Naslov
Synthesis, spectral characterization and inhibitory potency of ferrocene-containing mannosides toward type 1 fimbriated Escherichia coli

Autori
Kovač, Veronika ; Ribić, Rosana ; Petrović Peroković, Vesna ; Tomić Pisarović, Srđanka ; Barišić, Lidija

Izvornik
Applied organometallic chemistry (0268-2605) 30 (2016), 7; 524-530

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

Ključne riječi
Ferrocene ; Mannose ; E. coli ; Type 1 fimbriae ; Hemagglutination

Sažetak
E. coli adhesion to the bladder epithelium is mediated through recognition of the tissue-surface mannosylated proteins with bacterial lectin FimH. The inhibition of this recognition-dependent interaction has been recognized as a promising strategy for the development of an anti-adhesion therapy. The mannosides with either aryl- or elongated alkyl-functionalized aglycon portions have been shown to be potent inhibitors of FimH-mediated adhesion. Thus, we have synthesized four mannose-based bioorganometallics containing an extended alkyl chain between sugar and ferrocene components connected via ester [14 (n = 4), 15 (n = 5)] or amide linkage [18 (n = 3) and 19 (n = 4)]. The novel bioconjugates were characterized using IR and NMR (1H, 13C, COSY, NOESY, HSQC, HMBC) spectroscopy, ESI-MS and HRMS. The hemagglutination inhibitory assay of the novel bioorganometallics revealed an enhanced inhibitory potential in comparison to methyl alpha-D-mannoside. Thereby, the bioconjugate 19 exibited a 2-fold increase in inhibitory activity compared with 14, 15 and 18.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA