Publications Repository - Gdańsk University of Technology

It is widely believed that the hydrophobic effect governs the binding of guest molecules to cyclodextrins (CDs). However, it is also known that high hydrophobicity of guest molecules does not always translate to the formation of stable inclusion complexes with CDs. Indeed, a plethora of other factors can play a role in the efficiency of guest–CD interactions, rendering structure-based prediction of the complexation efficiency with CDs a non trivial task. In this combined experimental and computational study, we examine the major structural factors governing complexation efficiency of polycyclic aromatic drug-like compounds with natural CDs, using as an example iminostilbene and its N-substituted derivatives. We find that purely hydrophobic IS derivatives show negligible complexation efficiency with CDs and only IS with hydrophilic substituents form stable inclusion complexes in water. We show that the balance between the guest solubility and its affinity to CDs is critical for the effective formation of inclusion complexes. Finally, our results demonstrate that guest–host hydrogen bonds facilitate the formation of crystalline inclusion complexes with CDs.

Authors

• dr inż. Koleta Hemine link open in new tab ,
• dr hab. inż. Anna Skwierawska link open in new tab ,
• mgr Cyprian Kleist link open in new tab ,
• Michał Olewniczak link open in new tab ,
• dr inż. Katarzyna Szwarc-Karabyka link open in new tab ,
• Dariusz Wyrzykowski,
• Anna Mieszkowska link open in new tab ,
• prof. dr hab. inż. Jarosław Chojnacki link open in new tab ,
• prof. dr hab. inż. Jacek Czub link open in new tab ,
• dr inż. Łukasz Nierzwicki link open in new tab