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Transport Properties of Ibuprofen Encapsulated in Cyclodextrin Nanosponge Hydrogels: A Proton HR-MAS NMR Spectroscopy Study
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A thermodynamic study of the cyclodextrin-UC781 inclusion complex using a HPLC method.

Haitao Yang1, Michael A Parniak2, Sharon L Hillier3

  • 1Department of Pharmaceutical Sciences, School of Pharmacy, University of Pittsburgh, Pittsburgh, PA, USA.

Journal of Inclusion Phenomena and Macrocyclic Chemistry
|June 23, 2015
PubMed
Summary

This study investigated how cyclodextrins (CDs) interact with UC781, a potential HIV microbicide. Methyl-β-cyclodextrin showed the highest inclusion capacity, indicating an enthalpy-driven complexation process.

Keywords:
EnthalpyHPLCNon-nucleoside reverse transcriptase inhibitor (NNRTI)ThermodynamicsUC781β-cyclodextrin inclusion complex

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Area of Science:

  • Pharmaceutical Sciences
  • Physical Chemistry
  • Drug Delivery

Background:

  • UC781 is a potent HIV-1 non-nucleoside reverse transcriptase inhibitor.
  • Its extreme hydrophobicity and poor water solubility present challenges for topical vaginal microbicide development.
  • Cyclodextrins (CDs) are known to improve the solubility and bioavailability of hydrophobic drugs.

Purpose of the Study:

  • To investigate the thermodynamic behavior of UC781 complexation with three different cyclodextrins: β-cyclodextrin (βCD), hydroxypropyl-β-cyclodextrin (HPβCD), and methyl-β-cyclodextrin (MβCD).
  • To evaluate the influence of cyclodextrins on the solubility and hydrophobicity of UC781.
  • To determine the driving forces behind the UC781-CD interaction.

Main Methods:

  • Reversed-phase High-Performance Liquid Chromatography (HPLC) method.
  • Utilized a mobile phase of acetonitrile: H2O (30:70) with varying cyclodextrin concentrations.
  • Measured retention times at different temperatures to assess inclusion processes and thermodynamic parameters.

Main Results:

  • The inclusion capacity of the cyclodextrins followed the order: MβCD > βCD > HPβCD.
  • An enthalpy-entropy compensation effect was observed.
  • The complexation of UC781 with βCDs was determined to be an enthalpy-driven process, with ΔH changes exceeding ΔS changes.

Conclusions:

  • The choice of cyclodextrin modification significantly influences the inclusion process and the complexation of UC781.
  • Understanding these thermodynamic interactions is crucial for optimizing UC781 formulation as a topical microbicide.
  • MβCD demonstrates the greatest potential for enhancing UC781's properties among the tested cyclodextrins.