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Ionic resorcinarenes as drug solubilization agents in water.
Frank Boateng Osei1, Kwaku Twum1, Barbara Manfredi2
1Oakland University, Department of Chemistry 146 Library Drive Rochester MI 48309-4479 USA beyeh@oakland.edu.
RSC Advances
|October 29, 2024
Summary
Hydrophilic resorcinarenes significantly enhance the aqueous solubility of hydrophobic drugs like isoniazid, caffeine, and griseofulvin. These resorcinarene-drug complexes show no cytotoxicity, indicating potential as drug delivery aids.
Area of Science:
- Supramolecular Chemistry
- Materials Science
- Pharmaceutical Sciences
Background:
- Resorcinarenes are known for host-guest complexation but are underexplored for pharmaceutical applications.
- Improving the aqueous solubility of hydrophobic drugs is crucial for effective drug delivery.
Purpose of the Study:
- To investigate the potential of hydrophilic resorcinarenes as solubilizing agents for hydrophobic drugs.
- To evaluate the impact of resorcinarenes on the aqueous solubility and delivery of isoniazid, caffeine, and griseofulvin.
Main Methods:
- Dynamic light scattering (DLS) to assess particle size changes.
- Isothermal titration calorimetry (ITC) to quantify binding affinities.
- Nuclear magnetic resonance (NMR) spectroscopy (¹H NMR) to confirm molecular interactions.
Main Results:
- Resorcinarene-drug mixtures exhibited enhanced solubility and clarity compared to pure drug solutions.
- DLS showed a shift in drug particle sizes into the resorcinarene host range.
- ¹H NMR confirmed interactions with chemical shift changes from -0.20 to 0.81 ppm.
- ITC revealed binding affinities between 0.54 and 211 mM.
- Cytotoxicity studies on HEK-293 cells indicated no adverse effects up to 200 μM.
Conclusions:
- Hydrophilic resorcinarenes effectively enhance the aqueous solubility of hydrophobic drugs.
- Resorcinarene-drug complexes demonstrate favorable binding interactions and lack cytotoxicity.
- Resorcinarene macrocycles show promise as novel drug solubilizers for pharmaceutical applications.
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