Preparation, Characterization And Some Biological Activities Of Water Soluble Chitosan Derivatives
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Date
2015-10
Authors
Khalil Suliman, Esra Suliman
Journal Title
Journal ISSN
Volume Title
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.
Description
Keywords
Chitosan derivatives