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

Acta Biomater. 2011 Apr;7(4):1504-15. doi: 10.1016/j.actbio.2010.12.026. Epub 2010 Dec 25.


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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / pharmacology
  • Amino Acids / chemistry
  • Animals
  • Biodegradation, Environmental / drug effects
  • Calorimetry, Differential Scanning
  • Cattle
  • Cell Adhesion / drug effects
  • Cell Proliferation / drug effects
  • Endothelial Cells / cytology*
  • Endothelial Cells / drug effects
  • Fibroblasts / cytology*
  • Fibroblasts / drug effects
  • Humans
  • Hydroxyl Radical / chemistry*
  • Magnetic Resonance Spectroscopy
  • Materials Testing / methods*
  • Polyesters / chemical synthesis*
  • Polyesters / chemistry
  • Polyesters / pharmacology*
  • Solubility / drug effects
  • Spectroscopy, Fourier Transform Infrared
  • Temperature


  • Amides
  • Amino Acids
  • Polyesters
  • Hydroxyl Radical