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Comparison of inhibitory activities of meta and para substituted N-aryl 3-hydroxypyridin-4-one mannosides towards type 1 fimbriated E. coli (CROSBI ID 228960)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Petrović Peroković, Vesna ; Ribić, Rosana ; Car, Željka ; Tomić, Srđanka Comparison of inhibitory activities of meta and para substituted N-aryl 3-hydroxypyridin-4-one mannosides towards type 1 fimbriated E. coli // Croatica chemica acta, 89 (2016), 2; 237-242. doi: 10.5562/cca2890

Podaci o odgovornosti

Petrović Peroković, Vesna ; Ribić, Rosana ; Car, Željka ; Tomić, Srđanka

engleski

Comparison of inhibitory activities of meta and para substituted N-aryl 3-hydroxypyridin-4-one mannosides towards type 1 fimbriated E. coli

In uropathogenic Escherichia coli, mannose- specific adhesion is mediated by the FimH adhesin located at the tip of type 1 fimbriae. Novel mannosylated N-aryl-substituted 3- hydroxypyridin-4-ones with meta substituents on the aryl part of the molecule were prepared, and their inhibitory properties towards the adhesion of E. coli to guinea pig erythrocytes explored using the hemagglutination assay. These results were compared with inhibitory potencies of analogous para derivatives. The assays revealed greater preference of FimH towards para substituted compounds in general, with p-nitro and p-methoxy substituted substrates being much more effective then the hydrophobic p-methyl compound. When substituents are in meta position the positive affect on the binding of compounds in the FimH binding site was observed with all compounds tested but the structure with an alkyl group was shown to be the most effective one. This study provides guidelines for the rational design of novel, more effective series of FimH antagonists.

N-aryl 3-hydroxypyridin-4-one mannosides ; FimH antagonist ; hemagglutination ; E. coli

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Podaci o izdanju

89 (2)

2016.

237-242

objavljeno

0011-1643

10.5562/cca2890

Povezanost rada

Kemija, Biologija

Poveznice