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High-affinity host-guest complex of cucurbit[7]uril with a bis(thiazolium) salt
Li,Shengke1; Miao,Xiaoqing1; Wyman,Ian W.2; Li,Ye1; Zheng,Ying1; Wang,Yitao1; Macartney,Donal H.2; Wang,Ruibing1
Source PublicationRSC Advances
AbstractA 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.
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Scopus ID2-s2.0-84936862430
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Cited Times [WOS]:16   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionInstitute of Chinese Medical Sciences
Corresponding AuthorMacartney,Donal H.
Affiliation1.State Key Laboratory of Quality Research in Chinese Medicine,Institute of Chinese Medical Sciences,University of Macau,Taipa,Macao
2.Department of Chemistry,Queen's University,Kingston,90 Bader Lane,K7L 3N6,Canada
First Author AffilicationInstitute of Chinese Medical Sciences
Recommended Citation
GB/T 7714
Li,Shengke,Miao,Xiaoqing,Wyman,Ian 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,Shengke,Miao,Xiaoqing,Wyman,Ian W.,Li,Ye,Zheng,Ying,Wang,Yitao,Macartney,Donal H.,&Wang,Ruibing.(2015).High-affinity host-guest complex of cucurbit[7]uril with a bis(thiazolium) salt.RSC Advances,5(69),56110-56115.
MLA Li,Shengke,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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