Modular synthesis of silicon (IV) phthalocyanine conjugates bearing glycosylated axial ligands

Abstract

Phthalocyanines (Pcs) are near-infrared photosensitizers with therapeutic potential for the treatment of bacterial infections and cancer. However, their clinical utility has been hindered by poor solubility in biological fluids, lack of specificity, and limited clearance from affected tissues. Glycosylated Pcs have the potential to overcome these issues by providing increased solubility and tumor specific targeting. However, reliable methods for their synthesis remains challenging. Here we present our first approach towards the synthesis of a series of silicon (IV) phthalocyanine conjugates bearing axial carbohydrate ligands (CPcCs). The novelty of our approach lies in the installation of axial alkyne ligands which can be functionalized with readily accessible acetyl protected azido glycosides, thus providing a modular approach for the synthesis of these complex macromolecules.