Sulfated glycofuranans as inhibitors of melanoma lung metastasis

Abstract

Chemically synthesized (1 → 5)-β-D-glucofuranan, (1 → 5)-β-D-galactofuranan, (1 → 5)-β-D-xylofuranan, (1 → 5)-α-L-arabinofuranan, natural xylan, and curdlan were sulfated to investigate their inhibitory activities on B16-BL6 lung metastasis and anticoagulant activities. (1 → 5)-β-D-Glucofuranan sulfate, (1 → 5)-β-D-galactofuranan sulfate, xylan sulfate, and curdlan sulfate had binding abilities with B16-BL6 melanoma lysate. The inhibitory activities of sulfated polysaccharides on B16-BL6 lung metastasis selected by heparin binding assay were in the order (1 → 5)-β-D-galactofuranan sulfate > (1 → 5)-β-D-glucofuranan sulfate > xylan sulfate >> curdlan sulfate. Furthermore, (1 → 5)-β-D-galactofuranan sulfate, (1 → 5)-β-D-glucofuranan sulfate, and xylan sulfate had not only high inhibitory activity on B16-BL6 lung metastasis but also low anticoagulant activity. The correlation between chemical structure and biological activity is discussed.