Modes of Micromolar Host-Guest Binding of beta-Cyclodextrin Complexes Revealed by NMR Spectroscopy in Salt Water

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Publikace nespadá pod Ústav výpočetní techniky, ale pod Středoevropský technologický institut. Oficiální stránka publikace je na webu muni.cz.

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TOMEČEK Josef ČABLOVÁ Andrea HROMÁDKOVÁ Aneta NOVOTNÝ Jan MAREK Radek DURNÍK Ivo KULHÁNEK Petr PRUCKOVÁ Zdeňka ROUCHAL Michal DASTYCHOVÁ Lenka VÍCHA Robert

Rok publikování 2021
Druh Článek v odborném periodiku
Časopis / Zdroj The Journal of Organic Chemistry
Fakulta / Pracoviště MU

Středoevropský technologický institut

Citace
www https://doi.org/10.1021/acs.joc.0c02917
Doi http://dx.doi.org/10.1021/acs.joc.0c02917
Klíčová slova host-guest complex;cyclodextrin;NMR spectroscopy;molecular modeling;binding;salt water
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 K(CB7) and K(beta-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 beta-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@beta-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.
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