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化学学报
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化学学报 ›› 2008, Vol. 66 ›› Issue (9): 1067-1073. 上一篇    下一篇

研究论文

新型长侧链双羧基功能单体N-(p-乙烯基苄基)-N,N-二[2-(3-羧基丙酰氧基)乙基]胺的合成及其对牛血清白蛋白印迹识别的应用

高吉刚，陈长宝，王荣荣，周杰*   

  1. (山东农业大学化学与材料科学学院 泰安 271018)
  • 投稿日期:2007-08-19 修回日期:2008-01-03 发布日期:2008-05-14
  • 通讯作者: 周杰

Synthesis of a Long Side Chain-Linked and Dually Carboxy Functional Monomer N-(p-Vinylbenzyl)-N,N-bis[2-(3-carboxypropionyloxy)ethyl] amine and Its Application to Recognition of Imprinted Bovine Serum Albumin

GAO Ji-Gang CHEN Chang-Bao WANG Rong-Rong ZHOU Jie*   

  1. (College of Chemistry and Material Science, Shandong Agricultural University, Tai'an 271018)
  • Received:2007-08-19 Revised:2008-01-03 Published:2008-05-14
  • Contact: ZHOU Jie

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设计合成了一种新型功能单体N-(p-乙烯基苄基)-N,N-二[2-(3-羧基丙酰氧基)乙基]胺. 采用质子核磁共振、红外光谱及元素分析对单体分子的结构进行了表征, 利用荧光猝灭法和同步荧光法研究了单体与牛血清白蛋白的结合机理, 结果表明在pH 7.4离子强度为0.5 mol•L－1条件下, 单体与牛血清白蛋白中的色氨酸残基形成稳定的复合物, 其结合比为2∶1, 表观结合常数KA＝2.239×1011 L2•mol－2. 以该单体为功能单体, 牛血清白蛋白为模板分子, N,N'-亚甲基双丙烯酰胺为交联剂和多孔聚偏二氟乙烯膜为支持膜, 在水介质中制备了一个分子印迹聚合物复合膜. 渗透实验表明, 这个印迹复合膜对模板分子牛血清白蛋白的渗透量要远高于对照的人血清白蛋白和卵蛋白, 通过与非分子印迹膜对照也说明了此分子印迹复合膜对模板分子高的渗透选择性.

关键词: N-(p-乙烯基苄基)-N,N-二[2-(3-羧基丙酰氧基)乙基]胺, 模板分子, 牛血清白蛋白, 分子印迹复合膜

N-(p-Vinylbenzyl)-N,N-bis[2-(3-carboxypropionyloxy)ethyl] amine has been designed and synthesized as a novel functional monomer for molecular imprinting, the structure of which was established with elemental analysis, FT-IR and 1H NMR spectroscopy. The binding mechanism between this functional monomer and bovine serum albumin was studied by a fluorescence quenching method and measurement of synchronous fluorescence intensity. These research results indicated that at ionic strength 0.5 mol•L－1 and pH 7.4, the monomer had strong interaction with tryptophan residues of bovine serum albumin. The composition ratio of the complex formed between the monomer and bovine serum albumin is 2∶1, and the apparent binding constant between them is KA＝2.239×1011 L2•mol－2. Based on this study, a molecularly imprinted composite polymeric membrane was prepared over a poly(vinylidene fluoride) film support in aqueous solution using the novel monomer as a functional one, bovine serum albumin as template molecules and N,N'-methylenebisacrylamide as a crosslinker. Permselectivity of the imprinted composite membrane to bovine serum albumin was tested by diffusion experiments. These results showed that the imprinted composite membrane exhibited higher transport selectivity to the template molecule bovine serum albumin than human serum albumin and ovum protein. The diffusion experiments for the imprinted and non-imprinted membranes indicated that the imprinted one also took on high permselectivity for the template molecule bovine serum albumin in comparison with the non-imprinted one.

Key words: N-(p-vinylbenzyl)-N,N-bis[2-(3-carboxypropionyloxy)ethyl] amine, template molecule, bovine serum albumin, molecularly imprinted composite membrane