One-Pot Photo-Induced Sequential CuAAC and Thiol-Ene Click Strategy for Bioactive Macromolecular Synthesis
One-Pot Photo-Induced Sequential CuAAC and Thiol-Ene Click Strategy for Bioactive Macromolecular Synthesis
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DOI：
10.1021/ma5007039
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发表时间：
2014-06-10
期刊：
影响因子：
5.5
通讯作者：
Yagci, Yusuf
中科院分区：
文献类型：
--
作者：
Doran, Sean;Murtezi, Eljesa;Yagci, Yusuf
概念上新的一锅光诱导顺序点击反应实现了新的嵌段共聚物具有细胞粘附能力。以丙炔醇为原料，在八酸锡存在下，在110℃下开环聚合，再与甲基丙烯酸酯化，制备了链端具有可点击官能团的聚（ε -己内酯），即α -炔基- ω -烯基-聚（ε -己内酯）（A-PCL-MA）。采用原子转移自由基聚合（ATRP）和叠氮化钠叠氮化反应制备了叠氮化官能团聚甲基丙烯酸甲酯（PMMA-N-3）。最后，a - pcl - ma与PMMA-N-3和n -乙酰- l-半胱氨酸（NAC）通过光诱导连续点击反应在一锅工艺中反应，得到所需的生物活性嵌段共聚物（PMMA-b-PCL-NAC）。用所得的嵌段共聚物PMMA-b-PCL-NAC制备细胞粘附基质，测定细胞在基质上的增殖情况。来自Vero细胞系（非洲绿猴肾上皮）的细胞在基质上孵育，48小时后，它们比市售的细胞培养板显示出更大的细胞增殖。
Conceptually new one-pot photoinduced sequential click reactions were implemented to yield novel block copolymers with the ability for cell adhesion. Poly(epsilon-caprolcatone) possessing clickable functional groups at the chain ends, namely alpha-alkynyl-omega-alkenyl-poly(epsilon-caprolactone) (A-PCL-MA), was prepared by ring-opening polymerization of epsilon-caprolactone using propargyl alcohol in the presence of stannous octoate at 110 degrees C followed by esterification with methacrylic acid. Azide-functional poly(methyl methacrylate) (PMMA-N-3) was prepared independently by atom transfer radical polymerization (ATRP) followed by an azidation process using sodium azide. Finally, A-PCL-MA was reacted with PMMA-N-3 and N-acetyl-L-cysteine (NAC) in a one-pot process through photoinduced sequential click reactions to furnish desired bioactive block copolymer (PMMA-b-PCL-NAC). A matrix for cell adhesion was then prepared from the yielded block copolymer PMMA-b-PCL-NAC and cell proliferation on the matrix was measured. Cells from the Vero cell line (African green monkey kidney epithelial) were incubated on the matrix, and after 48 h, they showed greater cell proliferation than the commercially available cell culture plates used as comparison.