Synthesis of Chitosan Microspheres Containing Pendant Cyclodextrin Moieties and their Interaction with Biological Active Molecules

Abstract

A new route to obtain chitosan derivatives containing cyclodextrin moieties as pendant groups was developed. The chitosan microspheres, obtained through crosslinking with glutaraldehyde of an acetic acid solution of chitosan, in an organic suspension medium, were reacted with chloroacyl cyclodextrins in organic basic solvents. The acyl cyclodextrin moieties are linked to the chitosan microspheres through C-N bonds, with the elimination of HCl; higher amounts of acyl cyclodextrin are linked to the microspheres with a smaller crosslinking degree. The chitosan-cyclodextrin conjugates retain higher amounts of bioactive substances (nalidixic acid, piroxicam) or of p-nitrophenol (model substance) than their parent chitosan supports, both by ionic forces and by the formation of inclusion complexes in the cyclodextrin inner cavities. After these preliminary studies, one can appreciate that the cyclodextrin-chitosan conjugates could be used as supports for chromatographic separations or controlled release drug systems.