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CuAAC synthesis of resorcin[4]arene-based glycoclusters as multivalent ligands of lectins

2011; Royal Society of Chemistry; Volume: 9; Issue: 19 Linguagem: Inglês

10.1039/c1ob05676j

1477-0539

Zahid Soomro, Samy Cecioni, Helen Blanchard, Jean‐Pierre Praly, Anne Imberty, Sébastien Vidal, Susan E. Matthews,

Monoclonal and Polyclonal Antibodies Research

Synthetic multivalent glycoclusters show promise as anti-adhesives for the treatment of bacterial infections. Here we report the synthesis of a family of tetravalent galactose and lactose functionalised macrocycles based on the resorcin[4]arene core. The development of diastereoselective synthetic routes for the formation of lower-rim propargylated resorcin[4]arenes and their functionalistion via Cu-catalyzed azide–alkyne click chemistry is described. ELLA binding studies confirm that galactose sugar clusters are effective ligands for the PA-IL bacterial lectin of Pseudomonas aeruginosa while poor binding for the lactose-based monovalent probe and no binding could be measured for the multivalent glycoclusters was observed for the human galectin-1.