Synthesis and Evaluation of Cytocompatible Alkyne-Containing Poly(β-amino ester)-Based Hydrogels Functionalized via Click Reaction,ACS Macro Letters

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Synthesis and Evaluation of Cytocompatible Alkyne-Containing Poly(β-amino ester)-Based Hydrogels Functionalized via Click Reaction
ACS Macro Letters ( IF 5.1 ) Pub Date : 2020-09-01 , DOI: 10.1021/acsmacrolett.0c00545
Ke Yao ₁ , Guangming Gong ₂ , Zexi Fu ₁ , Yuqing Wang ₁ , Luzhong Zhang ₁ , Guicai Li ₁ , Yumin Yang ₁

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Although poly(β-amino esters) (PAEs) have been widely applied in nonviral gene transfection, drug delivery systems, and regenerative medicine, the multifunctional modification of PAEs and bio-orthogonal strategies of PAE-based hydrogel functionalization is still a challenge. Herein, a strategy of poly(β-amino ester)-based hydrogel functionalization was developed via bio-orthogonal reactions in this study. Acrylate-terminated poly(β-amino esters) containing alkyne groups were synthesized by Michael addition reaction. Alkyne groups on poly(β-amino esters) could conjugate bioactive molecules with azide of K(N₃)RGD via copper-catalyzed azide–alkyne cycloaddition, and terminal acrylate groups could in situ polymerize to prepare a hydrogel. A biomimetic peptide K(N₃)RGD functionalized hydrogel was prepared by polymerization of acrylate-terminated poly(β-amino esters) containing conjugated peptide and polyethylene glycol diacrylate (PEGDA). The storage modulus and mechanical properties exhibited an increased trend with the increased concentration; nevertheless, swelling ratio and surface wetting properties demonstrated a decreased tendency by increased concentrations. Cell proliferation and live/dead staining showed that Schwann cells plated on the hydrogel with an elastic modulus of 25.39 KPa are more suitable for proliferation and function exertion of Schwann cells compared with that of 42.11 and 57.86 KPa, and KRGD-conjugated hydrogel could increase the elongation of Schwann cells relative to nonconjugated hydrogels. This azide–alkyne strategy may be a promising candidate for hydrogel functionalization in tissue engineering and other biomedical applications.

中文翻译：

通过点击反应功能化的含细胞相容性炔烃聚 (β-氨基酯) 水凝胶的合成和评价

尽管聚（β-氨基酯）（PAEs）已广泛应用于非病毒基因转染、药物递送系统和再生医学，但 PAEs 的多功能修饰和基于 PAE 的水凝胶功能化的生物正交策略仍然是一个挑战。在此，本研究通过生物正交反应开发了一种基于聚（β-氨基酯）的水凝胶功能化策略。通过迈克尔加成反应合成含有炔基的丙烯酸酯封端的聚（β-氨基酯）。聚(β-氨基酯)上的炔基可以通过铜催化的叠氮化物-炔烃环加成将生物活性分子与K(N _{3 )RGD的叠氮化物结合，末端丙烯酸酯基团可以}原位聚合制备水凝胶。一种仿生肽K(N ₃)RGD 功能化水凝胶是通过聚合含有共轭肽和聚乙二醇二丙烯酸酯 (PEGDA) 的丙烯酸酯封端的聚 (β-氨基酯) 制备的。储能模量和力学性能随浓度的增加呈增加趋势；然而，溶胀比和表面润湿性能表现出随浓度增加而降低的趋势。细胞增殖和活/死染色表明，与42.11和57.86 KPa相比，弹性模量为25.39 KPa的水凝胶上的施万细胞更适合施万细胞的增殖和功能发挥，KRGD共轭水凝胶可以增加雪旺细胞相对于非共轭水凝胶的伸长率。

更新日期：2020-09-15

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