Preparation, Characterization And Some Biological Activities Of Water Soluble Chitosan Derivatives

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Date
2015-10
Authors
Khalil Suliman, Esra Suliman
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Publisher
Universiti Sains Malaysia
Abstract
The aim of this research is to synthesise novel water-soluble chitosan derivatives and to investigate their physical, chemical as well as antibacterial and anticancer properties. Thus, fourteen chitosan derivatives were synthesised with a wide range of molecular weights (from 0.56 to 286 kDa). Various functional groups, i.e. phenylaniline, benzene-1,3-diol, methylphenol, 8-hydroxyquinoline, 2- aminopyridine, (bis(2-chloroethyl)ether, 4,7,10-trioxa-1,13-tridecanediamine, dicyandiamide, acrylamide, poly(1-vinylpyrrolidone-co-2-dimethylaminoethyl methacrylate) were used to produce the modified chitosans. These derivatives were characterized using various techniques such as Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic resonance spectroscopy (NMR) (proton and carbon-13) elemental analysis, thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). Most of these derivatives showed remarkable solubility in neutral and acidic conditions. The chitosan derivatives showed lower degree of deacetylation than chitosan, and the crystalline state for chitosan was changed to amorphous after the introduction of the functional groups. Most of the derivatives also showed interesting luminescent properties. All derivatives have different antiproliferative effect against three cancer lines when tested in vitro namely prostate, colon and breast cancer at neutral pH. The 4,7,10-trioxa-1,13- tridecanediamine chitosan derivative exhibited mild cytotoxicity against breast cancer cell with IC50 = 109.8 μg mL-1. Bis(2-chloroethyl) ether chitosan showed significant activity against breast cancer MCF-7 with IC50 = 57.25 μg mL-1. 8- Hydroxyquinoline chitosan exhibits the highest antiproliferative effect against the tested cancer cell lines i.e., prostate cancer cell line PC3 with IC50 = 12.11 μg mL-1, breast cancer cell line MCF-7 with IC50 = 14.18 μg mL-1 and colon cancer cell line HCT-116 with IC50 = 79.21 μg mL-1. Antibacterial properties against gram-negative bacteria namely E. coli and gram-positive bacteria namely S. aureus showed Minimum Inhibitory Concentration (MIC) at 1000 μg mL-1 for chitosan. However, most of the chitosan derivatives showed lower MIC values namely from 500 to 62.5 μg mL-1.
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Keywords
Chitosan derivatives
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