A new family of functional biodegradable arginine-based polyester urea urethanes: Synthesis, chracterization and biodegradation

A new family of biodegradable functional cationic l-Arginine (l-Arg) poly (ester urea urethane) (Arg-PEUU) polymers was synthesized by the solution polycondensation of three monomers: l-Arg hydrochloride alkylene diester (Arg-x-Cl), hexamethylene diisocyanate (HDI) and glycerol α-monoallyl ether (GAE). Chemical structures of Arg-x-Cl and the Arg-PEUU polymers were characterized by H NMR, FTIR, and carbon/nitrogen elemental analysis. The molecular weight of Arg-PEUU ranged from 23,900 to 29,400 kg/mol. The glass transition temperature (Tg) of Arg-PEUU ranged from −20.8 °C to 4.2 °C, depending on the feed ratio of the 3 monomers. The water contact angle of Arg-PEUU ranged from 26.7 ± 4.3° to 61.3 ± 5.2°. The Arg-PEUU had no cytotoxicity toward porcine aortic valve smooth muscle cells at low concentrations (0.1–0.2 mg/mL). Arg-PEUUs can be photo-crosslinked into elastic gels with compressive modulus ranged from 54.2 ± 9.1 to 120.7 ± 5.4 KPa. The biodegradation data (weight loss) of the Arg-PEUU in a lipase media suggested that the crosslinking density as well as the Arg-x-Cl contents in the functional Arg-PEUU had a profound impact on the biodegradation rate.