Preparation and evaluation of photocrosslinkable chitosan as a drug delivery matrix

Epichlorohydrin (1‐chloro‐2,3‐epoxypropane) was reacted with sodium azide in the presence of a phase transfer catalyst to obtain 1‐chloro‐2‐hydroxy‐3‐azidopropane, which was further coupled onto chitosan to prepare a photocrosslinkable derivative of the biopolymer. Elemental analysis and infrared (IR) spectroscopy confirmed the incorporation of azide groups onto chitosan. Films were cast from an aqueous acetic acid solution of azidated chitosan containing a model drug, such as theophylline. Irradiation of the film with ultraviolet (UV) light led to crosslinking of the drug incorporated film. IR spectra indicated complete surface crosslinking within 2 h of irradiation. Release of theophylline from uncrosslinked and crosslinked films was examined in simulated gastric and intestinal fluids without enzymes at 37 °C. The release of the drug from the crosslinked films was slower than the release from uncrosslinked films. Although the system is far from being optimized to obtain sustained release of a pharmacologically active agent for long periods, the data obtained indicate the possibility of developing photocrosslinkable matrices of biopolymers, such as chitosan, for sustained drug delivery with many advantages over chemical crosslinking. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 86: 1873–1877, 2002