Dynamic multivalent interaction of phenylboronic acid functionalized dendrimers with vesicles

Over the past decade cyclodextrin vesicles were established as a versatile model for biological membranes since they can be easily modified with functional groups due to the spontaneous formation of host-guest complexes. In this article we report the interaction of phenylboronic acid functionalized polyamidoamine (PAMAM) dendrimers and cyclodextrin vesicles decorated with a catechol-adamantane conjugate to investigate dynamic multivalent recognition processes on membrane surfaces. The orthogonality and the multivalency in the ternary system of host vesicle, guest catechol conjugate and functionalized dendrimers were studied by isothermal titration calorimetry (ITC), dynamic light scattering (DLS) and time-depended measurements of optical density at 400 nm (OD400). It was shown that the aggregation of vesicles is highly dependent on the concentration of boronic acids as well as the generation, i.e. valency, of the dendrimers.