Ibuprofen-loaded chitosan and chemically modified chitosans—Release features from tablet and film forms

Abstract

The biopolymer chitosan was chemically modified in two sequences of reactions: (i) immobilization of methyl acrylate followed by cysteamine and (ii) the sequence of immobilization reactions involving ethylene sulfide, methyl acrylate and finally cysteamine. In both cases the pendant chains have attached nitrogen, oxygen and sulfur basic centers. The corresponding structures were characterized through elemental analysis, infrared spectroscopy, nuclear magnetic resonance in the solid state for carbon, thermogravimetry and scanning electron microscopy. The newly synthesized biopolymers have abilities to immobilize and controllably release the non-steroidal drug ibuprofen. The ibuprofen-loaded biomaterials as tablets or as films crosslinked with glutaraldehyde revealed that drug release is pH sensitive. The chemically modified chitosan may allow reduction of drug release in stomach fluids, since the functional groups cause a decrease in swelling rate at pH 1.2, opposite to the behavior that occurs at pH 7.4, that of nutritional fluid, where an increase of the rate of swelling occurs. In such conditions the negatively charge ibuprofen is electrostatically repelled by negative chitosan derivative surfaces.