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

Bioorg Med Chem Lett. 2001 Nov 19;11(22):2935-9. doi: 10.1016/s0960-894x(01)00583-2.

Abstract

[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).

MeSH terms

  • Carbon / chemistry*
  • Carbon / metabolism
  • Erythrocyte Aggregation
  • Erythrocytes / metabolism
  • Free Radical Scavengers / chemical synthesis*
  • Free Radical Scavengers / metabolism
  • Fullerenes*
  • Glycosylation
  • Hemagglutination Tests
  • Lectins / metabolism
  • Mannose / chemical synthesis*
  • Protein Binding
  • Surface Plasmon Resonance / methods

Substances

  • Free Radical Scavengers
  • Fullerenes
  • Lectins
  • fullerenol
  • Carbon
  • Mannose