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Antioxidant Polymers via the Kabachnik‐Fields Reaction to Control Cellular Oxidative Stress
Macromolecular Bioscience ( IF 4.6 ) Pub Date : 2020-09-28 , DOI: 10.1002/mabi.201900419
Xianzhe He 1 , Guoqiang Liu 1 , Ye Tian 1 , Tengfei Mao 1 , Haibo Wu 1 , Yen Wei 1 , Lei Tao 1
Affiliation  

Small molecular antioxidants are almost ineffective in regulating harmful oxidative stress in vivo because of their poor bioavailability. Polymer antioxidants are a promising alternative to address this issue, but their laborious synthetic routes limit their development. In this study, aliphatic and aromatic aldehydes are used to synthesize a family of polymers containing different α‐aminophosphonate pendant groups via a facile one‐pot method that combines the Kabachnik–Fields (KF) reaction and free radical polymerization. The structure–property relationship study of these polymers reveals the KF moieties in polymer structures confer radical scavenging ability on polymers. The radical scavenging ability and cytotoxicity of these polymers are evaluated in a stepwise manner to identify a biocompatible polymer antioxidant that can effectively protect the cells from H2O2‐induced oxidative damage. This is the first attempt to develop antioxidative polymers by the KF reaction. It highlights the feasibility of synthesizing new functional polymers using multicomponent reactions, which has important implications for organic and polymer chemistry.

中文翻译:

通过 Kabachnik-Fields 反应控制细胞氧化应激的抗氧化聚合物

小分子抗氧化剂由于其生物利用度差,在调节体内有害氧化应激方面几乎无效。聚合物抗氧化剂是解决这一问题的有前途的替代品,但其繁琐的合成路线限制了它们的发展。在这项研究中,通过结合 Kabachnik-Fields (KF) 反应和自由基聚合的简便的单锅法,使用脂肪族和芳香族醛合成了一系列含有不同 α-氨基膦酸酯侧基的聚合物。这些聚合物的结构-性能关系研究揭示了聚合物结构中的 KF 部分赋予聚合物自由基清除能力。2 O 2诱导的氧化损伤。这是通过 KF 反应开发抗氧化聚合物的首次尝试。它强调了使用多组分反应合成新功能聚合物的可行性,这对有机和聚合物化学具有重要意义。
更新日期:2020-09-28
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