Preparation of N-alkyl-O-sulfate chitosan derivatives and micellar solubilization of taxol

A series of novel chitosan derivative carrying long chain alkyl groups (n=8,10,12) as hydrophobic moieties and sulfated groups as hydrophilic moieties were synthesized. The chemical structure of chitosan derivatives were characterized by elemental analysis, FTIR, 1H NMR and 13C NMR. Some physical properties of chitosan derivative were measured by TG and WAXD. Polymeric micelles of size around 100–400 nm were formed in water from the derivative. Taxol, a water insoluble anticancer drug, was solubilized into the polymeric micelle by physical entrapment. The result shows that the taxol concentration in the N-octyl-O-sulfate chitosan (OCS1) micellar solution was 2.01 mg/ml, which was much higher than that in water (<0.001 mg/ml). So N-octyl-O-sulfate chitosan (OCS1) micelle may be useful as a carrier for taxol.