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Synthesis of biodegradable polyurethanes chain-extended with (2S)-bis(2-hydroxypropyl) 2-aminopentane dioate

机译:可生物降解的聚氨酯的合成与(2S) - (2-羟丙基)2-氨基戊烷二酯延伸

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Polyurethanes (PUs) are the most widely used polymers because of their biocompatibility, tunable mechanical properties, and chemical versatility. In this study, a two-step condensation polymerization of polycaprolactone diol and hexamethylene diisocyanate was carried out, and a glutamic acid ester derivative, (2S)-bis(2-hydroxypropyl) 2-aminopentane dioate (HPAP), was used as a new chain extender to accelerate the biodegradation properties of PU. HPAP was synthesized by the Fischer esterification of L-glutamic acid. The chemical structure of HPAP was confirmed by high-resolution mass spectroscopy and m/z (EI) was found to be 264.1447 [calculated value = 264.1443 for C11H21NO6 (M+)]. The Berry plot of static light-scattering measurements showed that PU-HPAP had a weight-average molecular weight and radius of gyration of 33,100 g/mol and 1420 nm, respectively. The presence of HPAP in the PU structure facilitated hydrogen bonding between the polymer chains and increased the glass-transition temperature from -56 degrees C (PU) to -50 degrees C (PU-HPAP). PU-HPAP showed the highest hydrophilicity and surface free energy among all of samples, and this accelerated the in vitro biodegradation period via surface erosion. In addition, PU-HPAP did not show any cytotoxic effects on the L929 cells. A new biodegradable and biocompatible PU-HPAP was obtained as candidate for tissue engineering applications. (C) 2017 Wiley Periodicals, Inc.
机译:聚氨酯(PUS)是最广泛使用的聚合物,因为它们的生物相容性,可调谐机械性能和化学多功能性。在本研究中,进行了两步缩聚聚合的聚己内酯二醇和六亚甲基二异氰酸酯,并且谷氨酸酯衍生物(2S)-BIS(2-羟丙基)2-氨基戊烷(HPAP)用作新的链扩展器加速PU的生物降解特性。通过L-谷氨酸的Fischer酯化合成HPAP。通过高分辨率质谱证实了HPAP的化学结构,并发现了M / Z(EI)为264.1447 [C11H21NO6(M +)的值= 264.1443]。静态光散射测量的浆果曲线图显示PU-HPAP分别具有33,100g / mol和1420nm的重均分子量和旋转半径。 PU结构中HPAP的存在促进了聚合物链之间的氢键,并从-56℃(PU)至-50℃(PU-HPAP)增加了玻璃化转变温度。 PU-HPAP在所有样品中显示出最高的亲水性和表面自由能,并通过表面腐蚀加速了体外生物降解期。此外,PU-HPAP未对L929细胞显示任何细胞毒性作用。获得了一种新的可生物降解和生物相容性PU-HPAP作为组织工程应用的候选者。 (c)2017 Wiley期刊,Inc。

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