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Polymorphism in the 1/1 Pterostilbene/Picolinic Acid Cocrystal.
Rafael Barbas1, Mercè Font-Bardia2, Antonio Frontera3
1Unitat de Polimorfisme i Calorimetria, Centres Científics i Tecnològics, Universitat de Barcelona, Baldiri Reixac 10, 08028 Barcelona, Spain.
Crystal Growth & Design
|January 13, 2022
Summary
Two new crystal forms of pterostilbene/picolinic acid cocrystal reveal a novel hydrogen bond pattern. This discovery enhances understanding of cocrystal structures and their bioavailability for crystal engineering applications.
Area of Science:
- Crystal Engineering
- Supramolecular Chemistry
- Computational Chemistry
Background:
- Pterostilbene and picolinic acid are key compounds in pharmaceutical research.
- Cocrystals offer tunable physicochemical properties for drug delivery.
- Understanding cocrystal polymorphism is crucial for developing stable and effective formulations.
Purpose of the Study:
- To analyze the crystal structures of two new polymorphs of the pterostilbene/picolinic acid cocrystal.
- To investigate the energetic and electronic properties of the observed supramolecular synthons.
- To elucidate the factors contributing to the cocrystal's bioavailability and explore picolinic acid's role as a coformer.
Main Methods:
- Single-crystal X-ray diffraction for structural determination.
- Density Functional Theory (DFT) calculations for electronic structure analysis.
- Quantum Theory of Atoms in Molecules (QTAIM), Non-covalent Interaction (NCI) plotting, and Molecular Electrostatic Potential (MEP) mapping for characterizing interactions.
- Bader-Engels-Fukuda-Hale (BFDH) morphology calculations for bioavailability assessment.
Main Results:
- Two new polymorphs of the 1/1 pterostilbene/picolinic acid cocrystal were identified and structurally characterized.
- A novel R2(2)(10) synthon was observed in both polymorphs, with detailed energetic and electronic analyses provided.
- The exceptional bioavailability of the cocrystal was correlated with its BFDH morphology.
- Analysis of supramolecular synthons formed by neutral and zwitterionic picolinic acid was performed.
Conclusions:
- The study successfully characterized new polymorphs of a pterostilbene/picolinic acid cocrystal, revealing a novel synthon.
- Computational methods provided deep insights into the nature of intermolecular interactions and their influence on crystal structure.
- The findings contribute to the understanding of crystal engineering principles and the design of cocrystals with enhanced bioavailability, highlighting picolinic acid as a versatile coformer.
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