Synthesis, characterization and biodegradation of functionalized amino acid-based poly(ester amide)s.
A series of biodegradable functional amino acid-based poly(ester amide)s (PEA-AG) were designed and synthesized by the solution co-polycondensation of amino acid (L-phenylalanine and DL-2-allylglycine) based monomers and dicarboxylic acid based monomers. Pendant carbon-carbon double bonds located in the DL-2-allylglycine were incorporated into these PEA-AGs, and the double bond contents could be adjusted by tuning the feed ratio of L-phenylalanine to DL-2-allylglycine monomers. Chemical structures of this new functional PEA-AG family were confirmed by FTIR and NMR spectra. The thermal properties of these polymers were investigated; increasing the methylene chain in both the amino acid and dicarboxlic acid segments resulted in a reduction in the polymer glass-transition temperature. The short-term in vitro biodegradation properties of PEA-AGs were investigated as a function of PEA-AG chemical structures and enzymes. Based on the weight loss data, PEA-AGs biodegraded much faster in an enzyme solution than in a PBS buffer solution. The utility of the pendant functional carbon-carbon double bonds in PEA-AG was demonstrated by synthesizing additional functional PEA derivatives. The incorporation of the functional pendant carbon-carbon double bonds along the PEA-AG chains could significantly expand the biomedical applications of these functional PEA-AGs via either their capability to conjugate bioactive agents or prepare additional useful functional derivatives.
Pang
Xuan
X
Department of Fiber Science and Apparel Design, Cornell University, Ithaca, NY 14853-4401, USA.
Chu
Chih-Chang
CC
D000501:Allylglycine / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D001557:Benzenesulfonates / Q000138:chemical synthesis / Q000737:chemistry; D001672:Biocompatible Materials / Q000138:chemical synthesis* / Q000737:chemistry*; D001673:Biodegradation, Environmental; D002918:Chymotrypsin / Q000378:metabolism; D003998:Dicarboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D008855:Microscopy, Electron, Scanning; D010649:Phenylalanine / Q000737:chemistry; D012995:Solubility; D017550:Spectroscopy, Fourier Transform Infrared; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013499:Surface Properties; D013696:Temperature; D013997:Time Factors
D000577:Amides; D000596:Amino Acids; D001557:Benzenesulfonates; D001672:Biocompatible Materials; D003998:Dicarboxylic Acids; D004952:Esters; D013438:Sulfhydryl Compounds; D000501:Allylglycine; D010649:Phenylalanine; D002918:Chymotrypsin; C029501:4-toluenesulfonic acid