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, H-1 NMR and C-13 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. (C) 2003 Elsevier Ltd. All rights reserved.