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Native Cyclodextrins as Complexation Agents for Pterostilbene: Complex Preparation and Characterization in Solution

Laura Catenacci¹, Alexios I Vicatos², Milena Sorrenti¹

¹Department of Drug Sciences, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy.

|January 21, 2022

Summary

Pterostilbene (PTB) complexation with cyclodextrins (CDs) was studied to enhance its low aqueous solubility. Beta- and gamma-cyclodextrins effectively complexed PTB, significantly improving its dissolution rate for potential therapeutic applications.

Keywords:

X-ray diffraction complexation cyclodextrin pterostilbene thermal analysis

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Published on: August 12, 2019

Area of Science:

Pharmaceutical Sciences
Materials Science
Supramolecular Chemistry

Background:

Pterostilbene (PTB), a natural stilbene found in blueberries, exhibits promising antioxidant, anti-inflammatory, and anticarcinogenic properties.
Therapeutic application of PTB is limited by its poor aqueous solubility, necessitating strategies to enhance its bioavailability.

Purpose of the Study:

To investigate the feasibility of complexing pterostilbene (PTB) with native cyclodextrins (CDs) to improve its aqueous solubility.
To characterize the inclusion complexes formed between PTB and α-, β-, and γ-CDs using various analytical techniques.

Main Methods:

Complexation of PTB with α-, β-, and γ-CDs using kneading and co-precipitation methods.
Characterization of solid complexes using DSC, TGA/DSC, FT-IR, ¹H-NMR, and single-crystal X-ray diffraction (XRD).
Phase-solubility studies to determine complex stoichiometry and association constants (K_1:1).

Main Results:

Complexation was minimal with α-CD, but significant interactions were observed with β-CD and γ-CD, confirmed by thermal and spectroscopic analyses.
Single-crystal XRD elucidated the inclusion mode of PTB within the β-CD cavity for the first time.
Phase-solubility studies revealed A_L-type profiles for α- and β-CD and a B_S profile for γ-CD, with K_1:1 values of 1144, 4950, and 133 M^-1, respectively.
Dissolution rates of PTB were significantly enhanced, with complete dissolution achieved in 40 min (β-CD) and 20 min (γ-CD) via kneading and co-precipitation.

Conclusions:

Beta-cyclodextrin and gamma-cyclodextrin are effective complexing agents for pterostilbene, significantly enhancing its aqueous solubility and dissolution rate.
The study provides a structural basis for PTB-CD complexation and demonstrates a viable strategy for improving PTB's pharmaceutical formulation.