsachevaEmail author
  • Dzhovidon Kabirov
  • Diana Beregova
  • George Gamov
  • Valentin Sharnin
  • Marco Biondi
  • Laura Mayol
  • Federica D’Aria
  • Concetta Giancola
Article
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Abstract

Quercetin (QCT) is a flavonoid possessing many activities, such as neuro-/cardioprotective, anti-inflammatory and anticancer, but its pharmacological application is severely curtailed by its low water solubility and in vivo bioavailability. The formation of a QCT–hydroxypropyl-β-cyclodextrin (HPβCD) host–guest complex is promising to improve QCT therapeutic potential. Therefore, here the heat effects of HPβCD solutions with QCT solutions in water–ethanol solvents at different concentrations were studied by calorimetric titration, and the stability of molecular complexes was assessed by UV–Vis spectrophotometry. Calorimetric titrations revealed the formation of a QCT/HPβCD host–guest complex with a stoichiometric ratio of 1:1 in X(EtOH) = 0.00, 0.05 and 0.10 molar fractions of solvents at pH = 7.0 and pH = 8.1. Thermodynamic parameters of the complex formation reaction (lgK; ΔrH; TΔrS) were obtained in these experimental conditions. Differently, no complex formation was noticed in water–ethanol mixed solvent when ethanol volume fraction exceeded 0.2 at neutral and alkaline pH, as well as a volume fraction higher than 0.1 at acidic pH. Furthermore, the results of differential scanning calorimetry tests run on dried HPβCD after dissolution in hydroalcoholic solutions indicated that ethanol and water compete for the complexation within the hydrophobic cavity of HPβCD. This explains the decreased QCT complexation efficacy in the presence of ethanol beyond 0.1 or 0.2 volume fraction.

Keywords

Quercetin Hydroxypropyl-β-cyclodextrin Isothermal calorimetry UV–Vis spectrophotometry Inclusion complexation Water–ethanol solvents 

Notes

Acknowledgements

The calorimetric measurements presented in this work were carried out at the Institute of Thermodynamics and Kinetics of Chemical Processes of the Ivanovo State University of Chemistry and Technology (ISUCT) using the equipment of the Center for Collective Use of ISUCT. The study was carried out under grant of Council on grants of the President of the Russian Federation (Project 14.Z56.18.877-MK). The authors thank the University of Naples Federico II for the financial support of their collaboration contributed to the preparation of this paper.

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Copyright information

© Akadémiai Kiadó, Budapest, Hungary 2019

Authors and Affiliations

  • Tatiana Usacheva
    • 1
    Email author
  • Dzhovidon Kabirov
    • 1
  • Diana Beregova
    • 1
  • George Gamov
    • 1
  • Valentin Sharnin
    • 1
  • Marco Biondi
    • 2
    • 3
  • Laura Mayol
    • 2
    • 3
  • Federica D’Aria
    • 2
  • Concetta Giancola
    • 2
  1. 1.Department of General Chemical Technology, Faculty of Inorganic Chemistry and TechnologyIvanovo State University of Chemistry and TechnologyIvanovoRussian Federation
  2. 2.Department of PharmacyUniversity of Naples Federico IINaplesItaly
  3. 3.Interdisciplinary Research Centre on Biomaterials – CRIBUniversità di Napoli Federico IINaplesItaly

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