Acta Chimica Sinica ›› 2008, Vol. 66 ›› Issue (9): 1067-1073. Previous Articles     Next Articles

Original Articles

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)
  • 收稿日期:2007-08-19 修回日期:2008-01-03 出版日期:2008-05-14 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 Online:2008-05-14 Published:2008-05-14
  • Contact: ZHOU Jie

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