Glyco‐pseudopolyrotaxanes: Carbohydrate Wheels Threaded on a Polymer String and Their Inhibition of Bacterial Adhesion

We report glyco‐pseudopolyrotaxanes composed of cucurbit[6]uril‐based mannose wheels (ManCB[6]) threaded on polyviologen (PV), which not only effectively induce bacterial aggregation, but also exhibit high inhibitory activity against bacterial binding to host cells. Three glyco‐pseudopolyrotaxanes ( 1 – 3 ), which have 10, 5, and 3 ManCB[6] wheels, respectively, on a PV string, were prepared and characterized. Bacterial aggregation assays and hemagglutination inhibition assays illustrated the specific and multivalent interaction between the glyco‐pseudopolyrotaxanes and E. coli ORN178. Compound 3 was especially effective at inducing bacterial aggregation and showed 300 times higher inhibitory potency than monomeric methyl‐α‐mannoside (Me‐αMan) for ORN178‐induced hemagglutination. Furthermore, we demonstrated their inhibitory activities for the adhesion of ORN178 bacteria to urinary epithelial cells as a model of urinary tract infection. Our findings suggest that these supramolecular carbohydrate clusters are potentially useful in antiadhesion therapy.