Selectivity among two lectins: probing the effect of topology, multivalency and flexibility of "clicked" multivalent glycoclusters |
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Authors: | Cecioni Samy Faure Sophie Darbost Ulrich Bonnamour Isabelle Parrot-Lopez Hélène Roy Olivier Taillefumier Claude Wimmerová Michaela Praly Jean-Pierre Imberty Anne Vidal Sébastien |
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Institution: | Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, Laboratoire de Chimie, Organique 2-Glycochimie, UMR5246, Université Claude Bernard Lyon 1 and CNRS, 43 Boulevard du 11 Novembre 1918, 69622 Villeurbanne, France. |
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Abstract: | The design of multivalent glycoconjugates has been developed over the past decades to obtain high-affinity ligands for lectin receptors. While multivalency frequently increases the affinity of a ligand for its lectin through the so-called "glycoside cluster effect", the binding profiles towards different lectins have been much less investigated. We have designed a series of multivalent galactosylated glycoconjugates and studied their binding properties towards two lectins, from plant and bacterial origins, to determine their potential selectivity. The synthesis was achieved through copper(I)-catalysed azide-alkyne cycloaddition (CuAAC) under microwave activation between propargylated multivalent scaffolds and an azido-functionalised carbohydrate derivative. The interactions of two galactose-binding lectins from Pseudomonas aeruginosa (PA-IL) and Erythrina cristagalli (ECA) with the synthesized glycoclusters were studied by hemagglutination inhibition assays (HIA), surface plasmon resonance (SPR) and isothermal titration microcalorimetry (ITC). The results obtained illustrate the influence of the scaffold's geometry on the affinity towards the lectin and also on the relative potency in comparison with a monovalent galactoside reference probe. |
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Keywords: | calixarenes carbohydrates glycoclusters lectins multivalency |
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