title: Synthesis of giant globular multivalent  glycofullerenes as potent inhibitors in a model of  Ebola virus infection.
abstract: The use of multivalent carbohydrate compounds to block cell-surface lectin receptors is a promising strategy to inhibit the entry of pathogens into cells and could lead to the discovery of novel antiviral agents. One of the main problems with this approach, however, is that it is difficult to make compounds of an adequate size and multivalency to mimic natural systems such as viruses. Hexakis adducts of [60]fullerene are useful building blocks in this regard because they maintain a globular shape at the same time as allowing control over the size and multivalency. Here we report water-soluble tridecafullerenes decorated with 120 peripheral carbohydrate subunits, so-called 'superballs', that can be synthesized efficiently from hexakis adducts of [60]fullerene in one step by using copper-catalysed azide–alkyne cycloaddition click chemistry. Infection assays show that these superballs are potent inhibitors of cell infection by an artificial Ebola virus with half-maximum inhibitory concentrations in the subnanomolar range.
authors.forename: Antonio
authors.initials: A
authors.lastname: Muñoz
authors.forename: David
authors.initials: D
authors.lastname: Sigwalt
authors.forename: Beatriz M
authors.initials: BM
authors.lastname: Illescas
authors.forename: Joanna
authors.initials: J
authors.lastname: Luczkowiak
authors.forename: Laura
authors.initials: L
authors.lastname: Rodríguez-Pérez
authors.forename: Iwona
authors.initials: I
authors.lastname: Nierengarten
authors.forename: Michel
authors.initials: M
authors.lastname: Holler
authors.forename: Jean-Serge
authors.initials: JS
authors.lastname: Remy
authors.forename: Kevin
authors.initials: K
authors.lastname: Buffet
authors.forename: Stéphane P
authors.initials: SP
authors.lastname: Vincent
authors.forename: Javier
authors.initials: J
authors.lastname: Rojo
authors.forename: Rafael
authors.initials: R
authors.lastname: Delgado
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Nierengarten
authors.forename: Nazario
authors.initials: N
authors.lastname: Martín
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001386:Azides / Q000737:chemistry; D057930:Click Chemistry; D029043:Ebolavirus / Q000187:drug effects*; D037741:Fullerenes / Q000737:chemistry* / Q000494:pharmacology; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D057809:HEK293 Cells; D019142:Hemorrhagic Fever, Ebola / Q000188:drug therapy*; D006801:Humans; D019169:Jurkat Cells; D008358:Mannose / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000998:Antiviral Agents; D001386:Azides; D037741:Fullerenes; D006001:Glycoconjugates; D008358:Mannose