Synthesis of tetraphenylethylene based glycoclusters

Emerging evidence exists that carbohydrate-lectin interactions are fundamental for mediating numerous cellular processes including cellular communication, signalling, and recognition. However, several carbohydrate-lectin interactions have been linked to various diseases including cancer. Designing carbohydrate-lectin inhibitors has been a target for potent inhibitors to such diseases1. The tetraphenylethylene (TPE) based glycoclusters has shown promising developments as potent inhibitors for selected galectins in recent years, particularly within the Murphy group2,3. Therefore, the aim of my research project is to enhance the groundwork established within the Murphy group by exploring the TPE based glycoclusters of higher valences than previously investigated. This includes hexavalent TPE derivatives by linking two trivalent TPE scaffolds together with a PEG (polyethylene glycol), essentially forming a dimer. This homodimerization process involves connecting two identical molecules together to from a single molecule, which can induce synergistic effects resulting in greater potency than the sum of their individual effect4. The synthesis of tetraphenyl ethylene glycoclusters with varying multivalency has been successfully achieved, opening new avenues in the study of carbohydrate-protein interactions and multivalent binding systems. TPE glycoclusters exhibit exceptional properties, including fluorescence and robust structural stability and enhancing binding affinity making them highly promising avenues for success.

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University of Galway

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Attribution-NonCommercial-NoDerivatives 4.0 International

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University of Galway Theses (Research Masters Theses)