基于苯并吡喃腈的激活型半胱氨酸荧光探针  

A Turn-On Fluorescent Probe for Cysteine Based on Benzopyran

作　　者：杨婷婷[1] 郭志前[1] 邵安东[1] 赵平[1] 朱为宏[1] 

机构地区：[1]华东理工大学精细化工研究所,上海200237

出　　处：《应用化学》2016年第4期397-405,共9页Chinese Journal of Applied Chemistry

基　　金：国家自然科学基金项目(61306022)资助~~

摘　　要：设计并合成了基于苯并吡喃腈为母体单元的近红外激活型荧光探针（E）-2-（苯并吡喃腈基）乙烯基-5-（二乙氨基）丙烯酸苯酯（DCM-AC）,其结构中的丙烯酰酯键作为氨基酸激活反应的响应基团。研究结果表明,探针分子DCM-AC对半胱氨酸具有高灵敏、选择性光谱响应,不仅能观察到明显的颜色变化,而且探针在710 nm处的荧光发射强度显著增强,相应的荧光增强比值与半胱氨酸的浓度（1.0-8.0μmol/L）呈现良好的线性关系。探针DCM-AC对半胱氨酸的检出限为2.8×10^-7mol/L,能选择性检测半胱氨酸区别于结构类似的高半胱氨酸和谷胱甘肽,且不受其它氨基酸物质干扰。通过质谱、核磁和紫外吸收光谱研究了DCM-AC检测半胱氨酸的反应激活机理：半胱氨酸先通过巯基与DCM-AC上的丙烯酰酯双键发生亲核加成,然后环化脱除内酰胺环状化合物。A benzopyran-based turn-on near-infrared probe（ E）-2-（ benzopyran） ethenyl-5-（ diethylamino）phenyl acrylate（ DCM-AC） has been successfully synthesized. Acrylate bond is specifically designed for the response units of amino acid. The results show that the spectral response of DCM-AC towards cysteine is highly sensitivity and selectivity. With increasing the concentration（ 1. 0 - 8. 0 μmol / L） of cysteine,a significant color change can be observed and the fluorescent intensity of DCM-AC at 710 nm increases gradually,showing a good linear relationship with concentration. The limit of detection of DCM-AC for cysteine is determined as2. 8 × 10^- 7mol / L. DCM-AC exhibits a highly selective probe for cysteine over homocysteine and glutathione,with no interference of other substances. The recognition mechanism of the DCM-AC to cysteine is verified by mass spectrum,1H NMR titration and absorption spectra,indicating that cysteine thiol groups attack at acrylate double bond of DCM-AC by addition reaction,and finally removed as the cyclic lactam compound.

关 键 词：半胱氨酸 荧光探针 苯并吡喃腈 选择性 

分 类 号：O656.2[理学—分析化学]