Methylated 4-N,N dimethyl aminobenzyl N,O carboxymethyl chitosan as a new chitosan derivative: Synthesis, characterization, cytotoxicity and antibacterial activity.
Chitosan, as a biocompatible polymer, is very attractive for biomedical applications. Continues studies are performing for improving its physicochemical features in order to make it more suitable for such approaches. In this study, methylated 4-N,N dimethyl aminobenzyl N,O carboxymethyl chitosan (MABCC) was synthesized,as a new chitosan derivative, in three steps. The investigations were carried out using FTIR, NMR, TGA and zeta potential measurement. Antibacterial and cell viability assessments were performed on four bacterial strains and two cell lines respectively. FTIR and NMR results showed that all substitution reactions were successfully carried out. Zeta potential of MABCC at various pH especially alkaline pH was greater than chitosan and it revealed increasing the solubility of the derivative. Antibacterial activity of MABCC was extremely greater than chitosan especially in Gram positive bacteria.Furthermore,it had no significant cytotoxicity against MCF-7 and Skov-3 cell lines in comparison to chitosan. These findings confirm that this new derivative can be introduced as a suitable compound for biomedical purposes.
Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran.
Soheila
S
Rahmani
Nanobiotechnology Research Center, Avicenna Research Institute, ACECR, Tehran, Iran. Electronic address: Z.Mohammadi@avicenna.ac.ir.
Zohreh
Z
Mohammadi
Departments of Medicinal Chemistry, Faculty of Pharmacy and Drug Design and Development Research Center, Tehran University of Medical Sciences, Tehran, Iran.
Mohsen
M
Amini
Department of Microbiology, Afzalipour School of Medicine, Kerman University of Medical Sciences, Kerman, Iran.
Elham
E
Isaei
Department of Plant Breeding and Biotechnology, Faculty of Plant Production, Gorgan University of Agricultural Sciences and Natural Resources, Gorgan, Iran.
Sadegh
S
Taheritarigh
Faculty of Medicine, Tehran University of Medical Sciences, Tehran, Iran.
Niyousha
N
Rafiee Tehrani
Departments of Pharmaceutics and Nanotechnology Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran.
Morteza
M
Rafiee Tehrani
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D060326:Chemistry Techniques, Synthetic; D048271:Chitosan / Q000031:analogs & derivatives / Q000737:chemistry*; D006801:Humans; D061986:MCF-7 Cells; D008745:Methylation
D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D048271:Chitosan
4 N,N dimethylaminobenzaldehyde (PubChem CID: 7479); Antibacterial activity; Chitosan derivative; Cytotoxicity; Isopropanol (PubChem CID: 3776); Methyl iodide (PubChem CID: 6328); Monobromoacetic acid (PubChem CID: 6227); N-methylpyrolidone (PubChem CID: 13387); Ninhydrine (PubChem CID: 10236); Sodium borohydride (PubChem CID: 22959485); Triethylamine (PubChem CID: 8471)