An “off–on” fluorescent probe for the detection of cysteine /homocysteine and its imaging in living cells

Mengfang Tang; Luling Wu; Dan Wu; Chusen Huang; Weiping Zhu; Yufang Xu; Xuhong Qian

doi:10.1039/C6RA00832A

An “off–on” fluorescent probe for the detection of cysteine /homocysteine and its imaging in living cells†

Mengfang Tang,‡^a Luling Wu,‡^b Dan Wu,^a Chusen Huang,*^b Weiping Zhu,*^a Yufang Xu^a and Xuhong Qian^a

* Corresponding authors

^a State Key Laboratory of Bioreactor Engineering, Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China
E-mail: wpzhu@ecust.edu.cn

^b The Education Ministry Key Laboratory of Resource Chemistry, Shanghai Key Laboratory of Rare Earth Functional Materials, Department of Chemistry, College of Life and Environmental Sciences, Shanghai Normal University, 100 Guilin Road, Shanghai 200234, China
E-mail: huangcs@shnu.edu.cn

Abstract

Based on the NCL reaction, we report a novel “off–on” fluorescent probe BQ for the sensing of Cys/Hcy by a FRET strategy. Owing to the quenching effect of azo-based naphthalimide, BQ showed nonfluorescence. Upon the interaction of Cys/Hcy, a dramatic increase of the fluorescence signal was observed, with a high selectivity toward Cys/Hcy over GSH. Additionally, the discrimination of Cys from Hcy also could be achieved through the different rates of the transthioesterification reaction between thiols and BQ, especially when the concentration of Cys and Hcy was below 100 μM. The Cys/Hcy could be specifically labeled by the BODIPY fluorophore of BQ after the NCL reaction. Living cell imaging experiments demonstrated that BQ can selectively label Cys/Hcy and distinguish Cys/Hcy from other bioreagents including GSH in living systems.

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DOI: https://doi.org/10.1039/C6RA00832A
Article type: Paper
Submitted: 11 Jan 2016
Accepted: 31 Mar 2016
First published: 04 Apr 2016

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RSC Adv., 2016,6, 34996-35000

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An “off–on” fluorescent probe for the detection of cysteine /homocysteine and its imaging in living cells

M. Tang, L. Wu, D. Wu, C. Huang, W. Zhu, Y. Xu and X. Qian, RSC Adv., 2016, 6, 34996 DOI: 10.1039/C6RA00832A

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An “off–on” fluorescent probe for the detection of cysteine /homocysteine and its imaging in living cells†

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An “off–on” fluorescent probe for the detection of cysteine /homocysteine and its imaging in living cells

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