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Cyclodextrin solubilization in hydrated reline: Resolving the unique stabilization mechanism in a deep eutectic
Ilan Shumilin1, Daniel Harries1
1The Fritz Haber Research Center, and The Harvey M. Krueger Family Center for Nanoscience and Nanotechnology, Edmond J. Safra Campus, Institute of Chemistry, The Hebrew University, Jerusalem 9190401, Israel.
The Journal of Chemical Physics
|July 9, 2021
Summary
Deep eutectic solvents (DESs), specifically reline, significantly enhance beta-cyclodextrin solubility. Urea inclusion in the cyclodextrin cavity and choline chloride
Area of Science:
- Supramolecular Chemistry
- Physical Chemistry
- Materials Science
Background:
- Cyclodextrins are crucial for solubilizing hydrophobic compounds in pharmaceuticals.
- Poor water solubility of common cyclodextrins like beta-cyclodextrin limits their applications.
- Deep eutectic solvents (DESs) offer unique properties as alternative solvents.
Purpose of the Study:
- To investigate the solvation mechanism of beta-cyclodextrin in the DES reline (choline chloride and urea).
- To understand how reline constituents enhance beta-cyclodextrin solubility compared to water or dry reline.
- To elucidate the role of urea and choline chloride in beta-cyclodextrin solubilization.
Main Methods:
- Combination of experimental techniques and molecular simulations.
- Analysis of beta-cyclodextrin solvation in hydrated and dry reline solutions.
- Investigation of constituent interactions within the DES and with beta-cyclodextrin.
Main Results:
- Beta-cyclodextrin solubility is significantly enhanced in hydrated reline, primarily due to urea inclusion.
- Choline chloride further boosts solubility by increasing urea's solubility limit and promoting its accumulation near beta-cyclodextrin.
- In dry DES, solvation shifts to a quasi-single component mechanism without specific constituent accumulation.
Conclusions:
- Hydrated reline is a superior solvent for beta-cyclodextrin compared to aqueous solutions.
- The synergistic effect of urea and choline chloride drives enhanced beta-cyclodextrin solubilization in DES.
- Understanding these solvation mechanisms is key to optimizing cyclodextrin applications in DES.
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