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).
Kato
H
H
Department of Chemistry, Nagoya University, Nagoya 464-8602, Japan.
Yashiro
A
A
Mizuno
A
A
Nishida
Y
Y
Kobayashi
K
K
Shinohara
H
H
D002244:Carbon / Q000737:chemistry* / Q000378:metabolism; D004903:Erythrocyte Aggregation; D004912:Erythrocytes / Q000378:metabolism; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000378:metabolism; D037741:Fullerenes; D006031:Glycosylation; D006386:Hemagglutination Tests; D037102:Lectins / Q000378:metabolism; D008358:Mannose / Q000138:chemical synthesis*; D011485:Protein Binding; D020349:Surface Plasmon Resonance / Q000379:methods
D016166:Free Radical Scavengers; D037741:Fullerenes; D037102:Lectins; C108127:fullerenol; D002244:Carbon; D008358:Mannose