Organizing multivalency in carbohydrate recognition

Müller, Christian; Despras, Guillaume; Lindhorst, Thisbe K.

doi:10.1039/c6cs00165c

Cited by 199 publications

(156 citation statements)

References 181 publications

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“…a protein simultaneously binds to two or more different types of receptors). [7] Due to the complexity of hetero-multivalency, most studies have focused on homo-multivalency. However, homo-multivalent models neglect the inherent heterogeneity of cell membranes.…”

Section: Introductionmentioning

confidence: 99%

Hetero-multivalent binding of cholera toxin subunit B with glycolipid mixtures

Krishnan

Singla

Lee

et al. 2017

Colloids and Surfaces B: Biointerfaces

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GM1 has generally been considered as the major receptor that binds to cholera toxin subunit B (CTB) due to its low dissociation constant. However, using a unique nanocube sensor technology, we have shown that CTB can also bind to other glycolipid receptors, fucosyl-GM1 and GD1b. Additionally, we have demonstrated that GM2 can contribute to CTB binding if present in a glycolipid mixture with a strongly binding receptor (GM1/fucosyl-GM1/GD1b). This hetero-multivalent binding result was unintuitive because the interaction between CTB and pure GM2 is negligible. We hypothesized that the reduced dimensionality of CTB-GM2 binding events is a major cause of the observed CTB binding enhancement. Once CTB has attached to a strong receptor, subsequent binding events are confined to a 2D membrane surface. Therefore, even a weak GM2 receptor could now participate in second or higher binding events because its surface reaction rate can be up to 104 times higher than the bulk reaction rate. To test this hypothesis, we altered the surface reaction rate by modulating the fluidity and heterogeneity of the model membrane. Decreasing membrane fluidity reduced the binding cooperativity between GM2 and a strong receptor. Our findings indicated a new protein-receptor binding assay, that can mimic complex cell membrane environment more accurately, is required to explore the inherent hetero-multivalency of the cell membrane. We have thus developed a new membrane perturbation protocol to efficiently screen receptor candidates involved in hetero-multivalent protein binding.

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Section: Introductionmentioning

confidence: 99%

Hetero-multivalent binding of cholera toxin subunit B with glycolipid mixtures

Krishnan

Singla

Lee

et al. 2017

Colloids and Surfaces B: Biointerfaces

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“…[23] Current targeting strategies involve the use of antibodies, [24] aptamers, [25] or small molecules such as vancomycin. [34,35] Multivalent glycoconjugates, such as glycoclusters, glycopeptides, and glyconanoparticles, have been employed as lectin ligands for inhibition of bacterial adhesion and biofilm formation, [36][37][38][39][40] decontamination of bacteria, [41] and blockage of host cell invasion by bacteria. [27][28][29] Numerous strains of bacteria express carbohydrate-binding proteins, termed lectins, on their surfaces to mediate critical physiological and pathological activities, for example, adhesion to host cells, biofilm formation, and infection.…”

Section: Doi: 101002/adtp201900052mentioning

confidence: 99%

Glycosylated Copper Sulfide Nanocrystals for Targeted Photokilling of Bacteria in the Near‐Infrared II Window

Hou

Mahadevegowda

Cuong

et al. 2019

Advanced Therapeutics

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Photothermal and photodynamic therapies are established as alternative approaches to combating bacterial infections; however, the heat and reactive oxygen species generated by the photoagents act on both normal and bacterial cells. A targeting strategy is thus required to minimize side effects and enhance the antibacterial efficiency. Glycoconjugates specifically interacting with bacterial lectins have emerged as a new class of materials for targeting bacteria. In this paper, galactosylated plasmonic copper sulfide nanocrystals (Cu 2−x S NCs) are used to target Pseudomonas aeruginosa via galactose-LecA interactions and kill the bacteria by simultaneous photothermal and photodynamic therapy. Galactosylated Cu 2−x S NCs are obtained by functionalizing the nanocrystals with tri-thiogalactoside glycoclusters. The excellent specificity of galactosylated nanoparticles toward LecA with a LecA-deficient P. aeruginosa strain as the control is first demonstrated. Afterward, a laser in the near-infrared II window is used to kill the bacteria, and the critical role of targeted binding in efficient killing of bacteria is highlighted. This approach can be readily generalized to the targeting of other pathogens which have highly specific carbohydrate-binding lectins.

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“…These triazole-linked glycomacrocycles showed remarkable reaction rate accelerations for CuSO 4 mediated azide and alkyne cycloaddition reactions in aqueous mixtures. [14,[16][17][18] The CuAAC products, typically 1,4-disubstituted 1,2,3-triazoles, are useful heterocycles that are not passive linkers, they also have properties leading to biological activities, as ligands in catalysis, sensors for guest recognitions, and in preparation of functional supramolecular assemblies. The benzoylated macrocycles with three methylene linkage at anomeric positions were the most effective among the eight macrocycles.…”

Section: Introductionmentioning

confidence: 99%

Syntheses of Bis‐Triazole Linked Carbohydrate Based Macrocycles and Their Applications for Accelerating Copper Sulfate Mediated Click Reaction

et al. 2019

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Macrocyclic compounds play an important role in many research fields including drug discovery and development, bioorganic chemistry, and materials sciences. Carbohydrate‐based macrocycles are important compounds with unique structures and many potential applications. In this study, we have designed and synthesized a series of 1,2,3‐triazole linked and pyranose embedded macrocycles in short steps through the copper (I) catalyzed azide and alkyne cycloaddition reactions (CuAACs). Eight non‐symmetrical glucosamine based and bis‐triazole linked macrocycles have been synthesized starting from the readily available N‐acetyl‐d‐glucosamine. These triazole‐linked glycomacrocycles showed remarkable reaction rate accelerations for CuSO4 mediated azide and alkyne cycloaddition reactions in aqueous mixtures. Several azides including a sugar azide, which react sluggishly with alkynes, have been accelerated with the synthesized macrocycles. The benzoylated macrocycles with three methylene linkage at anomeric positions were the most effective among the eight macrocycles.

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Organizing multivalency in carbohydrate recognition

Cited by 199 publications

References 181 publications

Hetero-multivalent binding of cholera toxin subunit B with glycolipid mixtures

Hetero-multivalent binding of cholera toxin subunit B with glycolipid mixtures

Glycosylated Copper Sulfide Nanocrystals for Targeted Photokilling of Bacteria in the Near‐Infrared II Window

Syntheses of Bis‐Triazole Linked Carbohydrate Based Macrocycles and Their Applications for Accelerating Copper Sulfate Mediated Click Reaction

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