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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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作者 Zhiping Liu Fanny Demontrond +3 位作者 Anne Imberty Andrew C.-H.Sue Sébastien Vidal Hongxia Zhao 《Chinese Chemical Letters》 SCIE CAS CSCD 2023年第2期214-218,共5页
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 strate... 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 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. 展开更多
关键词 glycocluster LECTIN Pillararene MULTIVALENCY Constitutional purity
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Fluorescence quenching of triazatruxene-based glycocluster induced by peanut agglutinin lectin
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作者 Ke-Rang Wang Hong-Wei An +2 位作者 Dan Han Feng Qian Xiao-Liu Li 《Chinese Chemical Letters》 SCIE CAS CSCD 2013年第6期467-470,共4页
A novel triazatruxene-based fluorescent glycocluster was synthesized and its selective binding interactions with PNA lectin were investigated by fluorescence spectroscopy,CD spectroscopy,and a turbidity assay.The glyc... A novel triazatruxene-based fluorescent glycocluster was synthesized and its selective binding interactions with PNA lectin were investigated by fluorescence spectroscopy,CD spectroscopy,and a turbidity assay.The glycocluster exhibited a strong binding affinity for PNA lectin with a Stern-Volmer quenching constant of 5.8×10^5 mol^-1L 展开更多
关键词 Triazatruxene glycocluster Fluorescence quenching Peanut agglutinin
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One-pot Synthesis of Divalent and Trivalent Cluster Mannosides via Ugi Four-component Reaction
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作者 Xiao Ru ZHANG Ying Xia LI +2 位作者 Shi Dong CHU Kun Yu YU Hua Shi GUAN 《Chinese Chemical Letters》 SCIE CAS CSCD 2003年第11期1130-1132,共3页
The Ugi four-component reaction (U-4CR) was utilized to prepare divalent and trivalent cluster mannosides. Thus, two target compounds 6 and 8 were obtained efficiently using carboxymethyl 2, 3, 4, 6-tetra-O-acetyl--D-... The Ugi four-component reaction (U-4CR) was utilized to prepare divalent and trivalent cluster mannosides. Thus, two target compounds 6 and 8 were obtained efficiently using carboxymethyl 2, 3, 4, 6-tetra-O-acetyl--D-mannopyranoside 4 as acid component, and 1, 6-hexanediamine or tris(2-aminoethyl)amine as the multivalent scaffolds. 展开更多
关键词 Ugi reactions cluster mannosides glycocluster.
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Synthesis of Glutamic Acid-based Cluster Galactosides and Their Binding Affinities with Liver Cells
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作者 张晓茹 李英霞 +3 位作者 褚世栋 丁宁 李春霞 管华诗 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2004年第5期482-486,共5页
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 ... 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. 展开更多
关键词 glycocluster cluster galactoside multivalent effect glutamic acid
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