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Nanomolar cholera toxin inhibitors based on symmetrical pentavalent ganglioside GM1os-sym-corannulenes
Journal article   Peer reviewed

Nanomolar cholera toxin inhibitors based on symmetrical pentavalent ganglioside GM1os-sym-corannulenes

Martin Mattarella, Jaime Garcia-Hartjes, Tom Wennekes, Han Zuilhof and Jay S Siegel
Organic & biomolecular chemistry, Vol.11(26), pp.4333-4339
14/07/2013
DOI: https://doi.org/10.1039/c3ob40438b
PMID: 23736158

Abstract

Antitoxins - chemistry Antitoxins - pharmacology Cholera Toxin - antagonists & inhibitors Cholera Toxin - metabolism G(M1) Ganglioside - analogs & derivatives G(M1) Ganglioside - metabolism G(M1) Ganglioside - pharmacology Galactose - chemistry Galactose - pharmacology Polycyclic Aromatic Hydrocarbons - chemistry Polycyclic Aromatic Hydrocarbons - pharmacology
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.

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