NMR Net - National Facility for Nuclear Magnetic Resonance: from Molecular Structure and Dynamics to Protein Function, Cell Physiology, and Metabolomics

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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.

2015Journal article

Open access

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.

2016Journal article

Open access