title: Thiolated methylated dimethylaminobenzyl chitosan: A novel chitosan derivative as a potential delivery vehicle.
abstract: 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 using1H 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.
authors.affiliation: Faculty of Pharmacy, International Campus, Tehran University of Medical Sciences, Tehran, Iran.
authors.forename: Shirin
authors.initials: S
authors.lastname: Hakimi
authors.affiliation: Medicinal plants Research Center, Institute of Medicinal Plants, ACECR, Karaj, Iran.
authors.forename: Elaheh
authors.initials: E
authors.lastname: Mortazavian
authors.affiliation: Nanobiotechnology Research Center, Avicenna Research Institute, ACECR, Tehran, Iran. Electronic address: z.mohammadi@avicenna.ac.ir.
authors.forename: Zohreh
authors.initials: Z
authors.lastname: Mohammadi
authors.affiliation: Nanobiotechnology Research Center, Avicenna Research Institute, ACECR, Tehran, Iran.
authors.forename: Fatemeh Yazdi
authors.initials: FY
authors.lastname: Samadi
authors.affiliation: Department of Nanobiotechnology, Faculty of Biological Sciences, Tarbiat Modares University, Tehran, Iran.
authors.forename: Hamidreza
authors.initials: H
authors.lastname: Samadikhah
authors.affiliation: Department of Plant Breeding and Biotechnology, Faculty of Plant Production, Gorgan University of Agricultural Sciences and Natural Resources, Gorgan, Iran.
authors.forename: Sadegh
authors.initials: S
authors.lastname: Taheritarigh
authors.affiliation: Faculty of Medicine, Tehran University of Medical Sciences, Tehran, Iran.
authors.forename: Niyousha Rafiee
authors.initials: NR
authors.lastname: Tehrani
authors.affiliation: Department of Pharmaceutics, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran.
authors.forename: Morteza
authors.initials: M
authors.lastname: Rafiee-Tehrani
mesh_terms: D002470:Cell Survival / Q000187:drug effects; D048271:Chitosan / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000633:toxicity; D004337:Drug Carriers / Q000737:chemistry* / Q000633:toxicity; D057809:HEK293 Cells; D006801:Humans; D012995:Solubility; D013438:Sulfhydryl Compounds / Q000737:chemistry* / Q000633:toxicity
chemical_list: D004337:Drug Carriers; D013438:Sulfhydryl Compounds; C539634:methylated N-(4-N,N-dimethylaminobenzyl)chitosan; D048271:Chitosan
keywords: Cytotoxicity; New chitosan derivative; Synthesis