Modes of Micromolar Host–Guest Binding of β-Cyclodextrin Complexes Revealed by NMR Spectroscopy in Salt Water
| Autor: | Ivo Durník, Andrea Čablová, Aneta Hromádková, Josef Tomeček, Lenka Dastychová, Michal Rouchal, Radek Marek, Jan Novotný, Zdeňka Prucková, Robert Vícha, Petr Kulhánek |
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| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Cyclodextrins Magnetic Resonance Spectroscopy Molecular Structure Molecular model Cyclodextrin 010405 organic chemistry Adamantane beta-Cyclodextrins Organic Chemistry Rational design Supramolecular chemistry Water Nuclear magnetic resonance spectroscopy 010402 general chemistry 01 natural sciences Combinatorial chemistry 3. Good health 0104 chemical sciences chemistry.chemical_compound Molecular recognition chemistry Moiety |
| Zdroj: | The Journal of Organic Chemistry. 86:4483-4496 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | Multitopic supramolecular guests with finely tuned affinities toward widely explored cucurbit[n]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 KCB7 and Kβ-CD values of (0.6-5.0) × 1010 M-1 and (0.6-2.6) × 106 M-1, respectively. These accessible adamantylphenyl-based binding motifs open a way toward supramolecular components with an outstanding affinity toward β-cyclodextrin. 1H NMR experiments performed in 30% CaCl2/D2O 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. |
| Databáze: | OpenAIRE |
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