Department of Fiber Science and Apparel Design, Cornell University, Ithaca, NY 14853-4401, USA.
Biomaterials. 2010 May;31(14):3745-54. doi: 10.1016/j.biomaterials.2010.01.027. Epub 2010 Feb 19.
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.
一系列可生物降解的功能性氨基酸基聚酯酰胺(PEA-AG)通过氨基酸(L-苯丙氨酸和 DL-2-烯丙基甘氨酸)基单体和二羧酸基单体的溶液共缩聚合成。DL-2-烯丙基甘氨酸中的侧挂碳-碳双键被引入到这些 PEA-AG 中,并且通过调节 L-苯丙氨酸与 DL-2-烯丙基甘氨酸单体的进料比,可以调整双键的含量。通过 FTIR 和 NMR 光谱证实了这种新型功能性 PEA-AG 家族的化学结构。研究了这些聚合物的热性能;在氨基酸和二羧酸段中增加亚甲基链会导致聚合物玻璃化转变温度降低。通过 PEA-AG 的化学结构和酶来研究 PEA-AG 的短期体外生物降解性能。根据重量损失数据,PEA-AG 在酶溶液中的降解速度比在 PBS 缓冲溶液中快得多。通过合成额外的功能性 PEA 衍生物,展示了 PEA-AG 中侧挂功能碳-碳双键的用途。通过 PEA-AG 链上的功能性侧挂碳-碳双键的引入,可以通过它们结合生物活性物质的能力或制备其他有用的功能性衍生物,显著扩展这些功能性 PEA-AG 在生物医学中的应用。