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- W2912476614 endingPage "757" @default.
- W2912476614 startingPage "749" @default.
- W2912476614 abstract "Antimicrobial resistance has become a serious concern for the treatment of urinary tract infections. In this context, an anti-adhesive approach targeting FimH, a bacterial lectin enabling the attachment of E. coli to host cells, has attracted considerable interest. FimH can adopt a low/medium-affinity state in the absence and a high-affinity state in the presence of shear forces. Until recently, mostly the high-affinity state has been investigated, despite the fact that a therapeutic antagonist should bind predominantly to the low-affinity state. In this communication, we demonstrate that fluorination of biphenyl α-d-mannosides leads to compounds with perfect π-π stacking interactions with the tyrosine gate of FimH, yielding low nanomolar to sub-nanomolar KD values for the low- and high-affinity states, respectively. The face-to-face alignment of the perfluorinated biphenyl group of FimH ligands and Tyr48 was confirmed by crystal structures as well as 1 H,15 N-HSQC NMR analysis. Finally, fluorination improves pharmacokinetic parameters predictive for oral availability." @default.
- W2912476614 created "2019-02-21" @default.
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- W2912476614 creator A5043448626 @default.
- W2912476614 date "2019-04-03" @default.
- W2912476614 modified "2023-10-01" @default.
- W2912476614 title "Improvement of Aglycone pi-Stacking Yields Nanomolar to Sub-nanomolar FimH Antagonists." @default.
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