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

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Chinese Chemical Letters 2023年第2期34卷 214-218页

作者： Zhiping Liu Fanny Demontrond Anne Imberty Andrew C.-H.Sue Sébastien Vidal Hongxia Zhao Tianjin Key Lab for Modern Drug Delivery and High-Efficiency School of Pharmaceutical Science and TechnologyTianjin UniversityTianjin 300072China Institut de Chimie et Biochimie Moléculaires et Supramoléculaires Laboratoire de Chimie Organique 2-GlycochimieUMR 5246CNRSUniversitéClaude Bernard Lyon 1Universitéde LyonVilleurbanne 69622France CNRS Univ.Grenoble AlpesCERMAVGrenoble 38000France College of Chemistry and Chemical Engineering Xiamen UniversityXiamen 361005China CNRS Institut de Chimie des Substances NaturellesUniversitéParis-SaclayUPR 2301Gif-sur-Yvette 91198France

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 Lec A and Lec B from Pseudomonas aeruginosa and concanavalin A(Con A), were evaluated subsequently by isothermal titration calorimetric studies. Most of these isomerfree RD-P[5] pentavalent glycoclusters, except the fucosylated ones, display good affinities to ***, 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.

关键词： glycocluster Lectin Pillararene Multivalency Constitutional purity

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Synthesis of Glutamic Acid-based Cluster Galactosides and Their Binding Affinities with Liver Cells

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Chinese Journal of Chemistry 2004年第5期22卷 482-486页

作者：张晓茹李英霞褚世栋丁宁李春霞管华诗 Institute of Marine Drugs and Food Ocean University of China Qingdao Shandong 266003 China

Structurally well defined di-, tri- and tetra-valent cluster galactosides were synthesized in a convenient way. Oligo-glutamic acids were assembled as scaffolds. The presence of amine groups in these three ligands is expected to couple with drugs or genes for delivery. The binding affinities of these cluster galactoses to liver cells were de-termined by in vitro binding studies. Among them, the tetravalent cluster galactose (19) showed the highest affinity to liver cell. It is therefore a promising targeting device for the specific delivery of drugs or genes to parenchymal liver cells.

关键词： glycocluster cluster galactoside multivalent effect glutamic acid

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