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Ultrasound-assisted catalyst-free thiol-yne click reaction in chitosan chemistry: Antibacterial and transfection activity of novel cationic chitosan derivatives and their based nanoparticles.
- Source :
-
International journal of biological macromolecules [Int J Biol Macromol] 2020 Jan 15; Vol. 143, pp. 143-152. Date of Electronic Publication: 2019 Dec 02. - Publication Year :
- 2020
-
Abstract
- In this work, we demonstrate that the thiol-yne click reaction could be efficiently mediated by ultrasonic irradiation and implement the ultrasound-assisted thiol-yne click reaction to chitosan chemistry as a polymer-analogous transformation. We optimize power and frequency of ultrasound to preserve selectivity of the click reaction and avoid ultrasonic degradation of the chitosan polymer chain. Thus, we obtain a new water-soluble betaine. Using ionic gelation of the obtained betaine derivatives of chitosan, we prepare nanoparticles with a unimodal size distribution. Furthermore, we present results of antibacterial and transfection activity tests for the chitosan derivatives and their based nanoparticles. The derivative with a medium molecular weight and a high degree of substitution demonstrated the best antibacterial effect. It derived nanoparticles with a size of ca. 100 nm and ΞΆ-potential of ca. +69 mV revealed even higher antibacterial activity, slightly superior to commercial antibiotics ampicillin and gentamicin. On the contrary, the obtained polymers possess a much more pronounced transfection activity as compared with their based nanoparticles and species with a low degree of substitution acts as the most efficient transfecting agent. Moreover, the obtained betaine chitosan derivatives as well as their derived nanoparticles are non-toxic.<br /> (Copyright © 2019 Elsevier B.V. All rights reserved.)
- Subjects :
- Anti-Bacterial Agents chemical synthesis
Catalysis
Cell Line
Cell Survival drug effects
Chemical Phenomena
Chemistry Techniques, Synthetic
Humans
Microbial Sensitivity Tests
Molecular Structure
Spectrum Analysis
Anti-Bacterial Agents chemistry
Anti-Bacterial Agents pharmacology
Cations chemistry
Chitosan chemistry
Click Chemistry
Nanoparticles chemistry
Sonication
Sulfhydryl Compounds chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1879-0003
- Volume :
- 143
- Database :
- MEDLINE
- Journal :
- International journal of biological macromolecules
- Publication Type :
- Academic Journal
- Accession number :
- 31805332
- Full Text :
- https://doi.org/10.1016/j.ijbiomac.2019.11.241