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Encapsulation of AGE-Breaker Alagebrium by Cucurbit[7]uril Improved the Stability of Both Its Carbonyl α-Hydrogen and Thiazolium C2-Hydrogen
Li S.3; Ding Y.-F.3; Yin H.3; Wang C.3; Bardelang D.1; Wang L.-H.2; Wang R.3
2016-11-07
Source PublicationChemistry - An Asian Journal
ISSN1861471X 18614728
Volume11Issue:21Pages:3126-3133
Abstract

As determined by both H NMR and UV/Vis spectroscopic titration, ESI-MS, isothermal titration calorimetry, and DFT molecular modeling, advanced glycation end products (AGE) breaker alagebrium (ALA) formed 1:1 guest–host inclusion complexes with cucurbit[7]uril (CB[7]), with a binding affinity, K, in the order of magnitude of 10 m, thermodynamically driven by both enthalpy (ΔH=−6.79 kcal mol) and entropy (TΔS=1.21 kcal mol). For the first time, a dramatic inhibition of keto–enol tautomerism of the carbonyl α-hydrogen of ALA has been observed, as evidenced by over an order of magnitude decrease of both the first step rate constant, k, and the second step rate constant, k, during hydrogen/deuterium exchange in DO. Meanwhile, as expected, the reactivity of C2-hydrogen was also inhibited significantly, with an upshift of 2.09 pK units. This discovery will not only provide an emerging host molecule to modulate keto–enol tautomerism, but also potentially lead to a novel supramolecular formulation of AGE-breaker ALA for improved stability and therapeutic efficacy.

KeywordCucurbiturils Deuterium Host–guest Systems Kinetics Tautomerism
DOI10.1002/asia.201601153
URLView the original
Indexed BySCI
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000387464400021
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Cited Times [WOS]:13   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionInstitute of Chinese Medical Sciences
Affiliation1.Institut de Chimie Radicalaire
2.Nanjing University of Post and TeleCommunications
3.University of Macau
First Author AffilicationUniversity of Macau
Recommended Citation
GB/T 7714
Li S.,Ding Y.-F.,Yin H.,et al. Encapsulation of AGE-Breaker Alagebrium by Cucurbit[7]uril Improved the Stability of Both Its Carbonyl α-Hydrogen and Thiazolium C2-Hydrogen[J]. Chemistry - An Asian Journal,2016,11(21):3126-3133.
APA Li S..,Ding Y.-F..,Yin H..,Wang C..,Bardelang D..,...&Wang R..(2016).Encapsulation of AGE-Breaker Alagebrium by Cucurbit[7]uril Improved the Stability of Both Its Carbonyl α-Hydrogen and Thiazolium C2-Hydrogen.Chemistry - An Asian Journal,11(21),3126-3133.
MLA Li S.,et al."Encapsulation of AGE-Breaker Alagebrium by Cucurbit[7]uril Improved the Stability of Both Its Carbonyl α-Hydrogen and Thiazolium C2-Hydrogen".Chemistry - An Asian Journal 11.21(2016):3126-3133.
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