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

M. Mattarella, J. Garcia-Hartjes, T. Wennekes, H. Zuilhof, J.S. Siegel

Research output: Contribution to journal › Article › Academic › peer-review

17 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)4333-4339
JournalOrganic & Biomolecular Chemistry
Volume11
Issue number26
DOIs
Publication statusPublished - 2013

Keywords

  • heat-labile enterotoxin
  • receptor-binding
  • multivalent ligands
  • gm1 mimics
  • design
  • corannulene
  • derivatives
  • dendrimers
  • subunit

Access to Document

Fingerprint Dive into the research topics of 'Nanomolar cholera toxin inhibitors based on symmetrical pentavalent ganglioside GM1os-sym-corannulenes'. Together they form a unique fingerprint.

Cite this