Benzoxazine-based fluorescent probes with different auxochrome groups for cysteine detection

Yang, Xiu-Zhi; Wei, Xue-Rui; Sun, Rong; Xu, Yu-Jie; Ge, Jian‐Feng

doi:10.1016/j.saa.2019.117582

Cited by 16 publications

(4 citation statements)

References 45 publications

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“…The reaction mechanism of fluorescent probes based on acrylic acid phenyl esters for detecting biological thiols has been extensively studied [26][27][28][29][30][31][32][33][54][55][56][57][58][59][60]. The reaction involves two steps: first, the Michael addition of thiols to the probe's double bond leads to the formation of linear thioethers.…”

Section: The Reaction Mechanism Of Aza-acryl With the Thiolsmentioning

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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Section: The Reaction Mechanism Of Aza-acryl With the Thiolsmentioning

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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“…Fluorescent probes have the advantages of simple preparation, reliability, rapidity, low detection limit, multi-channel, high-throughput, low cost, small light damage, high sensitivity and real-time monitoring, and are widely used in the fields of biological detection and fluorescent imaging [2,7,8]. There are many reports in the literature that the detection range of Cys based on fluorescence sensor is µM, with a detection limit range of approximately 0.02-0.2 µM, and a Stokes shift of approximately 50-140 nm, which can be effectively applied to the detection of a low concentration of Cys [9][10][11][12][13][14][15][16][17][18]. Although many fluorescent probes have made a significant contribution to the detection of Cys, there are still many problems to be solved.…”

Section: Introductionmentioning

confidence: 99%

2-Mercaptobenzimidazole Functionalized Copper Nanoparticles Fluorescence Probe for Sensitivity and Selectivity Detection of Cys in Serum

Liu

Dou

Zhang

2023

Sensors

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In this paper, a 2-mercaptobenzimidazole-copper nanoparticles (MBI-CuNPs) fluorescent probe with high performance based on 2-mercaptobenzimidazole functionalized copper nanoparticles was synthesized by a hydrothermal method and used for cysteine (Cys) detection in serum. The MBI-CuNPs probe exhibits strong fluorescence emission at 415 nm under the excitation at 200 nm, which is attributed to the metal-ligand charge transfer (MLCT) transition through the coordination of an MBI ligand and monovalent copper. Furthermore, the MBI-CuNPs probe has a high quenching fluorescence response to Cys, and shows a good linearity relationship with Cys in 0.05–65 µM, with a detection limit of 52 nM. Moreover, the MBI-CuNPs probe could eliminate the interference of biological mercaptan Hcy and GSH with a similar structure and reaction properties, due to the strong electron-donating ability of Cys, which can quench the fluorescence of the MBI-CuNPs probe. The MBI-CuNPs probe was applied to the analysis of Cys in real serum, and the absolute recovery rate was as high as 90.23–97.00%. Such a fluorescent probe with high sensitivity and selectivity has potential applications for the early prevention of various diseases caused by abnormal Cys levels.

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“…To date, a lot of colorimetric and fluorescent probes for biothiols have been developed [ 36 , 37 , 38 , 39 , 40 ]. Latterly, scientists have begun to design new fluorescent probes based on Nile-red fluorophore for detecting biothiols, and several good probes have been reported [ 41 , 42 , 43 , 44 ]. Cui’s group developed a fluorescent probe based on Nile-red for H 2 S detection [ 43 ].…”

Section: Introductionmentioning

confidence: 99%

“…The probe exhibits a high sensitivity and selectivity for H 2 S when compared with other small biothiols. Using acrylate group as a reaction site, Ge’s group constructs two NR-based probes for Cys detection [ 44 ]. In selectivity experiments, it is found that Hcy and GSH displayed slight fluorescence enhancement, and Cys could induce a remarkable enhancement.…”

Section: Introductionmentioning

confidence: 99%

Nile-Red-Based Fluorescence Probe for Selective Detection of Biothiols, Computational Study, and Application in Cell Imaging

Xiang

Yan

et al. 2020

Molecules

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A new colorimetric and fluorescence probe NRSH based on Nile-red chromophore for the detection of biothiols has been developed, exhibiting high selectivity towards biothiols over other interfering species. NRSH shows a blue shift in absorption peak upon reacting with biothiols, from 587 nm to 567 nm, which induces an obvious color change from blue to pink and exhibits a 35-fold fluorescence enhancement at 645 nm in red emission range. NRSH displays rapid (<1 min) response for H2S, which is faster than other biothiols (>5 min). The detection limits of probe NRSH towards biothiols are very low (22.05 nM for H2S, 34.04 nM for Cys, 107.28 nM for GSH and 113.65 nM for Hcy). Furthermore, NRSH is low cytotoxic and can be successfully applied as a bioimaging tool for real-time monitoring biothiols in HeLa cells. In addition, fluorescence mechanism of probe NRSH is further understood by theoretical calculations.

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Benzoxazine-based fluorescent probes with different auxochrome groups for cysteine detection

Cited by 16 publications

References 45 publications

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

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

2-Mercaptobenzimidazole Functionalized Copper Nanoparticles Fluorescence Probe for Sensitivity and Selectivity Detection of Cys in Serum

Nile-Red-Based Fluorescence Probe for Selective Detection of Biothiols, Computational Study, and Application in Cell Imaging

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