Synthesis of poly (glycerol-co-dioate-co-butanedioate-co-xanthorrhizol) ester and a study of chain length effect on pendant group loading

Abstract

Natural R-(-)-xanthorrhizol possess a number of therapeutic activities including anti-cancer. The pharmacokinetic properties of that poorly aqueous soluble compound could be improved by incorporating it into polymeric materials. Glycerol can produce a functionalized polymer through a polycondensation process. Enzymatic polycondensation of glycerol and divinylesters was studied and xanthorrhizol was covalently loaded via a butanedioate linker to the polymer backbone. It was observed that xanthorrhizol loading to the polymer backbone increases with the increasing of the chain length of a dioate moiety. Enzyme-mediated xanthorrhizol release from a polymer backbone shows that the polymeric prodrug is able to release xanthorrhizol in a sustained manner. Therefore, the approach described here might be valuable for controlled loading and release of such phenolic sesquiterpenes from the polymeric prodrug. (C) 2012 Elsevier B.V. All rights reserved.