Investigating the differences in β-Cyclodextrin derivatives / Hyperoside inclusion complexes: Dissolution properties,...

Area of Science:

• Supramolecular Chemistry
• Materials Science
• Pharmacology

Background:

• Understanding structure-activity relationships in cyclodextrin inclusion complexes is vital for drug design.
• Hyperoside (HYP) is a flavonoid with potential therapeutic benefits but limited solubility and bioavailability.
• Cyclodextrins (CDs) are widely used to improve the physicochemical properties of poorly soluble drugs.

Purpose of the Study:

• To investigate the encapsulation of hyperoside (HYP) using native β-cyclodextrin (β-CD), dimethyl-β-cyclodextrin (DM-β-CD), and hydroxypropyl-β-cyclodextrin (HP-β-CD).
• To evaluate the impact of different β-CD derivatives on HYP's dissolution rate, solubility, and antioxidant activity.
• To elucidate the molecular interactions governing the stability and properties of these inclusion complexes.

Main Methods:

• Freeze-drying method for preparing HYP/β-CD inclusion complexes.
• Molecular docking and molecular dynamics (MD) simulations to predict binding energies and analyze interactions.
• Dissolution rate testing, DPPH and ABTS+ radical scavenging assays to assess antioxidant activity.
• Differential scanning calorimetry (DSC) to evaluate thermal stability.

Main Results:

• DM-β-CD/HYP complexes showed the highest dissolution rate (93.63%), significantly improving upon HYP alone (60.34%).
• DM-β-CD/HYP complexes exhibited enhanced free radical scavenging activity against DPPH (80.67%) and ABTS+ (46.32%).
• Molecular simulations revealed hydrophobic interactions are crucial for solubility enhancement, while hydrogen bonding ensures complex stability, especially at higher temperatures.

Conclusions:

• DM-β-CD is a promising carrier for improving hyperoside's solubility, bioavailability, and antioxidant efficacy.
• Hydrophobic interactions and hydrogen bonding play critical roles in the formation, stability, and performance of HYP/β-CD inclusion complexes.
• The study provides insights into rational design strategies for developing effective cyclodextrin-based drug delivery systems.