title: Fullerene sugar balls: a new class of biologically active fullerene derivatives.
abstract: Among the large variety of bioactive C60 derivatives, fullerene derivatives substituted with sugar residues, that is, glycofullerenes, are of particular interest. The sugar residues are not only solubilizing groups; their intrinsic biological properties also provide additional appealing features to the conjugates. The most recent advances in the synthesis and the biological applications of glycofullerenes are summarized in the present review article with special emphasis on globular glycofullerenes, that is, fullerene sugar balls, constructed on a hexa-substituted fullerene scaffold. The high local concentration of carbohydrates around the C60 core in fullerene sugar balls is perfectly suited to the binding of lectins through the "glycoside cluster effect", and these compounds are potential anti-adhesive agents against bacterial infection. Moreover, mannosylated fullerene sugar balls have shown antiviral activity in an Ebola pseudotyped infection model. Finally, when substituted with peripheral iminosugars, dramatic multivalent effects have been observed for glycosidase inhibition. These unexpected observations have been rationalized by the interplay of interactions involving the catalytic site of the enzyme and non-glycone binding sites with lectin-like abilities.
authors.affiliation: Laboratoire de Chimie des Matériaux Moléculaires, Université de Strasbourg et CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux, 25 rue Becquerel, 67087 Strasbourg Cedex 2 (France).
authors.forename: Iwona
authors.initials: I
authors.lastname: Nierengarten
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Nierengarten
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D000998:Antiviral Agents / Q000737:chemistry* / Q000494:pharmacology; D001422:Bacterial Adhesion / Q000187:drug effects; D029043:Ebolavirus / Q000187:drug effects; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D037741:Fullerenes / Q000737:chemistry* / Q000494:pharmacology; D006001:Glycoconjugates / Q000737:chemistry* / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D050111:Imino Sugars / Q000737:chemistry* / Q000494:pharmacology; D037181:Lectins, C-Type / Q000378:metabolism; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D000900:Anti-Bacterial Agents; D000998:Antiviral Agents; D004791:Enzyme Inhibitors; D037741:Fullerenes; D006001:Glycoconjugates; D050111:Imino Sugars; D037181:Lectins, C-Type; D008024:Ligands; D006026:Glycoside Hydrolases
keywords: fullerenes; inhibitors; lectins; multivalent ligands; sugar