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Effect of chemical structure on complexation efficiency of aromatic drugs with cyclodextrins: The example of dibenzazepine derivatives
Abstract
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.
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Authors (10)
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Dariusz Wyrzykowski
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- Category:
- Articles
- Type:
- artykuły w czasopismach
- Published in:
-
CARBOHYDRATE POLYMERS
no. 250,
ISSN: 0144-8617 - Language:
- English
- Publication year:
- 2020
- Bibliographic description:
- Hemine K., Skwierawska A., Kleist C., Olewniczak M., Szwarc-Karabyka K., Wyrzykowski D., Mieszkowska A., Chojnacki J., Czub J., Nierzwicki Ł.: Effect of chemical structure on complexation efficiency of aromatic drugs with cyclodextrins: The example of dibenzazepine derivatives// CARBOHYDRATE POLYMERS -Vol. 250, (2020), s.116957-
- DOI:
- Digital Object Identifier (open in new tab) 10.1016/j.carbpol.2020.116957
- Verified by:
- Gdańsk University of Technology
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