title: 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.
authors.affiliation: Department of Fiber Science and Apparel Design, Cornell University, Ithaca, NY 14853, USA.
authors.forename: Mingxiao
authors.initials: M
authors.lastname: Deng
authors.forename: Jun
authors.initials: J
authors.lastname: Wu
authors.forename: Cynthia A
authors.initials: CA
authors.lastname: Reinhart-King
authors.forename: Chih-Chang
authors.initials: CC
authors.lastname: Chu
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000494:pharmacology; D000596:Amino Acids / Q000737:chemistry; D000818:Animals; D001673:Biodegradation, Environmental / Q000187:drug effects; D002152:Calorimetry, Differential Scanning; D002417:Cattle; D002448:Cell Adhesion / Q000187:drug effects; D049109:Cell Proliferation / Q000187:drug effects; D042783:Endothelial Cells / Q000166:cytology* / Q000187:drug effects; D005347:Fibroblasts / Q000166:cytology* / Q000187:drug effects; D006801:Humans; D017665:Hydroxyl Radical / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008422:Materials Testing / Q000379:methods*; D011091:Polyesters / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D012995:Solubility / Q000187:drug effects; D017550:Spectroscopy, Fourier Transform Infrared; D013696:Temperature
chemical_list: D000577:Amides; D000596:Amino Acids; D011091:Polyesters; D017665:Hydroxyl Radical