Thiol-specific fluorogenic agent for live cell non-protein thiol imaging in lysosomes

Alqahtani, Yahya S.; Wang, Shenggang; Najmi, Asim; Huang, Yue; Guan, Xiaoxu

doi:10.1007/s00216-019-02026-3

Cited by 8 publications

(10 citation statements)

References 41 publications

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“…Cellular experiments showed that BIS-MORX was able to image, quantify, and detect the change of NPSH in lysosomes in live cells. We also developed another lysosomal NPSH imaging agent TBONES (Probe 78) [207]. Interestingly, the lysosome selectivity of this probe was likely due to its selective entry of lysosomes through an endocytosis pathway which is different than other lysosome-targeting probes.…”

Section: Detection Of Lysosomal Npsh Via Snar Reactions Using Ether Thioether As a Leaving Group Detection Of Lysosomal Npsh Via Snar Reamentioning

confidence: 99%

Fluorescent Probes for Live Cell Thiol Detection

2021

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Thiols play vital and irreplaceable roles in the biological system. Abnormality of thiol levels has been linked with various diseases and biological disorders. Thiols are known to distribute unevenly and change dynamically in the biological system. Methods that can determine thiols’ concentration and distribution in live cells are in high demand. In the last two decades, fluorescent probes have emerged as a powerful tool for achieving that goal for the simplicity, high sensitivity, and capability of visualizing the analytes in live cells in a non-invasive way. They also enable the determination of intracellular distribution and dynamitic movement of thiols in the intact native environments. This review focuses on some of the major strategies/mechanisms being used for detecting GSH, Cys/Hcy, and other thiols in live cells via fluorescent probes, and how they are applied at the cellular and subcellular levels. The sensing mechanisms (for GSH and Cys/Hcy) and bio-applications of the probes are illustrated followed by a summary of probes for selectively detecting cellular and subcellular thiols.

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Section: Detection Of Lysosomal Npsh Via Snar Reactions Using Ether Thioether As a Leaving Group Detection Of Lysosomal Npsh Via Snar Reamentioning

confidence: 99%

Fluorescent Probes for Live Cell Thiol Detection

2021

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“…Selective, sensitive, and rapid sensing of thiols has attracted considerable attention in various fields ranging from the petrochemical industry , to medicine. , Intracellular thiols include cysteine (Cys; Chart ), glutathione (GSH), and homocysteine (Hcys), which play a vital role in maintaining redox homeostasis through the equilibrium between reduced thiols (RSH) and oxidized disulfides (RSSR). , They behave as free radical scavengers, radioprotective agents, cancer indicators, antitoxin, and antioxidants as well . A wealth of investigations over the decades have revealed that imbalance in the redox buffering systems caused by oxidative stress has been linked to a number of diseases, including cancer, chronic neurodegenerative diseases (e.g., Alzheimer’s), and cardiovascular disease. − …”

Section: Introductionmentioning

confidence: 99%

Syntheses of Water-Soluble Silver(II)–Phthalocyanines toward Optical Sensing for Thiol Detection

et al. 2021

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Water-soluble silver(II)–phthalocyanine complexes (AgPcs), tetrakis{4-(N-alkylpyridinium)thio}phthalocyaninato silver(II) tetrafluoroborate, [Ag(tRpySpc)](BF4)4, (R = Me and Et), have been synthesized for the first time by quaternization of pyridyl groups of tetrakis(4-pyridylthio)phthalocyaninato silver(II) by using Meerwein reagents and characterized by ESI-MS, elemental analyses, and optical absorption spectroscopy. Although they strongly aggregate in water, the presence of appropriate surfactants, such as polyethyleneglycol-monooleyl ether (n = approximately 50; PEG50) and sodium dodecyl sulfate, effectively disaggregates them to monomeric species. The spectral properties of the AgPcs and their aggregates in aqueous and nonaqueous solutions have been investigated by optical absorption, emission, and magnetic circular dichroism spectroscopy. These AgPcs rapidly react with thiols such as cysteine, glutathione, homocysteine, and sodium 2-sulfanylethanesulfonate (even on the order of 0.01 mM) in aqueous PEG50 solutions at room temperature to liberate the corresponding macrocyclic ligand, H2Pc, but not with the other amino-acid analogs without sulfhydryl groups. The molar ratio of thiol to AgPc has been determined to be 1:1. Since AgPcs are essentially nonfluorescent at room temperature, while H2Pcs emit intense red fluorescence, AgPcs can be a potent thiol-sensor toward bioimaging.

