Comparative Study of Aryl O-, C-, and S-Mannopyranosides as Potential Adhesion Inhibitors toward Uropathogenic E. coli FimH

Mousavifar, Leila, Vergoten, Gérard, Charron, Guillaume et Roy, René (2019). Comparative Study of Aryl O-, C-, and S-Mannopyranosides as Potential Adhesion Inhibitors toward Uropathogenic E. coli FimH Molecules , vol. 24 , nº 3566. p. 1-12. DOI: 10.3390/molecules24193566.

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Résumé

A set of three mannopyranoside possessing identical 1,1'-biphenyl glycosidic pharmacophore but different aglyconic atoms were synthesized using either a palladium-catalyzed Heck cross coupling reaction or a metathesis reaction between their corresponding allylic glycoside derivatives. Their X-ray structures, together with their calculated 3D structures, showed strong indicators to explain the observed relative binding abilities against E. coli FimH as measured by a improved surface plasmon resonance (SPR) method. Amongst the O-, C-, and S-linked analogs, the C-linked analog showed the best ability to become a lead candidate as antagonist against uropathogenic E. coli with a Kd of 11.45 nM.

Type de document:	Article
Mots-clés libres:	D-mannosides; E. coli; FimH; Heck reaction; SPR; X-ray; carbohydrate; lectin; metathesis; uropathogenic infections
Centre:	Centre INRS-Institut Armand Frappier
Date de dépôt:	23 juill. 2021 17:14
Dernière modification:	23 juill. 2021 17:14
URI:	https://espace.inrs.ca/id/eprint/11643

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