Functionalizing the glycocalyx of living cells with supramolecular guest ligands for cucurbit[8]uril-mediated assembly

Abstract

Multiple naphthol ligands were installed on the glycocalyx of white blood cells via metabolic labeling and subsequent strain promoted azide-alkyne cycloaddition. Only when cucurbit[8]uril was present to drive the formation of ternary complexes, cells specifically assembled on a methylviologen functionalized supported lipid bilayer through multivalent interactions.

Dynamic supramolecular polymers built from cucurbit[n]urils and viologens

“…have successfully used CB[8] hosts to immobilize blood cells on a methyl viologen (MV) functionalized supported lipid bilayer. Cells have been found to specifically assemble on the bilayer through multivalent interactions only when CB[8] is present to drive the formation of ternary complexes . Supramolecular assemblies between CB[ n ]s and viologens have also found interesting application in the fields of biomaterials and nano‐medicine.…”

Cucurbituril As A Versatile Tool to Tune the Functions of Proteins

“…Cucurbiturils are a series of supramolecular macrocyclic hosts with n glycoluril bridged by 2n methylenes, yielding cucurbituril series (CB [5,6,7,8,10,13,14,15]). CB [5][6][7][8][9][10] (except for CB [13][14][15]) share a common pumpkin-shaped structure with a large hydrophobic cavity and two negatively charged portals.…”

“…[14][15][16][17][18][19] For example, activity changes could be found both in CB [8]induced FGG-cap-9 dimer [18] (compared with FGG-cap-9 monomer) and CB [8]-induced split-luciferase complementation [19] (compared with split fragments). [14][15][16][17][18][19] For example, activity changes could be found both in CB [8]induced FGG-cap-9 dimer [18] (compared with FGG-cap-9 monomer) and CB [8]-induced split-luciferase complementation [19] (compared with split fragments).…”

Stimuli‐Responsive Cucurbit[n]uril‐Mediated Host‐Guest Complexes on Surfaces

“…[95] As an alternative to integrin-receptor mediated adhesion of cells on CB [8] SAMs, we have recently metabolically expressed naphthol moieties on the outer surface of non-adherent Jurkat cells (Figure 11c). [93] Specific host-guest was demonstrated on surfaces and the method potentially allows for programmable supramolecular interactions with spatial and temporal control over cell adhesion as well.…”

“…[67] We have reported successful ways to anchor proteins, viruses, bacteria and cells using CB[n]-mediated complexation on SAMs. [73,74,[88][89][90][91][92][93][94][95][96][97] A focus point has been to employ siteselectively guest-labeled proteins, which can be used for oriented positioning of proteins, as for example demonstrated on CB [7] SAMs. Mono-and divalent ferrocenylated yellow fluorescent protein were prepared and these formed stable inclusion complexes on CB [7] SAMs (method Figure 5b).…”