Synthesis and biological testing of thioalkane- and thioarene-spaced bis-β-d-glucopyranosides

A three-step synthesis of bis-β-d-glucopyranosides containing thioalkane or thioarene spacers of different length and flexibility is described. The key-step reaction allows an easy modulation of final saccharidic products so that a library of molecules with different glycosidic residues and spacers can be obtained. Two of the new thioarene-spaced bis-β-d-glucopyranosides endow with a specific cytotoxic potential. A more detailed investigation of one of the two compounds ascertains that this effect is attributable to induction of cell death by apoptosis.

A series of thio-bis-β-d-glucopyranosides containing alkane or arene spacers of different length and flexibility have been synthesized. The relationship between their molecular structure and biological response has been investigated. Product shown below proved to be a good inductor of cell death by apoptosis.Figure optionsDownload as PowerPoint slide