Dual emission channels for sensitive discrimination of Cys/Hcy and GSH in plasma and cells

Zhang, Yuanlin; Shao, Xiangmin; Wang, Yue; Pan, Fuchao; Kang, Ruixue; Peng, Fangfang; Huang, Zhentao; Zhang, Weijuan; Zhao, Weili

doi:10.1039/c4cc08687b

Cited by 161 publications

(74 citation statements)

References 52 publications

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“…We incorporated the phenylmercapto group into the meso position of the BODIPY core to construct fluorescent probe 82 (Figure20) [112] for the discrimination of GSH from Cys/Hcy.T he detection ability of probe 82 was similar to the before-mentioned of probe 72.T hen, we sought to examine the recognition/leaving group effect in as terically congested environment by using variousN -, O-, or S-aryl substituents with variable electronic naturesa sr ecognition groups,w hich were grafted to the meso position of the 1,3,5,7tetramethyl BODIPY dye to endow the leavinga bility ( Figure 20). [113] By screening this series of dyes (83), we obtained two appropriate probes 83-S-a and 83-O-f for the purpose of biothiol recognition.W hen the probesr eactedw ith Cys and GSH they produced two distinct fluorescence signals to differentiate between each thiol, in accordance with the earlier observations.…”

Section: Selectivep Robes For Cysmentioning

confidence: 99%

BODIPY‐Based Fluorescent Probes for Biothiols

Zhang

Wang

et al. 2020

Chemistry A European J

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190

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Fluorescent probes for biothiols have aroused increasing interest owing to their potential to enable better understanding of the diverse physiological and pathological processes related to the biothiol species. BODIPY fluorophores exhibit excellent optical properties, which can be readily tailored by introducing diverse functional units at various positions of the BODIPY core. In the present review, the development of fluorescent probes based on BODIPYs for the detection of biothiols are systematically summarized, with emphasis on the preferable detection of individual biothiols, as well as simultaneous discrimination among cysteine (Cys), homocysteine (Hcy), reduced glutathione (GSH). In addition, organelle‐targeting probes for biothiols are also highlighted. The general design principles, various recognition mechanisms, and biological applications are elaboratively discussed, which could provide a useful reference to researchers worldwide interested in this area.

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Section: Selectivep Robes For Cysmentioning

confidence: 99%

BODIPY‐Based Fluorescent Probes for Biothiols

Zhang

Wang

et al. 2020

Chemistry A European J

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190

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“…Zhang et al (32) presented a new selective fluorescent and colorimetric chemosensor for the detection of GSH. The probe could discriminate GSH from Cys and Hcy through two emission channel detection systems and the detection limit of probe for GSH reached 10 nM (3 ppb).…”

Section: Introductionmentioning

confidence: 99%

Rhodol‐based far‐red fluorescent probe for the detection of cysteine and homocysteine over glutathione

et al. 2016

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The simultaneous discrimination of cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) is of great importance due to their roles in biology and close link to many diseases, especially via the development of a far-red fluorescent probe that could be used for rapid, selective, and sensitive detection of all three. Herein, we report the characterization of a far-red fluorescent probe with turn-on fluorescence properties and visible color changes that could be used for the detection of cysteine and homocysteine over glutathione. In this study we found that the sensor could discriminate cysteine and homocysteine over glutathione within 20 min. Function of this probe was based on the conjugate addition-cyclization reaction and showed a low detection limit to cysteine and homocysteine. Upon the addition of cysteine and homocysteine, the absorption band at 592 nm rose gradually and fluorescence was detected at 645 nm. The color changed from colorless to blue and fluorescence changed from absent to strong red fluorescence, which could be differentiated by the naked eye. All these unique features make this probe particularly potentially favorable for use in cysteine/homocysteine sensing and bioimaging applications. Copyright © 2016 John Wiley & Sons, Ltd.

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“…For example, Cys and Hcy are the crucial biomolecules required for cellular growth in living organisms, and GSH is the most abundant biothiol to play a key role in redox homeostasis . For Cys, deficiency of this amino acid inside the body is associated with many diseases, such as slow growth, hair depigmentation, edema, lethargy, liver damage, loss of muscle and fat, skin lesions, and weakness . Abnormal levels of Hcy are related to disorders including cardiovascular disease and Alzheimer's disease .…”

Section: Introductionmentioning

confidence: 99%

“…[4] For Cys, deficiency of this amino acid inside the body is associated with many diseases, such as slow growth, hair depigmentation,e dema, lethargy,l iver damage, loss of muscle and fat, skin lesions,a nd weakness. [5] Abnormall evels of Hcy are relatedt od isorders includingc ardiovascular disease and Alzheimer's disease. [4b] Although GSH serves as an important biomoleculei nm aintaining the intracellular redox activities and signal transduction, alterations in its level are implicated with liver damage, HIV infection, cancer, leucocytes loss, and psoriasis.…”

Section: Introductionmentioning

confidence: 99%

Iridium(III) Complex‐Based Activatable Probe for Phosphorescent/Time‐Gated Luminescent Sensing and Imaging of Cysteine in Mitochondria of Live Cells and Animals

Zhang

Song

et al. 2019

Chemistry A European J

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This study reports an activatable iridium(III) complex probe for phosphorescence/time‐gated luminescence detection of cysteine (Cys) in vitro and in vivo. The probe, [Ir(ppy)2(NTY‐bpy)](PF6) [ppy: 2‐phenylpyridine; NTY‐bpy: 4‐methyl‐4′‐(2‐nitrovinyl)‐2,2′‐bipyridine], is developed by incorporating a strong electron‐withdrawing group, nitroolefin, into a bipyridine ligand of the IrIII complex. The luminescence of the probe is quenched owing to the intramolecular charge transfer (ICT) process, but switched on by a specific recognition reaction between the probe and Cys. [Ir(ppy)2(NTY‐bpy)](PF6) shows high sensitivity and selectivity for Cys detection and good biocompatibility. The long‐lived emission of [Ir(ppy)2(NTY‐bpy)](PF6) allows time‐gated luminescence analysis of Cys in cells and human sera. These properties make it convenient for the phosphorescence and time‐gated luminescence imaging and flow cytometry analysis of Cys in live samples. The Cys images in cancer cells and inflamed macrophage cells reveal that [Ir(ppy)2(NTY‐bpy)](PF6) is distributed in mitochondria after cellular internalization. Visualizations and flow cytometry analysis of mitochondrial Cys levels and Cys‐mediated redox activities of live cells are achieved. By using [Ir(ppy)2(NTY‐bpy)](PF6) as a probe, in vivo sensing and imaging of Cys in D. magna, zebrafish, and mice are then demonstrated.

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Dual emission channels for sensitive discrimination of Cys/Hcy and GSH in plasma and cells

Cited by 161 publications

References 52 publications

BODIPY‐Based Fluorescent Probes for Biothiols

BODIPY‐Based Fluorescent Probes for Biothiols

Rhodol‐based far‐red fluorescent probe for the detection of cysteine and homocysteine over glutathione

Iridium(III) Complex‐Based Activatable Probe for Phosphorescent/Time‐Gated Luminescent Sensing and Imaging of Cysteine in Mitochondria of Live Cells and Animals

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