engleski

Ferrocene conjugates with mannose : synthesis and influence of ferrocene aglycon on mannose-mediated adhesion of Escherichia coli

Bacterial adhesion, mediated through interaction of bacterial lectins with carbohydrate structures presented on the surface of the host cells, is a prerequisite for infection. Anti-adhesion therapy, based on the inhibition of lectins by suitable carbohydrates, has been considered as a weapon for the combat of microbial diseases. Structural alteration of aglycon portions of mannose derivatives strongly influences their inhibitory potency toward type 1 fimbriated Escherichia coli. Thus several conjugates of mannosecontaining ferrocene aglycon moieties were synthesized and tested. The novel ferrocene conjugates 10, 12 and 14 were obtained by esterification of O-mannosylated propionic acid 1 with ferrocene alcohols R-Fn-(CH2)n-OH (Fn = 1, 1’-ferrocenylene ; 2, n=1, R =COOMe ; 7, n = 1, R =NHBoc ; 8, n = 2, R =H) in the presence of Boc2O/DMAP with subsequent debenzylation of the intermediate O-protected esters. Performed hemagglutination inhibitory tests showed that the examined bioorganometallics exhibit better inhibitory activity than known inhibitor methyl a-D-mannoside. Thus ferrocene–mannose conjugate 14 with the dimethylene spacer between ferrocene core and chiral linker displayed the best inhibitory efficiency.

ferrocene; mannose; E. coli; type 1 fimbriae; hemagglutination

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