Thiolated methylated dimethylaminobenzyl chitosan: A novel chitosan derivative as a potential delivery vehicle

Chitosan is a natural mucoadhesive, biodegradable, biocompatible and nontoxic polymer which has been used in pharmaceutical industry for a lot of purposes such as dissolution enhancing, absorption enhancing, sustained releasing and protein, gene or drug delivery. Two major disadvantages of chitosan...

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Bibliographic Details
Published in:International journal of biological macromolecules 2017-02, Vol.95, p.574-581
Main Authors: Hakimi, Shirin, Mortazavian, Elaheh, Mohammadi, Zohreh, Samadi, Fatemeh Yazdi, Samadikhah, Hamidreza, Taheritarigh, Sadegh, Tehrani, Niyousha Rafiee, Rafiee-Tehrani, Morteza
Format: Article
Language:English
Subjects:
Cell Survival - drug effects
Chitosan - analogs & derivatives
Chitosan - chemistry
Chitosan - toxicity
Cytotoxicity
Drug Carriers - chemistry
Drug Carriers - toxicity
HEK293 Cells
Humans
New chitosan derivative
Solubility
Sulfhydryl Compounds - chemistry
Sulfhydryl Compounds - toxicity
Synthesis
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Summary:Chitosan is a natural mucoadhesive, biodegradable, biocompatible and nontoxic polymer which has been used in pharmaceutical industry for a lot of purposes such as dissolution enhancing, absorption enhancing, sustained releasing and protein, gene or drug delivery. Two major disadvantages of chitosan are poor solubility in physiological pH and low efficiency for protein and gene delivery. In this study thiolated methylated N-(4-N,N-dimethylaminobenzyl) chitosan was prepared for the first time in order to improve the solubility and delivery properties of chitosan. This novel chitosan derivative was characterized using 1H NMR, Ellman test, TGA and Zetasizer. Cell toxicity studies were performed on Human Embryonic Kidney 293 (Hek293) cell line using XTT method, to investigate the potential effect of this new derivative on cell viability. 1H NMR results showed that all substitution reactions were successfully carried out. Zeta potential of new derivative at acidic and physiological pHs was greater than chitosan and it revealed an increase in solubility of the derivative. Furthermore, it had no significant cytotoxicity against Hek293 cell line in comparison to chitosan. These findings confirm that this new derivative can be introduced as a suitable compound for biomedical purposes.
ISSN:0141-8130
1879-0003
DOI:10.1016/j.ijbiomac.2016.10.094