A Fullerene-Based Selenosugar Ball

Fullerenes functionalized with selenosugar moieties are of particular interest because of their important properties, as one fragment enhances the properties of the other. Selenosugars are not only solubilizing groups, but their intrinsic biological properties also provide additional attractive features to the conjugates. Here the synthesis is reported of a fullerene hexakis-adduct decorated with 12 peripheral seleno-D-talitol moieties with a Th-symmetric structure, which can be efficiently synthesized from the hexakisadduct of [60]fullerene prepared via a cycloaddition reaction and subsequent copper-catalyzed azide-alkyne cycloaddition click chemistry. This large-scale system, refer to as the selenosugar ball (SeB), has been characterized by 1HNMR and 13C NMR spectroscopy, mass spectrometry, UV-spectroscopy, and dynamic light scattering (DLS). Theoretical calculations using the multilevel DFTB3LYP- D3(BJ)/6–311 G(2 d,p)//PM7 methodology are performed to predict the most stable conformation for the compound and to determine the factors that control the geometry of this molecule. In addition, some physicochemical parameters are estimated. Also, this new compound is tested on human keratinocyte HaCaT cells to determine its cytotoxicity and potential applications.