Thiol‐ene and thiol‐yne‐based synthesis of glycodendrimers as nanomolar inhibitors of wheat germ agglutinin |
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| Authors: | Mattia Ghirardello Kim Öberg Samuele Staderini Olivier Renaudet Nathalie Berthet Pascal Dumy Yvonne Hed Alberto Marra Michael Malkoch Alessandro Dondoni |
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| Institution: | 1. Dipartimento di Scienze Chimiche e Farmaceutiche, Università di Ferrara, , 44121 Ferrara, Italy;2. Division of Coating Technology, KTH The Royal Institute of Technology, School of Chemical Science and Engineering, , SE‐10044 Stockholm, Sweden;3. Département de Chimie Moléculaire, UMR CNRS 5250, Université Joseph Fourier, 570 Rue de la chimie, BP 53, , 38041 Grenoble cedex 9, France;4. Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, Université Montpellier 2, Ecole Nationale Supérieure de Chimie de Montpellier, 8 Rue de l'Ecole Normale, , France;5. Interdisciplinary Center for the Study of Inflammation, Università di Ferrara, , 44100 Ferrara, Italy |
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| Abstract: | Alkene and alkyne functional polyester‐based dendrimers of generation 1 to 4 have been prepared and reacted under free‐radical conditions with 2‐acetamido‐2‐deoxy‐1‐thio‐β‐D ‐glucose (GlcNAc‐SH). As the alkene‐dendrimers underwent the addition of one thiyl radical per ene group whereas each yne group of alkyne‐dendrimers was saturated by two thiyl radicals, a collection of glycodendrimers with glycan density ranging from six to ninety‐six GlcNAc per dendrimer was obtained. The recognition properties of the prepared glycodendrimers toward the wheat germ agglutinin (WGA) were evaluated by enzyme‐linked lectin assay (ELLA). The eight glycodendrimers were excellent ligands showing IC50 values in the nanomolar range and relative potencies per sugar unit up to 2.27 e6 when compared to monosaccharidic GlcNAc used as monovalent reference. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014 , 52, 2422–2433 |
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| Keywords: | carbohydrates chiral dendrimers photochemistry radical reactions |
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