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Beta-Cyclodextrin Duplexes That Are Connected through Two Disulfide Bonds: Potent Hosts for the Complexation of Organic Molecules
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SYSNO ASEP 0383761 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Beta-Cyclodextrin Duplexes That Are Connected through Two Disulfide Bonds: Potent Hosts for the Complexation of Organic Molecules Author(s) Grishina, Anastasia (UOCHB-X) RID
Stanchev, Stancho (UOCHB-X) RID, ORCID
Kumprecht, Lukáš (UOCHB-X)
Buděšínský, Miloš (UOCHB-X) RID, ORCID
Pojarová, Michaela (FZU-D) RID, ORCID
Dušek, Michal (FZU-D) RID, ORCID, SAI
Rumlová, Michaela (UOCHB-X) RID
Křížová, Ivana (UOCHB-X) RID
Rulíšek, Lubomír (UOCHB-X) RID, ORCID
Kraus, Tomáš (UOCHB-X) RID, ORCIDNumber of authors 10 Source Title Chemistry - A European Journal. - : Wiley - ISSN 0947-6539
Roč. 18, č. 39 (2012), s. 12292-12304Number of pages 13 s. Language eng - English Country DE - Germany Keywords cucurbiturils ; cyclodextrins ; duplexes ; host-guest systems ; sulfur Subject RIV CF - Physical ; Theoretical Chemistry Institutional support UOCHB-X - RVO:61388963 ; FZU-D - RVO:68378271 UT WOS 000308879000018 DOI 10.1002/chem.201201239 Annotation New tubular host molecules, which are composed of two beta-cyclodextrin macrocycles that are connected through two disulfide bonds, have been prepared by the air-promoted oxidation of 6I,6IV-dideoxy-6I,6IV-disulfanyl-beta-cyclodextrin in aqueous solution. This reaction leads to three products: monomeric intramolecular disulfide and two dimeric species, which are termed as non-eclipsed and eclipsed cyclodextrin duplexes. Oxidation at a concentration of the starting thiol of 0.1 mM gave the intramolecular disulfide as the major product whereas a concentration in the millimolar range afforded the dimeric species as the dominant products. The tubular structure of the non-eclipsed isomer was unequivocally determined by X-ray analysis. The binding affinities of the duplexes to a wide range of compounds, including fluorescent dyes and clinically used drugs Imatinib and Esomeprazol, were studied in water by ITC. For most guest compounds, the experimentally determined Ka values were in the range 107-108M-1. These binding affinities are significantly higher than those found in the literature for analogous complexes with native cyclodextrins. In cases of binding of neutral or anionic guest molecules cyclodextrin duplexes outperformed cucurbiturils. A complex between a duplex and Nile blue was used to investigate its ability to penetrate the cytoplasmic membrane of HeLa cells. We found that the complex accumulated in the cell membrane but did not pass into cytosol. Importantly, the complex did not decompose to a significant extent under high dilution in the cellular environment. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2013
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