A novel near-infrared fluorescent probe for intracellular detection of cysteine
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RESEARCH PAPER
A novel near-infrared fluorescent probe for intracellular detection of cysteine Lihe Zhao 1 & Xu He 2 & Yibing Huang 2 & Siqi Zhang 1 & Hao Han 1 & Lanlan Xu 1 & Xinghua Wang 1 & Daqian Song 1 & Pinyi Ma 1 & Ying Sun 1 Received: 11 June 2020 / Revised: 23 July 2020 / Accepted: 29 July 2020 # Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract Cysteine (Cys) takes part in redox balance in cells as an antioxidant, and imbalance of Cys content in the body can cause a variety of diseases. It is very important to develop a new fluorescent chemosensor to specifically detect Cys intracellular. In this work, a novel NIR fluorescent probe was constructed based on 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indol-3-ium iodide and 5-(4hydroxyphenyl)furan-2-carbaldehyde. The probe could selectively detect Cys in the presence of homocysteine (Hcy), glutathione (GSH), and other interferences. It also had a number of advantages, including nucleolus-targeting ability, long fluorescence emission wavelength (685 nm), low detection limit (56 nM), and large Stokes shift (172 nm). The probe was employed to enable visualization of Cys in HepG2 cells, and due to its good response in viscous environment, the probe could also locate nucleoli intracellular. Keywords Fluorescent probe . Cysteine . Nucleolus located . Near-infrared . Living cells
Introduction There are many sulfhydryl-containing amino acids in organisms, such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) [1, 2]. Cys plays a key role for maintaining the homeostasis of the redox balance [3, 4]; thus, imbalance of Cys content can lead to a variety of diseases [5]. Whereas the lack of Cys can cause hair depigmentation, slow growth, liver damage, and so on, too high content of Cys can lead to neuropathic poisoning [6–8]. A number of methods, such as UV-Vis absorption spectrophotometry, high-performance liquid chromatography Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00216-020-02853-9) contains supplementary material, which is available to authorized users. * Pinyi Ma [email protected] * Ying Sun [email protected] 1
College of Chemistry, Jilin University, Qianjin Street 2699, Changchun 130012, Jilin, China
2
College of Life Sciences, Jilin University, Qianjin Street 2699, Changchun 130012, Jilin, China
(HPLC) tandem mass spectrometry (HPLC/MS), HPLC, and fluorescent spectrometry, have been developed to detect biothiols [9–13]. Because the intracellular environment of living cell is highly complex, only a few of these methods are effective when use in organisms. The concentration of Cys in the cell is 1–10 mM and that of GSH is 30–200 μM. This requires the probe to have good anti-interference ability [14, 15]. Owing to its advantages, such as real-time detection, good biocompatibility, and noninvasiveness, fluorescent spectrometry has become a valuable method for detection of Cys [16–19]. Near-infrared (NIR) fluorescent dyes have received high attention due to their excellent cell penet
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