Synthesis of O,O′-dipalmitoyl chitosan and its amphiphilic properties and capability of cholesterol absorption

The regioselective synthesis of an amphiphilic chitosan derivative, O,O′-dipalmitoyl chitosan (DPCT) was achieved by the selective protection of amino groups in MeSO3H. The amphiphilic behavior and miscibility with cholesterol of DPCT were studied through Langmuir–Blodgett (LB) technique. The condensed monolayer formed at water–air interface had a collapse pressure of 40 mN m−1 and could be transferred onto various substrates by Langmuir–Blodgett technique. Furthermore, this amphiphilic chitosan with free amino groups was cross-linked with glutaraldehyde. The adsorption behavior of the cross-linked amphiphilic chitosan to cholesterol was also studied. The results showed that this cross-linked amphiphilic chitosan could effectively adsorb cholesterol both in polar and in non-polar solvents.