Lu Kai, Shen Xinyi, Shi Yunhai, He Zejian, Zhang Dahong, Zhou Mi
College of Materials Science and Engineering, Zhejiang University of Technology Hangzhou Zhejiang 310014 China.
Stoddart Institute of Molecular Science, Department of Chemistry, Zhejiang University Hangzhou Zhejiang 310027 China
RSC Adv. 2024 May 29;14(25):17440-17447. doi: 10.1039/d4ra02002b. eCollection 2024 May 28.
The Biginelli reaction, a three-component cyclocondensation reaction, is an important member of the multicomponent reaction (MCR) family. In this study, we conducted end-group modifications on a variety of biodegradable polyesters, including poly(1,4-butylene adipate) (PBA), poly(ε-caprolactone) (PCL), polylactic acid (PLA), and poly(-dioxanone) (PPDO), based on the precursor polyethylene glycol (PEG). By combining two polymers through the Biginelli multi-component reaction, four new biodegradable polyester copolymers, namely DHPM-PBA, DHPM-PCL, DHPM-PLA, and DHPM-PPDO, were formed. These Biginelli reactions demonstrated exceptional completeness, validating the efficiency of the synthesis strategy. Although the introduction of various polyesters lead to different properties, such as crystallinity and cytotoxicity, the newly synthesized 3,4-dihydro-2()-pyrimidinone compounds (DHPMs) exhibit enhanced hydrophilicity and can self-assemble in water and ,-dimethylformamide (DMF) solution to form micelles with a controllable size. Furthermore, DHPM-PPDO promotes cellular growth and has potential applications in wound healing and tissue engineering. In conclusion, this method demonstrates great universality and methodological significance and offers insights into the medical applications of polyethylene glycol.
Biginelli反应是一种三组分环缩合反应,是多组分反应(MCR)家族的重要成员。在本研究中,我们基于前体聚乙二醇(PEG)对多种可生物降解聚酯进行了端基修饰,包括聚(1,4-丁二醇己二酸酯)(PBA)、聚(ε-己内酯)(PCL)、聚乳酸(PLA)和聚(-二氧六环酮)(PPDO)。通过Biginelli多组分反应将两种聚合物结合,形成了四种新型可生物降解聚酯共聚物,即DHPM-PBA、DHPM-PCL、DHPM-PLA和DHPM-PPDO。这些Biginelli反应显示出极高的完整性,验证了合成策略的有效性。尽管引入各种聚酯会导致不同的性质,如结晶度和细胞毒性,但新合成的3,4-二氢-2()-嘧啶酮化合物(DHPMs)表现出增强的亲水性,并且可以在水和N,N-二甲基甲酰胺(DMF)溶液中自组装形成尺寸可控的胶束。此外,DHPM-PPDO促进细胞生长,在伤口愈合和组织工程方面具有潜在应用。总之,该方法具有很强的通用性和方法学意义,并为聚乙二醇的医学应用提供了见解。