Biodegradable functional poly(ester amide)s with pendant hydroxyl functional groups: Synthesis, characterization, fabrication and in vitro cellular response

Abstract

The synthesis of a new family of biodegradable α-amino acid poly(ester amide)s (AA-PEAs) with pendant benzyl ether groups and hydroxyl functional groups is reported. The synthetic strategy employs the ring opening reaction of O-benzyl-l-serine-N-carboxyanhydride with di-p-toluenesulfonic acid salts of bis-l-valine butane-1,4-diester, followed by solution polycondesation reactions with di-p-nitrophenyl sebacate in N,N-dimethylacetamide. Catalytic hydrogenation of the resulting benzyl ether protected AA-PEAs (PEA-Ser-Bzs) was performed to restore the hydroxyl functional groups in the functionalized AA-PEAs (PEA-Ser-OH). All resulting polymers were characterized by standard physico-chemical methods. The pendant hydroxyl groups in PEA-Ser-OH were used to fabricate AA-PEA-based gels via acrylation and photo-gelation. The cell–polymer interactions of PEA-Ser-Bz and PEA-Ser-OH were evaluated in terms of cell attachment and proliferation assay using bovine aortic endothelial cells (BAECs) as well as fibroblasts. The cell culture data indicated that the hydrophobic/hydrophilic characteristics (from contact angle data) of these AA-PEAs could significantly affect the interaction between BAECs and AA-PEA. This finding may provide additional possible applications for this new family of functionalized AA-PEA polymers.