title: Nanomolar cholera toxin inhibitors based on symmetrical pentavalent ganglioside GM1os-sym-corannulenes.
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.
authors.affiliation: Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland. jss@oci.uzh.ch.
authors.forename: Martin
authors.initials: M
authors.lastname: Mattarella
authors.affiliation: Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB, Wageningen, The Netherlands.
authors.forename: Jaime
authors.initials: J
authors.lastname: Garcia-Hartjes
authors.affiliation: Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB, Wageningen, The Netherlands.
authors.forename: Tom
authors.initials: T
authors.lastname: Wennekes
authors.affiliation: Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB, Wageningen, The Netherlands and Department of Chemical and Materials Engineering, King Abdulaziz University, Jeddah, Saudi Arabia. han.zuilhof@wur.nl.
authors.forename: Han
authors.initials: H
authors.lastname: Zuilhof
authors.affiliation: Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland. jss@oci.uzh.ch.
authors.forename: Jay S
authors.initials: JS
authors.lastname: Siegel
mesh_terms: D000992:Antitoxins / Q000737:chemistry* / Q000494:pharmacology; D002772:Cholera Toxin / Q000037:antagonists & inhibitors* / Q000378:metabolism; D005677:G(M1) Ganglioside / Q000031:analogs & derivatives* / Q000378:metabolism / Q000494:pharmacology; D005690:Galactose / Q000737:chemistry* / Q000494:pharmacology; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D000992:Antitoxins; D011084:Polycyclic Aromatic Hydrocarbons; C434863:corannulene; D005677:G(M1) Ganglioside; D002772:Cholera Toxin; D005690:Galactose