Antimicrobial and cytotoxic activities of 1,2,3-triazole-sucrose derivatives

• Published in: Carbohydrate research Vol. 417; pp. 66 - 71
• Main Authors: Petrova, Krasimira T., Potewar, Taterao M., Correia-da-Silva, Paula, Barros, M. Teresa, Calhelha, Ricardo C., Ćiric, Ana, Soković, Marina, Ferreira, Isabel C.F.R.
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier Ltd 19.11.2015
• Subjects: 1,2,3-Triazoles; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - pharmacology; Antibacterial activity; Antifungal activity; Antifungal Agents - chemical synthesis; Antifungal Agents - pharmacology; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - pharmacology; Cell Line, Tumor; Cell Survival - drug effects; Cytotoxic activity; Dose-Response Relationship, Drug; Female; Gram-Negative Bacteria - drug effects; Gram-Negative Bacteria - growth & development; Gram-Positive Bacteria - drug effects; Gram-Positive Bacteria - growth & development; Hepatocytes - cytology; Hepatocytes - drug effects; Humans; Microbial Sensitivity Tests; Mitosporic Fungi - drug effects; Mitosporic Fungi - growth & development; Organ Specificity; Primary Cell Culture; Species Specificity; Structure-Activity Relationship; Sucrose; Sucrose - analogs & derivatives; Sucrose - chemical synthesis; Sucrose - pharmacology; Triazoles - chemical synthesis; Triazoles - pharmacology; 1,2,3-Triazoles; Antifungal activity; Antibacterial activity; Sucrose; Cytotoxic activity
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2015.09.003

•A library of sucrose 1,2,3-triazoles has been screened for their biological activities.•Their antibacterial, antifungal and cytotoxic activities were tested.•4-Pentylphenyl triazole derivative had the highest antibacterial activity.•4-Bromophenyl triazole derivative was the strongest antifungal agent.•The compounds showed moderate cytotoxic potential without hepatotoxicity. 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 non-tumor liver cells. The above mentioned derivatives represent promising leads for the development of new generation of sugar-triazole antifungal agents.