摘要
本文设计合成了一种基于硫醇-色烯点击反应的荧光探针CHMPC-Ac,用于半胱氨酸(Cys)、同型半胱氨酸(Hcy)和谷胱甘肽(GSH)的识别检测.这些生物硫醇因巯基的强亲核性而与探针的不饱和酮发生迈克尔加成反应,导致色烯分子开环等分子内级联反应,生成具有强荧光的香豆素衍生物,分别使荧光强度增强107、69和66倍.CHMPC-Ac具有灵敏度高(Cys:15 nM;Hcy:26 nM;GSH:22 nM)和响应快(Cys:20 s;Hcy:50 s;GSH:30 s)等优点,并已应用于HepG 2细胞和斑马鱼体内生物硫醇的识别检测.
A new fluorescent probe CHMPC-Ac for biothiol was designed and synthesized based on thiol-chromene click reaction.Nucleophilic addition of sulfydryl group to the unsaturated ketones in CHMPC-Ac induced chromene ring opening and then triggered the intramolecular cascade reaction to generate coumarins with strong fluorescence.The fluorescence intensity can be enhanced by as much as 107,69 and 66 times,respectively.Meanwhile,CHMPC-Ac showed some advantages,such as high sensitivity(Cys:15 nM;Hcy:26 nM;GSH:22 nM)and fast response(Cys:20 s;Hcy:50 s;GSH:30 s).Moreover,it has been successfully applied to image biothiol in HepG2 cells and zebrafish.
作者
周柯岩
刘红梅
张颜
张金超
王书香
杨瑜涛
Keyan Zhou;Hongmei Liu;Yan Zhang;Jinchao Zhang;Shuxiang Wang;Yutao Yang(Key Laboratory of Medicinal Chemistry and Molecular Diagnosis,Key Laboratory of Chemical Biology of Hebei Province,College of Chemistry&Environmental Science,Hebei University,Baoding 071002,China)
出处
《中国科学：化学》
CAS
CSCD
北大核心
2021年第9期1269-1275,共7页
SCIENTIA SINICA Chimica
基金
国家自然科学基金(编号:21807021)
河北省自然科学基金(编号:B2020201074)资助项目。
关键词
荧光探针
生物硫醇
色烯
fluorescent probe
biothiol
chromene
