Extracellular carbohydrate-protein interactions are critical in cellular communication processes such as fertilization, immune response, tumor cell metastasis, and bacterial or viral infection. Therefore, various types of carbohydrate clusters have been investigated to control the biological system by enhancing or inhibiting such interactions. Recently, we synthesized new carbohydrate clusters using cucurbit[6]uril (CB[6]) as a new multivalent scaffold, and demonstrated their specific and multivalent interactions with a lectin. Here we report pseudopolyrotaxanes (ManCB[6]@PV) formed by CB[6]-based mannose clusters (ManCB[6]) threaded on a polyviologen (PV) polymer to increase the multivalent effects. Mannose units on the glyco-pseudopolyrotaxane selectively bind to the FimH proteins on the ORN 178 E. coli strain and thus efficiently agglutinates the bacteria. The ability of ManCB[6]@PV to inhibit ORN 178 bacterial binding to UROtsa cell (urinary epithelial cell) was investigated in vitro by flow cytometry. In the absence of the ManCB[6]@PV, the FITC-labeled ORN178 significantly interact with the UROtsa cell and thus give strong fluorescence signal. However, after pre-treating of ManCB[6]@PV to the ORN 178, the fluorescence signal was reduced by inhibiting the binding between FITC-labeled bacteria and the UROtsa cells. The results suggest glyco-pseudopolyrotaxanes are potentially useful in antiadhesion therapy by inhibiting infection of pathogens into the host cell.

Cucurbituril-based glyco-pseudopolyrotaxanes and their inhibitory activity for bacterial adhesion

239th National Meeting (2010)

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