Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 275, 760 01 Zlín, Czech Republic.
CEITEC - Central European Institute of Technology, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic.
J Org Chem. 2021 Mar 19;86(6):4483-4496. doi: 10.1021/acs.joc.0c02917. Epub 2021 Mar 1.
Multitopic supramolecular guests with finely tuned affinities toward widely explored cucurbit[]urils (CBs) and cyclodextrins (CDs) have been recently designed and tested as functional components of advanced supramolecular systems. We employed various spacers between the adamantane cage and a cationic moiety as a tool for tuning the binding strength toward CB7 to prepare a set of model guests with and values of (0.6-5.0) × 10 M and (0.6-2.6) × 10 M, respectively. These accessible adamantylphenyl-based binding motifs open a way toward supramolecular components with an outstanding affinity toward β-cyclodextrin. H NMR experiments performed in 30% CaCl/DO at 273 K along with molecular dynamics simulations allowed us to identify two arrangements of the guest@β-CD complexes. The approach, joining experimental and theoretical methods, provided a better understanding of the structure of cyclodextrin complexes and related molecular recognition, which is highly important for the rational design of drug delivery systems, molecular sensors and switches.
最近，人们设计并测试了具有精细亲和力的多主题超分子主体，这些主体对广泛研究的葫芦脲（CBs）和环糊精（CDs）具有亲和力，作为先进超分子系统的功能组件。我们在金刚烷笼和阳离子部分之间使用了各种间隔物，作为调节与 CB7 结合强度的工具，制备了一组模型客体，其 值分别为（0.6-5.0）×10 M 和（0.6-2.6）×10 M。这些可接近的基于金刚烷基苯基的结合基序为具有出色的β-环糊精亲和力的超分子组件开辟了一条道路。在 273 K 下在 30%CaCl/DO 中进行的 H NMR 实验以及分子动力学模拟使我们能够识别客体@β-CD 配合物的两种排列方式。这种结合实验和理论方法的方法，提供了对环糊精配合物结构和相关分子识别的更好理解，这对于药物输送系统、分子传感器和开关的合理设计非常重要。
