Antimicrobial and cytotoxic activities of short carbon chain unsaturated sucrose esters
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A library of C3–C5 unsaturated 6-O-sucrose esters 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, 6-O-methacryloyl sucrose 2 and 1′,2,3,3′,4,4′,6′-hepta-O-acetyl-6-O-methacryloyl sucrose 9 were the most active bactericides against all the tested bacteria with minimal inhibitory concentrations (MICs) ranging between 0.24 and 1.40 μM. The compound 9 showed also the highest antifungal activity with MICs from 0.28 to 1.10 μM. The synthesized compounds possessed low cytotoxicity against human breast, lung, cervical, and hepatocellular carcinoma cell lines without showing toxicity for non-tumor liver cells. Thus, this library of short carbon chain unsaturated sucrose esters represent promising leads for the development of new generation of sucrose-based antimicrobial agents.
KeywordsUnsaturated esters Sucrose Antibacterial activity Antifungal activity Cytotoxic activity
This work has been supported by Fundação para a Ciência e a Tecnologia through grant nos. PEst-C/EQB/LA0006/2013 and PEst-OE/AGR/UI0690/2014. The authors thank Serbian Ministry of Education, Science, and Technological Development for financial support (grant number 173032).
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Conflict of interest
The authors declare that they have no competing interests.
- Abreu RMV, Ferreira ICFR, Calhelha RC, Lima RT, Vasconcelos MH, Adega F, Chaves R, Queiroz MJRP (2011) Anti-hepatocellular carcinoma activity using human HepG2 cells and hepatotoxicity of 6-substituted methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate derivatives: In vitro evaluation, cell cycle analysis and QSAR studies. Eur J Med Chem 46:5800–5806CrossRefPubMedGoogle Scholar
- Aguilar F, Charrondiere UR, Dusemund B, Galtier P, Gilbert J, Gott DM, Grilli S, Guertler R, Koenig J, Lambre C (2010) Scientific Opinion on the safety of sucrose esters of fatty acids prepared from vinyl esters of fatty acids and on the extension of use of sucrose esters of fatty acids in flavourings. EFSA J 8(3):1512–1548Google Scholar
- Avendaño C, Menéndez JC (2008) Medicinal chemistry of anticancer drugs. Elsevier, Amsterdam, OxfordGoogle Scholar
- Barros MT, Petrova KT, Correia-da-Silva P (2011) Sucrose chemistry: fast and efficient microwave-assisted protocols for the generation of sucrose-containing monomer libraries. In: Chandra U (ed) Microwave heating. InTech - Open Access Publisher, Rijeka, pp 309–332Google Scholar
- Clinical and Laboratory Standards Institute (2009) Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard, 8th edn. CLSI publication M07-A8. Clinical and Laboratory Standards Institute, Wayne, PAGoogle Scholar
- Peça IN, Petrova KT, Cardoso MM, Barros MT (2012) Preparation and characterization of polymeric nanoparticles composed of poly(DL-lactide-co-glycolide) and poly(DL-lactide-co-glycolide)-co-poly(ethylene glycol) 10%Triblock end-capped with a galactose moiety. React Funct Polym 72(10):729–735CrossRefGoogle Scholar
- Xin L (2014) Antimicrobial structure-efficacy relationship of sugar fatty acid esters. J Chem Pharm Res 6(5):944–946Google Scholar
- Xu JP (2016) Cancer inhibitors from Chinese natural medicines. CRC Press, Taylor & Francis GroupGoogle Scholar
- Ye R, Hayes DG, Burton R, Liu A, Harte FM, Wang Y (2016) Solvent-free lipase-catalyzed synthesis of technical-grade sugar esters and evaluation of their physicochemical and bioactive properties. Catalysts 6(78):1–13Google Scholar
- Ziemska J, Rajnisz A, Solecka J (2013) New perspectives on antibacterial drug research. Cent Eur J Biol 8(10):943–957Google Scholar