Synthesis of a Flavone Based Fluorescent Probe Bearing a Nitroolefin Moiety for Selective Detection of Cysteine

In this paper, we report the synthesis, characterization and investigation of the optical properties of a new fluorescent probe, 4ʹ-nitroolefinylflavone (4ʹ-NOF) 1, based on a flavone skeleton and bearing a nitroolefin moiety. Upon the addition of cysteine, a remarkable fluorescence enhancement (200 fold) was observed for probe 1 accompanied with a slight blue shift from 457 nm to 459 nm. The prepared probe displays high selectivity and sensitivity towards cysteine over other amino acids. The Michael addition of cysteine to probe 1 was confirmed by 1H-NMR spectroscopy. The detection limit of probe 1 towards cysteine was found to be 1.63 μΜ, a lower concentration than the normal human cysteine level, 30-200 μΜ.

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

Molecules ◽

10.3390/molecules25204718 ◽

2020 ◽

Vol 25 (20) ◽

pp. 4718

Author(s):

Xiang Rong ◽

Zhong-Yong Xu ◽

Jin-Wu Yan ◽

Zhi-Zhong Meng ◽

Bin Zhu ◽

...

Keyword(s):

Cell Imaging ◽

High Selectivity ◽

Fluorescence Enhancement ◽

Fluorescence Probe ◽

Color Change ◽

Computational Study ◽

Theoretical Calculations ◽

Nile Red ◽

Blue Shift ◽

Selective Detection

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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Rational modulation of coumarin–hemicyanine platform based on OH substitution for higher selective detection of hypochlorite

Chemical Communications ◽

10.1039/c9cc06477j ◽

2020 ◽

Vol 56 (8) ◽

pp. 1219-1222 ◽

Cited By ~ 11

Author(s):

Jin-Shuai Lan ◽

Li Liu ◽

Rui-Feng Zeng ◽

Yan-Hong Qin ◽

Yun Liu ◽

...

Keyword(s):

Fluorescent Probe ◽

High Selectivity ◽

Selective Detection ◽

Ratiometric Fluorescent Probe

A NIR and ratiometric fluorescent probe was developed to quantitate arthritis-dependent HOCl production in vivo with high selectivity and sensitivity.

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A novel rhodamine-based fluorescent probe for selective detection of ClO– and its application in living cell imaging

Canadian Journal of Chemistry ◽

10.1139/cjc-2018-0123 ◽

2018 ◽

Vol 96 (12) ◽

pp. 1129-1133

Author(s):

Changping Yang ◽

Mingliang Zuo ◽

Xiaoli Hu ◽

Xuelin Chen ◽

Duoduo Zhang ◽

...

Keyword(s):

Aqueous Solution ◽

Cell Imaging ◽

High Selectivity ◽

Fluorescence Enhancement ◽

Colour Change ◽

Living Cells ◽

Fluorescent Imaging ◽

Selective Detection ◽

Living Cell Imaging ◽

Interfering Ions

A novel fluorescent rhodamine-based probe L for selective responding to ClO– has been synthesized and characterized. The spectroscopy showed that probe L can detect ClO– in aqueous solution without interaction with other interfering ions, and the detection is also evident by the colour change from colourless to reddish purple under white light. The remarkable fluorescence enhancement showed the high selectivity and sensitivity of probe L for the detection of ClO–. Furthermore, probe L was applied to intracellular fluorescent imaging of HeLa cells treated with ClO– and MTT assay showed nontoxicity in living cells.

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Multifunctional rhodamine B appended ROMP derived fluorescent probe detects Al3+ and selectively labels lysosomes in live cells

Scientific Reports ◽

10.1038/s41598-020-76525-0 ◽

2020 ◽

Vol 10 (1) ◽

Author(s):

Upendar Reddy Gandra ◽

Raphael Courjaret ◽

Khaled Machaca ◽

Mohammed Al-Hashimi ◽

Hassan S. Bazzi

Keyword(s):

Fluorescent Probe ◽

High Selectivity ◽

Fluorescent Sensors ◽

Live Cells ◽

Selective Detection ◽

Acidic Ph ◽

Specific Detection ◽

Polymer Backbone ◽

Sensing Applications ◽

Limit Detection

Abstract There a few reports of rhodamine-based fluorescent sensors for selective detection of only Al3+, due to the challenge of identifying a suitable ligand for binding Al3+ ion. The use of fluorophore moieties appended to a polymer backbone for sensing applications is far from mature. Here, we report a new fluorescent probe/monomer 4 and its ROMP derived polymer P for specific detection of Al3+ ions. Both monomer 4 and its polymer P exhibit high selectivity toward only Al3+ with no interference from other metal ions, having a limit detection of 0.5 and 2.1 µM, respectively. The reversible recognition of monomer 4 and P for Al3+ was also proved in presence of Na2EDTA by both UV–Vis and fluorometric titration. The experimental data indicates the behavior of 4 and P toward Al3+ is pH independent in medium conditions. In addition, the switch-on luminescence response of 4 at acidic pH (0 < 5.0), allowed us to specifically stain lysosomes (pH ~ 4.5–5.0) in live cells.

