Sulfonated, sulfated thioglycosides and multivalence in heparanase inhibition

-linked disaccharides, demonstrating their potential as heparanase inhibitors. In this article, we introduced a sulfonate moiety as a stable analog of the sulfate group. Comparative heparanase inhibition assays reveal that sulfated disaccharides exhibit significantly greater activity than their sulfonated counterparts. Furthermore, multivalent glycoclusters were prepared by coupling sulfated thiodisaccharides to maltotriose and cyclodextrin scaffolds, providing novel molecular architectures that show promising heparanase inhibition.