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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


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 (međunarodna recenzija, članak, znanstveni)


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

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

Izvornik
Croatica chemica acta (0011-1643) 89 (2016), 2; 237-242

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

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

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija



POVEZANOST RADA


Projekt / tema
IP-2014-09-7899

Ustanove
Prirodoslovno-matematički fakultet, Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI


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