A Pyrene-Based Fluorescent Probe for Specific Detection of Cysteine and its Application in Living Cell

Chao, Jianbin; Wang, Zhuo; Zhang, Yongbin; Huo, Fangjun; Yin, Caixia; Li, Ming; Duan, Yuexiang

doi:10.1007/s10895-021-02703-6

Cited by 9 publications

(3 citation statements)

References 41 publications

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“…In recent years, research on fluorescent probes has made phenomenal headway. A large number of fluorescent sensors for distinguishing biothiols over other amino acids have been reported, and are mainly based on different reactions, including cyclization of aldehydes, cleavage of sulfonamides, cleavage of disulfides, the Michael addition reaction and the intramolecular elimination reaction [19][20][21][22][23][24][25]. As far as we know, the vast majority of organic small-molecule fluorescence probes need to overcome a variety of defects in performance, such as strict test conditions, long response times, low sensitivity and selectivity, shorter-emission wavelengths, and high biotoxicity [26][27][28], which limit the further application of these fluorescent probes for the detection of various biomarkers in complex biological environments.…”

Section: Introductionmentioning

confidence: 99%

Bioimaging and Sensing Thiols In Vivo and in Tumor Tissues Based on a Near-Infrared Fluorescent Probe with Large Stokes Shift

Yan

Hou

et al. 2023

Molecules

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The well-known small-molecule biothiols have been used to maintain the normal metabolism of peroxy radicals, forming protein structures, resisting cell apoptosis, regulating metabolism, and protecting the homeostasis of cells in the organism. A large amount of research has found that abnormal levels of the above biothiols can cause some adverse diseases, such as changes in hair pigmentation, a slower growth rate, delayed response, excessive sleep and skin diseases. In order to further investigate the exact intracellular molecular mechanism of biothiols, it is imperative to explore effective strategies for real-time biothiol detection in living systems. In this work, a new near-infrared (NIR) emission fluorescence probe (probe 1) for sensitive and selective detection of biothiols was devised by combining dicyanoisophorone derivatives with the dinitrobenzenesulfonyl (DNBS) group. As expected, probe 1 could specifically detect biothiols (Cys, Hcy and GSH) through the dinitrobenzenesulfonyl group to form dye 2, which works as a signaling molecule for sensing biothiols in real samples. Surprisingly, probe 1 showed superior sensing characteristics and low-limit detection towards biothiols (36.0 nM for Cys, 39.0 nM for Hcy and 48.0 nM for GSH) with a large Stokes shift (134 nm). Additionally, the function of probe 1 as a platform for detecting biothiols was confirmed by confocal fluorescence imaging of biothiols in MCF-7 cells and zebrafish. More importantly, the capability of probe 1 in vivo has been further evaluated by imaging the overexpressed biothiols in tumor tissue. It is reasonable to believe that probe 1 can provide a valuable method to explore the relationship between biothiols and the genesis of tumor.

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Section: Introductionmentioning

confidence: 99%

Bioimaging and Sensing Thiols In Vivo and in Tumor Tissues Based on a Near-Infrared Fluorescent Probe with Large Stokes Shift

Yan

Hou

et al. 2023

Molecules

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“…Compared with common analysis methods such as fluorescent spectroscopy, potentiometry, and high performance liquid chromatography (HPLC), 9,[12][13][14][15][16][17][18] which are cumbersome and less used for the intracellular detection of biological thiols, fluorescent probes have attracted increasing attention in this field because of their simple operation, high resolution, high sensitivity, real-time detection, penetrability and noninvasiveness. [19][20][21][22][23][24][25][26] At present, more and more small molecule fluorescent probes and nanosensors have been designed, synthesized, and extensively used in the detection of biological thiols.…”

Section: Introductionmentioning

confidence: 99%

A ratiometric fluorescent probe based on two-isophorone fluorophore for detecting cysteine

Zhang

Jiang

et al. 2022

J. Mater. Chem. B

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“…The chemosensor comprises a signal unit and an identification unit, the former is used for selective binding with target molecules, while the latter shows this binding through specific signal forms. The design idea of our chemosensor is as follows: 1) Pyrene is used as the signal element in view of its excellent photophysical properties and easy modification on the molecular structure [11,12]. Meanwhile, construction of C=N isomerization by Schiff base reaction has been used as the recognition mechanism in photophysical process because it is easy to design "offon" chemosensors by some simple organic preparations.…”

Section: Introductionmentioning

confidence: 99%

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2022

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It is of great significance to find a suitable method to detect Fe 3+ due to its essential role in human and animal health. Artificial chemosensors have been a suitable method in view of simple preparation, fast response, et al. [Aim]: A selective Fe 3+ chemosensor was designed. [Method]: A novel Fe 3+ -selective chemosensor was rationally designed based on pyrene derivative by the introduction of benzoyl hydrazine. [Results] The proposed chemosensor presented the good selectivity for Fe 3+ in prescence of other common metal ions. [Conclusions]: The proposed idea can be used for reference to enrich chemosensors.

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A Pyrene-Based Fluorescent Probe for Specific Detection of Cysteine and its Application in Living Cell

Cited by 9 publications

References 41 publications

Bioimaging and Sensing Thiols In Vivo and in Tumor Tissues Based on a Near-Infrared Fluorescent Probe with Large Stokes Shift

Bioimaging and Sensing Thiols In Vivo and in Tumor Tissues Based on a Near-Infrared Fluorescent Probe with Large Stokes Shift

A ratiometric fluorescent probe based on two-isophorone fluorophore for detecting cysteine

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