Syntheses, characterization, and functionalization of poly(ester amide)s with pendant amine functional groups

Poly(ester amide)s (PEAS) comprising a-amino acids, diols, and diacids are promising materials for biomedical applications such as tissue engineering and drug delivery because of their tunability and potential for either hydrolytic or enzymatic degradation. Although a number of PEAs of different compositions have been reported, there is a significant need for the incorporation of amino acids with functional side chains. This will allow for the conjugation of drugs or cell signaling molecules in tissue engineering scaffolds, thus expanding the potential applications of these materials. The objective of this work was the incorporation Of L-lysine into PEAS to provide functionalizable pendant amine groups. Thus, varying percentages of lysine were incorporated into PEAS comprised of L-phenylalanine, 1,4-butanediol, and succinic acid by tuning the ratio of E-protected-L-lysine and L-phenylalanine derived monomers. The polymers were characterized by nuclear magnetic resonance spectroscopy, infrared spectroscopy, size exclusion chromatography, and differential scanning calorimetry. The lysine epsilon-protecting group was removed, then the reactivity of the pendant amines was demonstrated by reaction with amino acid and tri(ethylene glycol) derivatives. The degradation of thin films of polymers were studied using scanning electron microscopy and the incorporation of lysine was found to significantly accelerate both the hydrolytic and enzymatic degradation. (C) 2008 Wiley Periodicals, Inc.