Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 40, Pages 12168-12173Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201001538
Keywords
carbohydrates; cluster compounds; cucurbiturils; host-guest systems; rotaxanes; supramolecular chemistry
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Funding
- Korean Ministry of Education, Science and Technology [R31-2008-000-10059-0]
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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-alpha-mannoside (Me-alpha Man) 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.
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