ROMP-based Glycopolymers with High Affinity for Mannose-Binding Lectins
Well-defined, highly reactive poly(norbornenyl azlactone)s of controlled length (number-average degree of polymerization were made by ring-opening metathesis polymerization (ROMP) of pure exo-norbornenyl azlactone. These were converted into glycopolymers using a facile postpolymerization modification (PPM) strategy based on click aminolysis of azlactone side groups by amino-functionalized glycosides. Pegylated mannoside, heptyl-mannoside, and pegylated glucoside were used in the PPM. Binding inhibition of the resulting glycopolymers was evaluated against a lectin panel (BC2L-A, FimH, langerin, DC-SIGN, ConA). Inhibition profiles depended on the sugars and the degrees of polymerization. Glycopolymers from pegylated-mannoside-functionalized polynorbornene, with = 100, showed strong binding inhibition, with subnanomolar range inhibitory concentrations (IC50s). Polymers surpassed the inhibitory potential of their monovalent analogues by four to five orders of magnitude thanks to a multivalent (synergistic) effect. Sugar-functionalized poly(norbornenyl azlactone)s are therefore promising tools to study multivalent carbohydrate–lectin interactions and for applications against lectin-promoted bacterial/viral binding to host cells.
About research
Biomacromolecules
2023, 24, 3689-3699
Clément Gonnot, Mathieu Scalabrini, Benoit Roubinet, Célia Ziane, Fabien Boeda, David Deniaud, Ludovic Landemarre, Sébastien G. Gouin, Laurent Fontaine, and Véronique Montembault
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