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High-affinity host-guest complex of cucurbit[7]uril with a bis(thiazolium) salt
Li S.1; Miao X.1; Wyman I.W.2; Li Y.1; Zheng Y.1; Wang Y.1; Macartney D.H.2; Wang R.1
2015
Source PublicationRSC Advances
ISSN2046-2069
Volume5Issue:69Pages:56110-56115
Other Abstract

A biologically- and pharmaceutically-relevant bis(thiazolium) dication model compound, α,α′-bis(thiazolium)-p-xylene (BTX), forms a strong 1:1 host-guest inclusion complex with cucurbit[7]uril (CB[7]). The complexation stoichiometry, binding affinity and geometry were studied via H NMR and UV-visible titrations, ESI-MS, and molecular modeling (ab initio calculations). The hydrogen/deuterium exchange reactions of the C(2)-proton of BTX were conducted in the absence and presence of CB[7] in DO at 25 °C and at an ionic strength of 0.20 M. The inhibition of C(2)-H/D exchange of the guest bis(thiazolium) dication upon complexation with CB[7] exhibited a second-order rate constant that decreased by more than four-fold in the presence of CB[7]. The supramolecular-controlled stability of thiazolium cations through complexation with CB[7] host molecules is anticipated to have applications for stability enhancement of thiazolium based drugs and to potentially draw interest in the application of CB[n] host molecules with regard to the formulation and delivery of these drugs.

DOIhttps://doi.org/10.1039/c5ra04468e
URLView the original
Indexed BySCI
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000357803200059
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Cited Times [WOS]:16   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionInstitute of Chinese Medical Sciences
Corresponding AuthorMacartney D.H.; Wang R.
Affiliation1.State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Taipa, Macau, China
2.Department of Chemistry, Queen's University, 90 Bader Lane, Kingston, ON K7L 3N6, Canada
First Author AffilicationInstitute of Chinese Medical Sciences
Corresponding Author AffilicationInstitute of Chinese Medical Sciences
Recommended Citation
GB/T 7714
Li S.,Miao X.,Wyman I.W.,et al. High-affinity host-guest complex of cucurbit[7]uril with a bis(thiazolium) salt[J]. RSC Advances,2015,5(69):56110-56115.
APA Li S..,Miao X..,Wyman I.W..,Li Y..,Zheng Y..,...&Wang R..(2015).High-affinity host-guest complex of cucurbit[7]uril with a bis(thiazolium) salt.RSC Advances,5(69),56110-56115.
MLA Li S.,et al."High-affinity host-guest complex of cucurbit[7]uril with a bis(thiazolium) salt".RSC Advances 5.69(2015):56110-56115.
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