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


Kovačević, Monika; Barišić, Lidija; Ribić, Rosana; Petrović Peroković, Vesna; Tomić, Srđanka; Rapić, Vladimir
Ferrocene conjugates with mannose : synthesis and influence of ferrocene aglycon on mannose-mediated adhesion of Escherichia coli // Applied organometallic chemistry, 26 (2012), 2; 74-79 doi:10.1002/aoc.1869 (međunarodna recenzija, članak, znanstveni)


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

Autori
Kovačević, Monika ; Barišić, Lidija ; Ribić, Rosana ; Petrović Peroković, Vesna ; Tomić, Srđanka ; Rapić, Vladimir

Izvornik
Applied organometallic chemistry (0268-2605) 26 (2012), 2; 74-79

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

Ključne riječi
Ferrocene; mannose; E. coli; type 1 fimbriae; hemagglutination

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
058-1191344-3122 - Metalocenski biokonjugati, heterocikli i makromolekule (Veronika Kovač, )
119-1191344-3121 - Sinteze i enzimske transformacije biološki aktivnih spojeva (Srđanka Tomić-Pisarović, )

Ustanove
Prehrambeno-biotehnološki fakultet, Zagreb,
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
  • Scopus


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