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

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

Langmuir and Langmuir-Blodgett Films from Amphiphilic Pillar[5]arene-Containing [2]Rotaxanes

Amphiphilic pillar[5]arene-containing [2]rotaxanes have been prepared and fully characterized. In the particular case of the [2]rotaxane incorporating a 1,4-diethoxypillar[5]arene subunit, the structure of the compound was confirmed by X-ray crystal structure analysis. Owing to a good hydrophilic/hydrophobic balance, stable Langmuir films have been obtained for these rotaxanes and the size of the peripheral alkyl chains on the pillar[5]arene subunit has a dramatic influence on the reversibility during compression-decompression cycles. Indeed, when these are small enough, molecular reorganization of the rotaxane by gliding motions are capable of preventing strong - interactions between neighboring macrocycles in the thin film

Aufbau des ersten Fulleren‐haltigen [2]Catenans durch Selbstorganisation

Als wirksames Templat zum Aufbau eines Cyclobis(paraquat‐p‐phenylen)‐Cyclophans unter Bildung des [2]Catenans 1 dient der in definierter Weise kovalent mit C60 verknüpfte Kronenether Bis(p‐phenylen)‐[34]krone‐10. Da der Hydrochinonring, über den dieser an C60 gebunden ist, ein π‐elektronenreicher Exodonor ist und daher mit der elektronenziehenden Fullerenkugel wechselwirkt, kommt es bei diesem ersten Fulleren‐Catenan zu einer bisher nicht erreichten intramolekularen Acceptor‐Donor‐Acceptor‐Donor‐Acceptor‐Stapelung

Gene delivery with polycationic fullerene hexakis-adducts

Polyplexes prepared from DNA and globular compact polycationic derivatives constructed around a fullerene hexakis-adduct core have shown remarkable gene delivery capabilities