Thiol nucleophilic reactions and their applications in thiol fluorescent recognition

Yin, Caixia; Huo, Fangjun; Yue, Yongkang

doi:10.1360/n032016-00138

Sci. Sin.-Chim

2017

DOI: 10.1360/n032016-00138

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Thiol nucleophilic reactions and their applications in thiol fluorescent recognition

Caixia Yin¹,

Fangjun Huo²,

Yongkang Yue³

Abstract: Because of the physiology and pathology importance of bio-thiols, more and more scientists devoted to visualize the biological processes induced by bio-thiols. Fluorescent probes as one of the most attractive tools have been widely developed for thiols specific detection and imaging because of the nonintrusive nature. Based on the thiol nucleophilic reaction, we herein summarized the designing strategies and the optical properties of the thiols probes developed by our group in recent years. Further, we discuss… Show more

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Cited by 3 publications

References 37 publications

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Thiol “Click” Chromene Ring Opening and Subsequent Cascade Nucleophilic Cyclization NIR Fluorescence Imaging Reveal High Levels of Thiol in Drug-Resistant Cells

Zhao

Yue

et al. 2020

Anal. Chem.

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As the structural unit of natural products, chromene derivatives show a wide range of biological activity and pharmacological activity due to their unique photophysical and chemical properties. Ten years ago, our research group discovered the "thiol-chromene" click reaction, which achieved the selective detection of thiols through the change of the optical spectrum. Afterward, we attempted to develop various chromene-based fluorescent probes for imaging including near-infrared (NIR) probe, ratiometric probe, and multifunctional probe. However, how to integrate the fluorophore and reaction sites into the chromenebased skeleton remains challenging. In this work, we connected the chromene motif with the NIR fluorophore methylene blue utilizing a carbamate spacer to provide a new fluorescent probe (CM-NIR), which is triggered by thiols to open the pyran ring followed by attacking the carbamate by phenolate to releases the methylene blue. This novel cascade mechanism avoids the formation of paraquinone methides, which proved to be toxic to normal cells. CM-NIR also showed the specific imaging of thiols in living cells and mice. More importantly, the thiols level in drug-resistant cancer cells was found to be significantly higher than that in the corresponding cancer cell, which indicated that the thiols level may have an important role in cancer cells developing drug resistance.

show abstract

Thiol “Click” Chromene Ring Opening and Subsequent Cascade Nucleophilic Cyclization NIR Fluorescence Imaging Reveal High Levels of Thiol in Drug-Resistant Cells

Zhao

Yue

et al. 2020

Anal. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

A novel fluorescent probe with a large Stokes shift for colorimetric and selective detection of cysteine in water, milk, cucumber, pear and tomato

Luo,

Guo,

Wang

et al. 2024

Anal. Methods

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Chromene-based fluorescent probes for sensing and bioimaging

Zhao

Yue

et al. 2022

Chemical Physics Reviews

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Chromene is an important motif in natural products and is the backbone for a range of fluorescent molecules. Chromene derivatives are particularly important for biological applications because of their distinctive photophysical and chemical properties. Recent research efforts have been focused on utilizing chromene-based probes motif for biological sensing applications. Most notably, the “thiol-chromene” click reaction realized the selective and rapid recognition of thiols. This Review presents the various chromene-based probes for a range of biologically relevant analytes. This includes examples of sensors for thiols, amino acids, hydrogen peroxide, and nitroreductase, as well as subcellular organelle-targeted probes.

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Thiol nucleophilic reactions and their applications in thiol fluorescent recognition

Cited by 3 publications

References 37 publications

Thiol “Click” Chromene Ring Opening and Subsequent Cascade Nucleophilic Cyclization NIR Fluorescence Imaging Reveal High Levels of Thiol in Drug-Resistant Cells

Thiol “Click” Chromene Ring Opening and Subsequent Cascade Nucleophilic Cyclization NIR Fluorescence Imaging Reveal High Levels of Thiol in Drug-Resistant Cells

A novel fluorescent probe with a large Stokes shift for colorimetric and selective detection of cysteine in water, milk, cucumber, pear and tomato

Chromene-based fluorescent probes for sensing and bioimaging

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