New Glycoconjugation Synthetic Approaches for Therapeutic and Diagnostic Applications

Glycoconjugation is currently a very investigated and applied procedure in the field of synthetic chemistry and clinical research and it has a key role in carbohydrate-based drugs and vaccines design. In the chemotherapy field it leads to molecules with therapeutic or diagnostic action mostly directed towards cancer cells, in consideration of an enhanced selectivity. In this context, the present PhD thesis reports the stereoselective derivatization of therapeutic and/or diagnostic agents with carbohydrates, and the synthesis of new glycomimetics as potential bioactive compounds. In particular, the connection of carbohydrate-based ligands to antiproliferative Ruthenium(II)-arene complexes and diiron bis(cyclopentadienyl) complexes is extensively studied. The glycoconjugation approach was also used for the development of specific diagnostic agents, able to detect the increased level and activity that hydrolytic enzymes, such as α- and β-glucosidases show in presence of tumor pathology. In addition, this thesis, also reports the synthesis of new interesting glyco-mimetics as potential antiviral agents and the development of a new completely stereoselective intramolecular version of a O-glycosylation process for the construction of polycyclic systems containing pyran-dioxane moieties.