Poly(amido amine)-Based Mannose-Glycodendrimers As Multielectron Redox Probes for Improving Lectin Sensing

Abstract

An easy-to-prepare series of electroactive PAMAM-based dendrimers of generations G0 to G2 having mannopyranosylferrocenyl moieties in the periphery to detect carbohydrate-protein interactions is reported. The synthesis involved the functionalization of the PAMAM surface with azidomethylferrocenyl groups and subsequent coupling of mannoside units by Cu(I)-catalyzed Huisgen reaction. The binding affinity of the series of electroactive glycodendrimers was studied by isothermal titration calorimetry (ITC) and differential pulse voltammetry (DPV). Upon complexation of the glycodendrimers conjugates with prototypical concanavalin A (Con A), voltammograms showed a decrease of the peak current. Such dendrimers showed a notable improvement of redox sensing abilities towards Con A when compared with mono- and divalent analogues, based on both the glycoside multivalent and ferrocene dendritic effects.