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“…Recently, we reported TBONES (Figure ) as a thiol specific lysosome selective fluorogenic agent . The reagent was initially designed to image cell surface thiols but failed.…”

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confidence: 99%

“…Recently, we reported TBONES (Figure 1) as a thiol specific lysosome selective fluorogenic agent. 36 The reagent was initially designed to image cell surface thiols but failed. Instead, the reagent was found to image selectively NPSH in lysosomes through possibly an endocytosis mechanism.…”

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confidence: 99%

“…One of the disadvantages of TBONES in imaging NPSH in lysosomes in live cells was the length of the time; it took 12 h to image lysosomal NPSH at 400 μM. Also, the excitation and emission wavelengths of thiol adducts derived from cysteine and homocysteine are 40 nm different from those of other NPSHs due to an intramolecular rearrangement reaction of these two amino acids, 36 which complicate the imaging and quantification of NPSH in live cells.…”

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Design, Synthesis, and Characterization of Bis(7-(N-(2-morpholinoethyl)sulfamoyl)benzo[c][1,2,5]oxadiazol-5-yl)sulfane for Nonprotein Thiol Imaging in Lysosomes in Live Cells

et al. 2019

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Thiols are critical to cellular structures and functions. Disturbance of cellular thiols has been found to affect cell functions and cause various diseases. Intracellularly, thiols were found unevenly distributed in subcellular organelles. Probes capable of detecting subcellular thiol density in live cells are valuable tools in determining thiols’ roles at the subcellular level. The subcellular organelle lysosome is the place where unwanted macromolecules are removed through degradation by hydrolytic enzymes. The degradation also serves as a regulation of a variety of cellular functions such as autophagy, endocytosis, and phagocytosis to maintain cellular homeostasis. Thiols are found to be involved in the lysosomal degradation process. A probe that can detect lysosomal thiols in live cells will be a valuable tool in unveiling the roles of thiols in lysosomes. We would like to report bis(7-(N-(2-morpholinoethyl)sulfamoyl)benzo[c][1,2,5]-oxadiazol-5-yl)sulfane (BISMORX) as a thiol specific fluorogenic agent for live cell nonprotein thiol (NPSH) imaging in lysosomes through fluorescence microscopy. BISMORX itself shows no fluorescence and reacts readily with a NPSH to form a fluorescent thiol adduct with excitation and emission wavelengths of 380 and 540 nm, respectively. BISMORX does not react with compounds containing nucleophilic functional groups other than thiols such as −OH, −NH2, and −COOH. No reaction was observed either when BISMORX was mixed with protein thiols. BISMORX was able to image, quantify, and detect the change of NPSH in lysosomes in live cells. A colocalization experiment with LysoTracker Red DND-99 confirmed that the thiols imaged by BISMORX were indeed lysosomal thiols.

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Thiol-specific fluorogenic agent for live cell non-protein thiol imaging in lysosomes

Cited by 8 publications

References 41 publications

Fluorescent Probes for Live Cell Thiol Detection

Fluorescent Probes for Live Cell Thiol Detection

Syntheses of Water-Soluble Silver(II)–Phthalocyanines toward Optical Sensing for Thiol Detection

Design, Synthesis, and Characterization of Bis(7-(N-(2-morpholinoethyl)sulfamoyl)benzo[c][1,2,5]oxadiazol-5-yl)sulfane for Nonprotein Thiol Imaging in Lysosomes in Live Cells

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