Synthesis and study of hyaluronic acid derivatives modified on carboxyl

Charles University Faculty of Pharmacy in Hradec Králové Department of Organic and Bioorganic Chemistry Author: Gabriela Volfová Supervisors: Mgr. Radovan Bu a, Ph.D. doc. PharmDr. Jaroslav Roh, Ph.D. Title: Synthesis and study of hyaluronic acid derivatives modified on carboxyl Abstract: Hyaluronic acid (HA) is a naturally occurring linear polysaccharide. Due to its biocompatibility and non-immunogenicity, HA and its derivatives are widely used in various biological and medical applications. The e cacy of each formulation is strongly related to the molecular weight (MW) of the HA used. Unfortunately, various factors can a ect the MW during the manufacturing process. Elevated tem- perature required during the sterilization process is one significant example, which can lead to a reduction in molecular weight and result in a loss of some desired properties of the final product. This work focuses on the synthesis of HA amides formed on its free carboxyl group and subsequently studying the e ect of this modifi- cation on the degradation rate at elevated temperature. Three final compounds were prepared by reacting HA with various amines using 4-(4,6-dimethoxy-1,3,5-triazin-2- yl)-4-methylmorpholinium chloride (DMTMM), all of which underwent degradation noticeably faster than native HA