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Synthesis of novel 1H-tetrazole derivatives of chitosan via metal-catalyzed 1,3-dipolar cycloaddition. Catalytic and antibacterial properties of [3-(1H-tetrazole-5-yl)ethyl]chitosan and its nanoparticles.
- Source :
-
International journal of biological macromolecules [Int J Biol Macromol] 2019 Jul 01; Vol. 132, pp. 340-350. Date of Electronic Publication: 2019 Mar 26. - Publication Year :
- 2019
-
Abstract
- New tetrazole derivatives of chitosan with low, moderate, and high degrees of substitution were obtained using a novel approach, i.e. metal-catalyzed 1,3-dipolar cycloaddition of azide ion to cyanoethyl chitosan in water - the most straightforward, selective and preparatively convenient route to tetrazole chitosan derivatives. Ionic gelation of these tetrazole derivatives with sodium tripolyphosphate resulted in nanoparticles with an apparent hydrodynamic diameter of 100-800 nm and ζ-potential of 22-57 mV. The tetrazole derivatives of chitosan and their nanoparticles were tested as catalysts of the aldol reaction between p-chlorobenzaldehyde and acetone. The tetrazole derivatives have been found to possess better catalytic properties than the corresponding nanoparticles. The obtained data indicate that the tetrazole-chitosan polymers exhibit high catalytic activity in aldol reaction, and these catalysts are among the best studied so far. Tetrazole derivatives and their nanoparticles were also tested as antibacterial agents. The in vitro antibacterial activity against S. aureus and E. coli of the tetrazole-chitosan-based nanoparticles is much more than the activity of the corresponding tetrazole-chitosan polymers, and their activity is comparable with that of antibiotics ampicillin and gentamicin.<br /> (Copyright © 2019. Published by Elsevier B.V.)
- Subjects :
- Anti-Bacterial Agents chemistry
Azides chemistry
Catalysis
Chitosan chemistry
Cycloaddition Reaction
Escherichia coli drug effects
Nitriles chemistry
Staphylococcus aureus drug effects
Anti-Bacterial Agents chemical synthesis
Anti-Bacterial Agents pharmacology
Chitosan chemical synthesis
Chitosan pharmacology
Metals chemistry
Nanoparticles chemistry
Tetrazoles chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1879-0003
- Volume :
- 132
- Database :
- MEDLINE
- Journal :
- International journal of biological macromolecules
- Publication Type :
- Academic Journal
- Accession number :
- 30922911
- Full Text :
- https://doi.org/10.1016/j.ijbiomac.2019.03.153