National Creative Research Initiative Center for Smart Supramolecules, Department of Chemistry and Division of Advanced Materials Science, Pohang University of Science and Technology (POSTECH), San 31 Hyoja-dong, Pohang 790-784, Republic of Korea.
Chemistry. 2010 Oct 25;16(40):12168-73. doi: 10.1002/chem.201001538.
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.
我们报告了由基于瓜环的甘露糖轮（ManCB[6]）在聚维酮（PV）上形成的糖假聚轮烷，它们不仅能有效诱导细菌聚集，而且对细菌与宿主细胞结合具有高抑制活性。我们制备并表征了三种糖假聚轮烷（1-3），它们在 PV 链上分别具有 10、5 和 3 个 ManCB[6]轮。细菌聚集实验和血凝抑制实验表明了糖假聚轮烷与 E. coli ORN178 之间的特异性和多价相互作用。化合物 3 特别有效地诱导细菌聚集，并且对 ORN178 诱导的血凝的抑制效力比单体甲基-α-甘露糖苷（Me-αMan）高 300 倍。此外，我们证明了它们对 ORN178 细菌黏附到尿路上皮细胞作为尿路感染模型的抑制活性。我们的研究结果表明，这些超分子碳水化合物簇在抗黏附治疗中具有潜在的用途。
