Synthesis of new class of fucoside and mannoside homo glycodendrimers multivalent targeted ligands.

Source: PubMed, NCBI / U.S. National Library of Medicine

Glycodendrimers are emerging as a novel therapeutic for treating various diseases, providing a safe and efficient carriers for drug delivery due to the combined multivalent cooperativity of dendrimers with targeted ligands. In this article, we describe a modular synthetic methodology to generate libraries of a dual functional glycodendrimer containing glucuronic ester residue equipped with targeting ligands. The ester group can be selectively unmasked by acid treatment, allowing the conjugation of the desired antibiotics to the glycodendrimer. The methodology was applied to prepare a new class of tri- and hexavalent glycodendrimers that differs in the linking functionality of the ligand moiety. The glycodendrimers are composed of three major moieties: dendrimer core, prodrug scaffold, and lectin-targeting carbohydrate. The key buildup of complexity was accomplished via a double-stage convergent approach using copper(I) mediated azide-alkyne cycloaddition (CuAAC). We believe the design of this glycodendrimer would offer more effective treatment by delivering such antibiotics directly to the infected cells, allowing it to precisely target and eliminate the infection. It is to be anticipated that other biologically important complex glycodendrimers can be prepared using the strategic techniques employed for the synthesis of the target dendrimers in this study.