Three asymmetric BODIPY derivatives as fluorescent probes for highly selective and sensitive detection of cysteine in living cells

被引：5

作者：

Yue, Jinlei ^{[1
]}

Wang, Nannan ^{[1
]}

Wang, Jiamin ^{[1
,3
]}

Tao, Yuanfang ^{[1
]}

Wang, Han ^{[1
]}

Liu, Jinying ^{[1
]}

Zhang, Jian ^{[1
]}

Jiao, Junrong ^{[1
]}

Zhao, Weili ^{[1
,2
]}

机构：

[1] Henan Univ, Sch Mat Sci & Engn, Minist Educ, Key Lab Special Funct Mat, Kaifing 475004, Peoples R China

[2] Fudan Univ, Inst Integrat Med, Sch Pharm, Shanghai 201203, Peoples R China

[3] Henan Univ, Key Lab Nat Med & Immunoengn Henan Prov, Kaifeng 475004, Peoples R China

来源：

ANALYTICAL METHODS | 2021年 / 13卷 / 26期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

TURN-ON PROBE; HUMAN PLASMA; HOMOCYSTEINE; CYS; NBD; CHEMISTRY; THIOLS; DYES;

D O I：

10.1039/d1ay00740h

中图分类号：

O65 [分析化学];

学科分类号：

070302 ; 081704 ;

摘要：

Biothiols are widely involved in various important physiological activities and play a significant role in maintaining redox homeostasis in living organisms. Herein, we designed and synthesized three new asymmetric fluorescent probes (BDP-S-Ph, BDP-S-ENE and BDP-S-R) to discriminate Cys from Hcy/GSH. These probes reacted with Cys to form meso-amino-BODIPYs via SNAr substitution-rearrangement, thereby inducing a fluorescence turn-on effect. Moreover, they could selectively and sensitively detect Cys in solution with low detection limits (50 nM, 28 nM and 87 nM, respectively). Through comparing the response rates of the three probes to Cys, we concluded that the increase of conformational restrictions led to a decrease in probe reactivity. Besides, the sensing mechanism was demonstrated by mass spectrometry. Furthermore, cell experiments indicated that the probes were able to image exogenous and endogenous Cys through green or red channels in living cells.

引用

页码：2908 / 2914

页数：8

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[1] Betaine attenuates Alzheimer-like pathological changes and memory deficits induced by homocysteine [J].