基于迈克尔加成的生物硫醇比率比色荧光探针  

A Ratiometric and Colormetric Fluorescent Probe for Biothiols Based on Michael Addition

作　　者：王晓菊[1] 王云侠 张彩红[2] WANG Xiaoju;WANG Yunxia;ZHANG Caihong(Institute of Molecular Science,Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education,Shanxi University,Taiyuan 030006,China;School of Chemistry and Chemical Engineering,Shanxi University,Taiyuan 030006,China)

机构地区：[1]山西大学分子科学研究所,教育部化学生物学与分子工程实验室,山西太原030006 [2]山西大学化学化工学院,山西太原030006

出　　处：《山西大学学报（自然科学版）》2020年第2期328-333,共6页Journal of Shanxi University(Natural Science Edition)

基　　金：国家自然科学基金(21601111,21807067)。

摘　　要：小分子生物硫醇(RSH),包括半胱氨酸(Cys)、同型半胱氨酸(Hcy)和谷胱甘肽(GSH)作为重要的细胞成分,在生理和病理过程中发挥着多种作用。文章设计合成了一种新型的比色荧光探针,N-丁基-4-(2,4-己二烯酸)酯-1,8-萘二酰亚胺(BHENA),用于检测生物硫醇。用紫外可见分光光度法和荧光光谱法研究了探针对RSH的识别行为。结果表明,探针BHENA对RSH的响应明显强于其他不含硫醇的氨基酸和常见阴离子。特别之处在于,BHENA对RSH的响应同时表现出溶液颜色(从无色到黄色)和荧光光谱(从蓝色到黄绿色)两种特征的变化。探针BHENA与RSH的作用机制为迈克尔加成反应和分子内环化过程。Low molecular weight biothiols(RSH),including cysteine(Cys),homocysteine(Hcy),and glutathiones(GSH)are very important cellular components that play numerous roles in physiological and pathological processes.A novel colormetric fluorescent probe,N-butyl-4-(2,4-hexadienoic acid)ester-1,8-naphthalimide(BHENA),for biothiols with ratiometric feature was designed and synthesized.The recognition behaviors for RSH were investigated by UV-vis and fluorescence spectra.The results showed that BHENA processed an obviously stronger response to RSH than other non-thiol-bearing amino acids and common anions.Interestingly,the response of BHENA for RSH displayed simultaneously two features including solution color(from colorless to yellow)and fluorescence spectra(from blue to yellow-green)changes.The action mechanism included Michael addition followed by an intramolecular cyclization processes.

关 键 词：1 8-萘二酰亚胺 生物硫醇 比率荧光探针 

分 类 号：O657.3[理学—分析化学]