Citation: Zhiping Liu, Fanny Demontrond, Anne Imberty, Andrew C.-H. Sue, Sébastien Vidal, Hongxia Zhao. Rim-differentiation vs. mixture of constitutional isomers: A binding study between pillar[5]arene-based glycoclusters and lectins from pathogenic bacteria[J]. Chinese Chemical Letters, ;2023, 34(2): 107872. doi: 10.1016/j.cclet.2022.107872 shu

Rim-differentiation vs. mixture of constitutional isomers: A binding study between pillar[5]arene-based glycoclusters and lectins from pathogenic bacteria

Zhiping Liu ^{a, 1} ,
Fanny Demontrond ^{b, 1} ,
Anne Imberty ^c ,
Andrew C.-H. Sue ^{d, *,} ,
Sébastien Vidal ^{b, e, **,} ,
Hongxia Zhao ^{a, *,}

a.
Tianjin Key Lab for Modern Drug Delivery and High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China
b.
Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, Laboratoire de Chimie Organique 2-Glycochimie, UMR 5246, CNRS, Université Claude Bernard Lyon 1, Université de Lyon, Villeurbanne 69622, France
c.
CNRS, Univ. Grenoble Alpes, CERMAV, Grenoble 38000, France
d.
College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China
e.
CNRS, Institut de Chimie des Substances Naturelles, Université Paris-Saclay, UPR 2301, Gif-sur-Yvette 91198, France

^☆

^**

andrewsue@xmu.edu.cn

msebastien.vidal@cnrs.fr

zhaohongxia@tju.edu.cn

Received Date: 9 August 2022
Revised Date: 26 September 2022
Accepted Date: 29 September 2022
Available Online: 1 October 2022

Figures(4)

Macrocycle-based glycoclusters, on account of their promising anti-adhesive properties against bacteria, are potential therapeutic alternatives to classic antibiotics through the much less explored anti-adhesive strategy. In this study, a series of constitutionally-pure pentavalent glycoclusters was prepared by conjugating assorted azido-carbohydrates onto a penta-propargyl rim-differentiated pillar[5]arene (RD-P[5]) scaffold through Cu(I)-catalyzed azide–alkyne cycloaddition "click" reactions. Their binding towards therapeutically relevant bacterial lectins, such as LecA and LecB from Pseudomonas aeruginosa and concanavalin A (ConA), were evaluated subsequently by isothermal titration calorimetric studies. Most of these isomer-free RD-P[5] pentavalent glycoclusters, except the fucosylated ones, display good affinities to lectins. Nonetheless, the dissociation constants observed are similar to those displayed by an analogous pentavalent glycocluster consisting of four P[5] constitutional isomers, in which the RD-P[5] component merely accounts for 7% in the mixture. Our results revealed that high constitutional purity is not essential for achieving effective multivalent interactions between P[5]-based glycoclusters and lectins, presumably as a result of the conformationally labile nature of the P[5] scaffold. This information provides valuable design principles for low-cost and facile syntheses of glycosylated P[5]s for biomedical applications.
- Glycocluster,
- Lectin,
- Pillararene,
- Multivalency,
- Constitutional purity
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