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Encapsulation of AGE-Breaker Alagebriumby Cucurbit[7]uril Improvedthe Stability of Both Its Carbonyl α-Hydrogen and Thiazolium C2-Hydrogen
Shengke Li1; Yuan-Fu Ding1,2; Hang Yin1; Chunming Wang1; David Bardelang3; Lian-Hui Wang2; Ruibing Wang1
2016-11
Source PublicationCHEMISTRY-AN ASIAN JOURNAL
ISSN1861-4728
Volume11Issue:21Pages:3126-3133
Abstract

As determined by both (HNMR)-H-1 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-a, in the order of magnitude of 10(5)m(-1), thermodynamically driven by both enthalpy (H=-6.79kcalmol(-1)) and entropy (TS=1.21kcalmol(-1)). For the first time, a dramatic inhibition of keto-enol tautomerism of the carbonyl -hydrogen of ALA has been observed, as evidenced by over an order of magnitude decrease of both the first step rate constant, k(1), and the second step rate constant, k(2), during hydrogen/deuterium exchange in D2O. Meanwhile, as expected, the reactivity of C2-hydrogen was also inhibited significantly, with an upshift of 2.09 pK(a) 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
Indexed BySCI
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000387464400021
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Cited Times [WOS]:11   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionInstitute of Chinese Medical Sciences
Affiliation1.State Key Laboratory of Quality Research in Chinese Medicine Institute of Chinese Medical Sciences University of Macau, Avenida da Universidade,Taipa Macau
2.Key Laboratory for Organic Electronics and Information Displays Institute of Advanced Materials Nanjing University of Posts&Telecommunications 9 Wenyuan Road,Nanjing 210046
3.Aix Marseille Univ,CNRS,ICR Marseille
First Author AffilicationInstitute of Chinese Medical Sciences
Recommended Citation
GB/T 7714
Shengke Li,Yuan-Fu Ding,Hang Yin,et al. Encapsulation of AGE-Breaker Alagebriumby Cucurbit[7]uril Improvedthe Stability of Both Its Carbonyl α-Hydrogen and Thiazolium C2-Hydrogen[J]. CHEMISTRY-AN ASIAN JOURNAL,2016,11(21):3126-3133.
APA Shengke Li.,Yuan-Fu Ding.,Hang Yin.,Chunming Wang.,David Bardelang.,...&Ruibing Wang.(2016).Encapsulation of AGE-Breaker Alagebriumby Cucurbit[7]uril Improvedthe Stability of Both Its Carbonyl α-Hydrogen and Thiazolium C2-Hydrogen.CHEMISTRY-AN ASIAN JOURNAL,11(21),3126-3133.
MLA Shengke Li,et al."Encapsulation of AGE-Breaker Alagebriumby Cucurbit[7]uril Improvedthe Stability of Both Its Carbonyl α-Hydrogen and Thiazolium C2-Hydrogen".CHEMISTRY-AN ASIAN JOURNAL 11.21(2016):3126-3133.
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