Synthesis and characterization of a dithiodiglycolic acid-incorporated poly(glycerol sebacate) exhibiting lipase resistance and antibacterial properties

Abstract

Poly(glycerol sebacate) (PGS), a crosslinked network synthesized by polycondensation of glycerol and sebacic acid, has found successful utilization in various tissue engineering applications because of its biocompatibility, ease of synthesis, surface-erosion biodegradability, rubber-like elasticity, and adjustable mechanical properties. However, its fast in vivo degradation and lack of intrinsic antibacterial activity may be a concern for specific applications. The functional groups of glycerol and sebacic acid can react with those of other monomers, offering unlimited possibilities for generating new crosslinked networks tailored for particular purposes. Herein, we synthesized a series of poly(glycerol sebacate dithiodiglycolate) (PGSDTG) by incorporation of dithiodiglycolic acid (DTG) in the synthesis of PGS. PGSDTG exhibited reduced stiffness, sensitivity to glutathione (GSH), resistance to lipase degradation, and inhibition of bacterial adhesion and growth. The PGSDTG containing 45.6 wt% of DTG exhibited the lowest degradation rate with more than 80 wt% of PGSDTG remained at day 28 and the lowest bacterial inactivation rates of 99.2 ± 0.5 % and 82.5 ± 11.0 % against S. aureus and E. coli, respectively. This study suggested that PGSDTG may serve as a suitable antibacterial scaffold material for repairing or regenerating tissues characterized by a slow healing rate.