Eight symmetric and pentavalent corannulene derivatives were functionalized with galactose and the ganglioside GM1-oligosaccharide (GM1os) via copper-catalyzed alkyne-azide cycloaddition (CuAAC) reactions. The compounds were evaluated for their ability to inhibit the binding of the pentavalent cholera toxin to its natural ligand, ganglioside GM1. In this assay, all ganglioside GM1os-sym-corannulenes proved to be highly potent nanomolar inhibitors of cholera toxin.
- heat-labile enterotoxin
- multivalent ligands
- gm1 mimics
Mattarella, M., Garcia-Hartjes, J., Wennekes, T., Zuilhof, H., & Siegel, J. S. (2013). Nanomolar cholera toxin inhibitors based on symmetrical pentavalent ganglioside GM1os-sym-corannulenes. Organic & Biomolecular Chemistry, 11(26), 4333-4339. https://doi.org/10.1039/c3ob40438b