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Projeto de investigação
NMR Net - National Facility for Nuclear Magnetic Resonance: from Molecular Structure and Dynamics to Protein Function, Cell Physiology, and Metabolomics
Financiador
Autores
Publicações
Antimicrobial and cytotoxic activities of 1,2,3-triazole-sucrose derivatives
Publication . Petrova, Krasimira T.; Potewar, Taterao M.; Correia-da-Silva, Paula; Barros, M. Teresa; Calhelha, Ricardo C.; Ćirić, Ana; Soković, Marina; Ferreira, Isabel C.F.R.
A library of 1-(1′,2,3,3′,4,4′,6-hepta-O-acetyl-6′-deoxy-sucros-6′-yl)-1,2,3-triazoles have been investigated
for their antibacterial, antifungal and cytotoxic activities. Most of the target compounds showed
good inhibitory activity against a variety of clinically and food contaminant important microbial pathogens.
In particular, 1-(1′,2,3,3′,4,4′,6-hepta-O-acetyl-6′-deoxy-sucros-6′-yl)-4-(4-pentylphenyl)-1,2,3-
triazole (5) was highly active against all the tested bacteria with minimal inhibitory concentrations (MICs)
ranging between 1.1 and 4.4 μM and bactericidal concentrations (MBCs) from 2.2 and 8.4 μM. The compound
1-(1′,2,3,3′,4,4′,6-hepta-O-acetyl-6′-deoxy-sucros-6′-yl)-4-(4-bromophenyl)-1,2,3-triazole (3) showed
antifungal activity with MICs from 0.6 to 4.8 μM and minimal fungicidal concentrations (MFCs) ranging
between 1.2 and 8.9 μM. Furthermore, some of the compounds possessed moderate cytotoxicity against
human breast, lung, cervical and hepatocellular carcinoma cell lines, without showing toxicity for nontumor
liver cells. The above mentioned derivatives represent promising leads for the development of new
generation of sugar-triazole anti fungal agents.
Synthesis, characterization, antimicrobial and antitumor activities of sucrose Octa(N-ethyl)carbamate
Publication . Raposo, Claudia; Petrova, Krasimira T.; Barros, M. Teresa; Calhelha, Ricardo C.; Soković, Marina; Ferreira, Isabel C.F.R.
Sucrose octa(N-ethyl)carbamate was synthesized directly from sucrose and ethyl isocyanate,
and its structure was confirmed by various analytical methods, such as 1H and 13C NMR, FTIR,
m.p., MS, and optical rotation. Its antibacterial, antifungal and cytotoxic activities were investigated. It
exhibited strong inhibition against all bacteria tested, namely S. aureus (MIC 0.18±0.006), B. cereus
(MIC 0.094±0.000), M. flavus (MIC 0.28±0.01), L. monocytogenes (MIC 0.18±0.006), P. aeruginosa (MIC 0.094±0.002),
S. typhimurium (MIC 0.094±0.002), E. coli (MIC 0.18±0.006) and E. cloacae (MIC 0.18±0.006) and strong antifungal activity
towards T. viride (MIC 0.09 ± 0.006), A. versicolor (MIC 0.18 ± 0.01), A. ochraceus (MIC 0.375 ± 0.01) and P.
ochrochloron (MIC 0.375 ± 0.04). Furthermore, it showed moderate antitumor potential against human breast (GI50357.20±14.12), colon (GI50 332.43±11.19) and cervical (GI50 282.67±3.97) cell lines and, more important, without hepatotoxicity.
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Financiadores
Entidade financiadora
Fundação para a Ciência e a Tecnologia
Programa de financiamento
3599-PPCDT
Número da atribuição
RECI/BBB-BQB/0230/2012