Syntheses and biological evaluations of alpha-D-mannosyl [60]fullerenols.

[60]Fullerenols carrying mono- and bis-alpha-D-mannosyl linkages on the surface were prepared via a [3+2]-cycloaddition reaction between 2-azidoethyl alpha-D-mannoside and C(60) followed by polyhydroxylation with aqueous NaOH. Their biological activity was evaluated in terms of binding affinity to lectins by hemagglutination assay and surface plasmon resonance. [60]Fullerenols without the mannosyl linkage caused aggregation of erythrocytes and binding to a beta-D-galactopyranoside specific lectin (RCA(120)). In contrast, mono- and bis-mannosyl fullerenols were found to decrease the activity for both aggregating erythrocytes and binding to RCA(120), and mono-mannosyl fullerenols turned to binding to alpha-D-mannose specific lectin (Con A).