Amphiphilic glycan-functionalized oligomers are derived by solid-phase polymer synthesis and applied in both, self-assembled micelles as well as giant unilamellar vesicles, as simplified models of the cell's glycocalyx. Additionally, an aggregation-induced luminophore is introduced into the amphiphilic glycomacromolecules showing no fluorescence when the molecule is free in solution. Combining glycomacromolecules carrying a binding glycan motif and the luminophore with glycomacromolecules or other amphiphiles with no binding motifs and no luminophore in self-assembled structures, micelles and vesicles exhibiting no or only very little fluorescence are obtained. Only upon clustering of the binding glycan motifs through interaction with a multivalent lectin receptor, an increase in fluorescence is observed. Thus, clustering events within these self-assembled structures can be detected and localized.
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