Recent Progress in the Rational Design of Biothiol-Responsive Fluorescent Probes

Xie, Wenzhi; Jiang, Jinyu; Shu, Dunji; Zhang, Yanjun; Yang, Sheng; Zhang, Kai

doi:10.3390/molecules28104252

Cited by 15 publications

(3 citation statements)

References 106 publications

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“…Additionally, the study introduces a logic gate based on the 1O probe that utilizes the probe's color and fluorescence changes to perform logical operations, paving the way for the development of innovative biosensors. Thiol small molecules, including biothiols such as cysteine, homocysteine, and glutathione, as well as industrial thiophenols, are crucial for both biological systems and industrial applications [207][208][209][210][211][212]. Inside living organisms, these thiol compounds mainly act as antioxidants to maintain cellular redox balance and participate in various biochemical reactions; accurate detection of these compounds can help study cellular responses to disease and stress.…”

Section: Thiolsmentioning

confidence: 99%

“…Thiol small molecules, including biothiols such as cysteine, homocysteine, and glutathione, as well as industrial thiophenols, are crucial for both biological systems and industrial applications [ 207 , 208 , 209 , 210 , 211 , 212 ]. Inside living organisms, these thiol compounds mainly act as antioxidants to maintain cellular redox balance and participate in various biochemical reactions; accurate detection of these compounds can help study cellular responses to disease and stress.…”

Section: Applications Of Photoswitchable Fluorescent and Colorimetric...mentioning

confidence: 99%

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Recent Advances in Photoswitchable Fluorescent and Colorimetric Probes

Chen,

Tang,

Yang

et al. 2024

Molecules

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In recent years, significant advancements have been made in the research of photoswitchable probes. These probes undergo reversible structural and electronic changes upon light exposure, thus exhibiting vast potential in molecular detection, biological imaging, material science, and information storage. Through precisely engineered molecular structures, the photoswitchable probes can toggle between “on” and “off” states at specific wavelengths, enabling highly sensitive and selective detection of targeted analytes. This review systematically presents photoswitchable fluorescent and colorimetric probes built on various molecular photoswitches, primarily focusing on the types involving photoswitching in their detection and/or signal response processes. It begins with an analysis of various molecular photoswitches, including their photophysical properties, photoisomerization and photochromic mechanisms, and fundamental design concepts for constructing photoswitchable probes. The article then elaborates on the applications of these probes in detecting diverse targets, including cations, anions, small molecules, and biomacromolecules. Finally, it offers perspectives on the current state and future development of photoswitchable probes. This review aims to provide a clear introduction for researchers in the field and guidance for the design and application of new, efficient fluorescent and colorimetric probes.

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Section: Thiolsmentioning

confidence: 99%

Section: Applications Of Photoswitchable Fluorescent and Colorimetric...mentioning

confidence: 99%

Recent Advances in Photoswitchable Fluorescent and Colorimetric Probes

Chen,

Tang,

Yang

et al. 2024

Molecules

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“…Biothiols such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) play a crucial role in various biological reactions [1,2]. Cysteine, in particular, is an intrinsically nucleophilic amino acid found in proteins that adjust various biochemical functions [3].…”

Section: Introductionmentioning

confidence: 99%

A Novel Fluorescence Probe Based on Azamonardine for Detecting and Imaging Cysteine in Cells and Zebrafish with High Selectivity and Sensitivity

Zhao,

Wang,

Abdulkhaleq

et al. 2023

Molecules

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A novel fluorescent probe based on azamonardine (Aza) fluorophore was designed and synthesized for the highly selective detection of cysteine (Cys) in vivo and in vitro. After reacting with acryloyl chloride, the fluorescence of Aza is effectively quenched, resulting in the formation of the Aza-acryl probe. Upon the addition of Cys, the ester bond of Aza-acryl is cleaved, releasing a new compound (Compound 1) with strong fluorescence, thereby achieving fluorescence turn-on detection of Cys. The structure of Aza-acryl was characterized using X-ray crystallography and NMR spectroscopy. Additionally, density functional theory was employed to elucidate the quenching mechanism of the acyl group on the Aza. Aza-acryl exhibits high selectivity towards Cys and distinguishes it from other biothiols such as homocysteine (Hcy) and glutathione (GSH). The mechanism of Aza-acryl for detecting Cys was investigated through HPLC, NMR spectroscopy, high-resolution mass spectrometry, and reaction kinetics experiments. Aza-acryl demonstrates excellent imaging capabilities for Cys in cells and zebrafish, providing a reliable and selectable tool for the detection and imaging of Cys in biological systems.

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Glutathione‐responsive Aggregation‐induced Emission Photosensitizers for Enhanced Photodynamic Therapy of Lung Cancer

Sun,

Chen,

Lam

et al. 2024

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Lung cancer, a highly prevalent and lethal form of cancer, is often associated with oxidative stress. Photodynamic therapy (PDT) has emerged as a promising alternative therapeutic tool in cancer treatments, but its efficacy is closely correlated to the photosensitizers generating reactive oxygen species (ROS) and the antioxidant capacity of tumor cells. In particular, glutathione (GSH) can reduce the ROS and thus compromise PDT efficacy. In this study, a GSH‐responsive near‐infrared photosensitizer (TBPPN) based on aggregation‐induced emission for real‐time monitoring of GSH levels and enhanced PDT for lung cancer treatment is developed. The strategic design of TBPPN, consisting of a donor–acceptor structure and incorporation of dinitrobenzene, enables dual functionality by not only the fluorescence being activated by GSH but also depleting GSH to enhance the cytotoxic effect of PDT. TBPPN demonstrates synergistic PDT efficacy in vitro against A549 lung cancer cells by specifically targeting different cellular compartments and depleting intracellular GSH. In vivo studies further confirm that TBPPN can effectively inhibit tumor growth in a mouse model with lung cancer, highlighting its potential as an integrated agent for the diagnosis and treatment of lung cancer. This approach enhances the effectiveness of PDT for lung cancer and deserves further exploration of its potential for clinical application.

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Recent Progress in the Rational Design of Biothiol-Responsive Fluorescent Probes

Cited by 15 publications

References 106 publications

Recent Advances in Photoswitchable Fluorescent and Colorimetric Probes

Recent Advances in Photoswitchable Fluorescent and Colorimetric Probes

A Novel Fluorescence Probe Based on Azamonardine for Detecting and Imaging Cysteine in Cells and Zebrafish with High Selectivity and Sensitivity

Glutathione‐responsive Aggregation‐induced Emission Photosensitizers for Enhanced Photodynamic Therapy of Lung Cancer

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