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A Novel Fluorescent Probe for Selective Detection of Hydrazine and Its Application in Imaging

Biosensors ◽

10.3390/bios11050130 ◽

2021 ◽

Vol 11 (5) ◽

pp. 130

Author(s):

Ruo-Jun Man ◽

Meng-Ke Wu ◽

Bing Yang ◽

Yu-Shun Yang

Keyword(s):

Fluorescent Probe ◽

Water Samples ◽

High Selectivity ◽

High Sensitivity ◽

Living Cells ◽

Environmental Toxicology ◽

Future Research ◽

Selective Detection ◽

Anti Cancer ◽

First Time

In this work, a novel fluorescent probe with first-time-selected thiazepine backbone, TZPzine-1, was developed for selective detection of hydrazine in water samples and living cells. Chosen from our recent anti-cancer agents, TZPzine-1 inferred structurally based advantages of the optical adjustability and the hydrazine-trapping approach. It also showed applicable properties including high sensitivity (LOD = 50 nM), wide linear range (0–15 equiv.), high selectivity (especially from competing species), rapid response (within 20 min), and practical steadiness in various pH (6.0–11.0) and temperature (15–50 °C) conditions. To satisfy the interdisciplinary requirements in environmental toxicology, TZPzine-1 was successfully applied in water samples and living cells. We hope that the information in this work, as well as the concept of monitoring the nitrogen cycle, may be referable for future research on systematic management.

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A Phenothiazine-HPQ Based Fluorescent Probe with a Large Stokes Shift for Sensing Biothiols in Living Systems

Molecules ◽

10.3390/molecules26082337 ◽

2021 ◽

Vol 26 (8) ◽

pp. 2337

Author(s):

Yan Zheng ◽

Peng Hou ◽

Yu Li ◽

Jingwen Sun ◽

Hongxia Cui ◽

...

Keyword(s):

Fluorescent Probe ◽

Fluorescence Enhancement ◽

Stokes Shift ◽

Redox Properties ◽

Living Systems ◽

Selective Detection ◽

Large Stokes Shift ◽

Low Cytotoxicity ◽

Mcf 7

Due to the redox properties closely related to numerous physiological and pathological processes, biothiols, including cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), have received considerable attention in biological science. On account of the important physiological roles of these biothiols, it is of profound significance to develop sensitive and selective detection of biothiols to understand their biological profiles. In this work, we reported an efficient fluorescent probe, PHPQ-SH, for detecting biothiols in vitro and vivo, based on the phenothiazine-HPQ skeleton, with DNBS (2,4-dinitrobenzenesulfonate) as the response unit. Probe PHPQ-SH exhibited brilliant sensing performances toward thiols, including a large Stokes shift (138 nm), excellent sensitivity (for GSH, LOD = 18.3 nM), remarkable fluorescence enhancement (163-fold), low cytotoxicity, rapid response (8 min), and extraordinary selectivity. Finally, the probe PHPQ-SH illustrated herein was capable of responding and visualizing biothiols in MCF-7 cells and zebrafish.

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A Flavone Fluorescent Probe for Cysteine Detection

Asian Journal of Chemistry ◽

10.14233/ajchem.2019.22286 ◽

2019 ◽

Vol 31 (12) ◽

pp. 2909-2914

Author(s):

Saleh N. Al-Busafi ◽

Salma M. Al-Kindi ◽

Fakhr Eldin O. Suliman ◽

Aliya A. Al-Kalbani

Keyword(s):

Amino Acids ◽

Fluorescent Probe ◽

1H Nmr ◽

Michael Addition ◽

Addition Reaction ◽

Fluorescence Emission ◽

Selective Detection ◽

Michael Addition Reaction ◽

Uv Visible ◽

The Michael Addition

A new blue-emitting fluorescent probe 1 based on flavone structure was prepared for the selective detection of cysteine. The probe was prepared through three synthetic steps from commercially available starting materials. Selective detection of cysteine by probe 1 in the presence of other non-thiol amino acids was established by UV-visible and fluorescent experiments. A remarkable fluorescence emission was observed at 469 nm when cysteine was mixed with probe 1. The Michael addition reaction of cysteine to probe-1 was confirmed by 1H NMR technique.

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Synthesis of a new highly sensitive near-infrared fluorescent iridium(iii) probe and its application for the highly selective detection of glutathione

RSC Advances ◽

10.1039/c5ra14847b ◽

2015 ◽

Vol 5 (103) ◽

pp. 85095-85104 ◽

Cited By ~ 6

Author(s):

Hailang Chen ◽

Xiaofeng Bao ◽

Feng Li ◽

Baojing Zhou ◽

Renlong Ye ◽

...

Keyword(s):

Fluorescent Probe ◽

Near Infrared ◽

High Selectivity ◽

Selective Detection ◽

Near Ir ◽

Highly Sensitive

A new near-IR fluorescent probe (probe 1) based on the IR 780 skeleton exhibits high selectivity and sensitivity towards Ir(iii) in an EtOH/H2O solution. The probe 1–Ir(iii) complex was also used for the highly selective detection of glutathione.

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