Supramolecular chemistry resembles the dynamicity and reversibility of natural biological systems. Yet, its artificial and tunable character is a powerful tool to control spatial (and temporal) organization of biological systems. Cucurbit[8]uril (CB8) is an artificial receptor big enough to handcuff in its cavity two guest molecules, such as the electron-poor methylviologen and the electron-rich naphthol. When these guests are opportunely modified, CB8 can act as a “glue” between cells and materials and enable the control over cell adhesion. To this end, a biomimetic and non-fouling material such as lipid bilayers and a non-adherent cell line (Jurkat cells) were engineered to selectively interact and control the immobilization of the cells on a supported lipid bilayer. A number of naphthol moieties were artificially displayed on the outer layer of the cell membrane. At first an azide was introduced on the cell glycocalyx via metabolic labeling (1) and subsequently bio-orthogonally reacted with a strained octyne (2) bearing a naphthol group. On the other side, the supported lipid bilayer was functionalized with methylviologen. Finally, the supramolecular control over cell/surface interaction was enabled by CB8, which selectively triggered the cell adhesion on the lipid bilayer. 1) S.T. Laughlin, C.R. Bertozzi, 2007 Nature protocols, 2, 11, 2930-2944 2) J. Dommerholt, et al., 2010 Angewandte Chemie - International Edition, 49, 9422-9425

Supramolecular control of cell adhesion via cucurbit[8]uril on supported lipid bilayer

251st National Meeting (2016)

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