Titill: | Chitosan-hydroxycinnamic acid conjugates: Optimization of the synthesis and investigation of the structure activity relationship |
Höfundur: |
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Útgáfa: | 2022-02 |
Tungumál: | Enska |
Umfang: | 118896 |
Háskóli/Stofnun: | Háskóli Íslands University of Iceland |
Svið: | Heilbrigðisvísindasvið (HÍ) School of Health Sciences (UI) |
Deild: | Lyfjafræðideild (HÍ) Faculty of Pharmaceutical Sciences (UI) |
Birtist í: | Carbohydrate Polymers;277(118896) |
ISSN: | 0144-8617 |
DOI: | https://doi.org/10.1016/j.carbpol.2021.118896 |
Efnisorð: | Chitosan; Antioxidant; Antibacterial; Chemical modification; Protection groups; Design of Experiment (DOE); Kítósan; Andoxunarefni; Lyfjafræði |
URI: | https://hdl.handle.net/20.500.11815/3997 |
Tilvitnun:Nagy, V., Sahariah, P., Hjálmarsdóttir, M. Á., Másson, M. (2022). Chitosan-hydroxycinnamic acid conjugates: Optimization of the synthesis and investigation of the structure activity relationship. Carbohydrate Polymers, 277, 118896. https://doi.org/10.1016/j.carbpol.2021.118896
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Útdráttur:A new synthesis method was developed and optimized by a full factorial design for conjugating hydroxycinnamic
acids (HCA-s) to chitosan. Cinnamic acid and tert-butyldimethylsilyl protected HCA-s were converted to their
corresponding acyl chlorides and reacted with 3,6-di-O-tert-butyldimethylsilyl-chitosan to selectively form amide
linkages, resulting in water-soluble conjugates after deprotection. Nineteen conjugates were obtained with
various degrees of substitution (DS) ranging from 3% to 60%. The conjugates were found to be bactericidal
against Staphylococcus aureus and Escherichia coli, with their activities equal to chitosan at low DS but an increase
in the DS correlated with reduced activity. DPPH (2,2-diphenyl-1-picrylhydrazyl) scavenging assay was performed to determine the EC50 values. Chitosan only exhibited low antioxidant activity, whereas the HCAchitosan conjugates exhibited higher antioxidant activities correlating with the DS. One caffeic acid conjugate
(21%) was 4000 times more active than chitosan and more active than free caffeic acid.
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