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Article Dans Une Revue Nature Chemistry Année : 2016

Synthesis of giant globular multivalent glycofullerenes as potent inhibitors in a model of Ebola virus infection

Joanna Luczkowiak
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Iwona Nierengarten
Stéphane Vincent
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Rafael Delgado
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Résumé

The use of multivalent carbohydrate compds. 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 compds. 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-sol. tridecafullerenes decorated with 120 peripheral carbohydrate subunits, so-called 'super-balls', that can be synthesized efficiently from hexakis adducts of [60]fullerene in one step by using copper-catalyzed azide-alkyne cycloaddn. click chem. Infection assays show that these superballs are potent inhibitors of cell infection by an artificial Ebola virus with half-max. inhibitory concns. in the sub-nanomolar range.
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hal-02478562 , version 1 (24-03-2024)

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Antonio Munoz, David Sigwalt, Beatriz Illescas, Joanna Luczkowiak, Laura Rodriguez-Perez, et al.. Synthesis of giant globular multivalent glycofullerenes as potent inhibitors in a model of Ebola virus infection. Nature Chemistry, 2016, 8, pp.50-57. ⟨10.1038/nchem.2387⟩. ⟨hal-02478562⟩
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