化学
氢键
疏水效应
分子
环糊精
组合化学
计算化学
芳香性
溶解度
有机化学
作者
Koleta Hemine,Anna Skwierawska,Cyprian Kleist,Michał Olewniczak,Katarzyna Szwarc-Karabyka,Dariusz Wyrzykowski,Anna Mieszkowska,Jarosław Chojnacki,Jacek Czub,Łukasz Nierzwicki
标识
DOI:10.1016/j.carbpol.2020.116957
摘要
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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