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.
Kim
Jeeyeon
J
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.
Ahn
Youngjoo
Y
Park
Kyeng Min
KM
Lee
Don-Wook
DW
Kim
Kimoon
K
D001422:Bacterial Adhesion / Q000187:drug effects*; D001952:Bridged-Ring Compounds / Q000737:chemistry* / Q000494:pharmacology; D002241:Carbohydrates / Q000737:chemistry* / Q000494:pharmacology*; D003505:Cyclodextrins / Q000737:chemistry* / Q000494:pharmacology*; D004847:Epithelial Cells / Q000187:drug effects*; D006384:Hemagglutination / Q000187:drug effects*; D007093:Imidazoles / Q000737:chemistry* / Q000494:pharmacology; D008358:Mannose / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D020442:Poloxamer / Q000737:chemistry* / Q000494:pharmacology*; D011108:Polymers / Q000737:chemistry* / Q000494:pharmacology*; D043862:Rotaxanes / Q000737:chemistry* / Q000494:pharmacology*; D014552:Urinary Tract Infections / Q000188:drug therapy; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils
D001952:Bridged-Ring Compounds; D002241:Carbohydrates; D003505:Cyclodextrins; D007093:Imidazoles; D008358:Mannose; D020442:Poloxamer; D011108:Polymers; D043862:Rotaxanes; C475674:pseudopolyrotaxane; C454805:cucurbit(6)uril; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils