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Fluorescent probe for differentially detecting GSH and H2Sn (n is more than) through single-wavelength excitation

A fluorescent probe, single-wavelength technology, applied in the field of chemical analysis and detection, can solve the problem of short emission wavelength of fluorescent probes, and achieve the effect of wide application range and good cell membrane penetration

Active Publication Date: 2020-09-08
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In 2017, Chen et al. (Analytical Chemistry, 2017, 89(23), 12984-12991) reported the differential detection of GSH and H 2 S n (n>1) fluorescent probe, but the fluorescent probe has a shorter emission wavelength, in the blue and green light regions; in addition, dual-wavelength excitation is required in the application process
Currently, the development of single-wavelength excitation with long-wavelength emission for the differential detection of GSH and H 2 S n (n>1) fluorescent probes are still a challenge

Method used

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  • Fluorescent probe for differentially detecting GSH and H2Sn (n is more than) through single-wavelength excitation
  • Fluorescent probe for differentially detecting GSH and H2Sn (n is more than) through single-wavelength excitation
  • Fluorescent probe for differentially detecting GSH and H2Sn (n is more than) through single-wavelength excitation

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Experimental program
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Effect test

Embodiment 1

[0039] Embodiment 1: the synthesis of compound 2

[0040] Resorcinol (7.707 g, 70.0 mmol) and compound 1 (0.979 g, 3.5 mmol) were dissolved in 10.0 mL of acetonitrile. The mixture was stirred at 0°C for 5 minutes. Sodium chlorite (1.112 g, 12.3 mmol) and sodium dihydrogen phosphate (1.896 g, 15.8 mmol; dissolved in 1.5 mL of water) were added to the above mixture. After stirring and reacting at 0°C for 30 minutes, it was poured into 50 mL of ice water. The mixture was acidified with 1mol / L hydrochloric acid solution to form a large amount of yellow precipitate. After suction filtration and washing, 0.751 g of a yellow-brown solid was compound 2, and the yield was 76.2%.

Embodiment 2

[0041] Embodiment 2: the synthesis of compound 3

[0042] Diphenyldiselenide (0.218 g, 0.7 mmol) and sodium borohydride (0.034 g, 0.9 mmol) were dissolved in 2.5 mL of absolute ethanol. Under the protection of nitrogen, the mixture was stirred and reacted at room temperature for 10 minutes to obtain compound 3 as a colorless transparent solution. The product of this step can be directly used in the next step of synthesis without further purification.

Embodiment 3

[0043] Embodiment 3: the synthesis of compound 4

[0044] Compound 2 (0.180 g, 0.6 mmol) and compound 3 (0.110 g, 0.7 mmol) were dissolved in 5.0 mL of anhydrous N,N-dimethylformamide. And triethylamine (240.0 μL, 1.8 mmol) was added as an acid-binding agent. The reaction was stirred at room temperature for 20 minutes, then the mixture was poured into 50 mL of water. and extracted with dichloromethane, and the organic layers were combined. The organic solvent was removed under reduced pressure to obtain 0.243 g of orange solid as compound 4 with a yield of 98.0%.

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Abstract

The invention discloses a fluorescent probe for distinguishing and detecting GSH and H2Sn (n is more than 1) by single excitation, and belongs to the technical field of chemical analysis and detection, wherein the molecular structural formula is defined in the specification. According to the invention, the probe emits green fluorescence after reacting with GSH, and emits red fluorescence after reacting with H2Sn; the probe can realize simultaneous distinguishing detection of GSH and H2Sn (n is more than 1) under single-wavelength excitation, and has the characteristics of good selectivity, high sensitivity, wider pH working range and the like; and the probe can emit red fluorescence in the detection process, so that the excellent properties show that the fluorescent probe has important application value in the fields of environment, biology and the like.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a single-wavelength excitation and simultaneous differential detection of GSH and H 2 S n (n>1) fluorescent probe, and the probe in the detection of GSH and H 2 S n (n>1) applications. Background technique [0002] Reactive sulfur species are indispensable in living organisms and play important roles in physiological and pathological processes. Glutathione (GSH) and polyhydrogen sulfide (H 2 S n (n>1)) plays an important role in anti-oxidation, apoptosis and signal transduction. With the pair of GSH and H 2 S n In-depth research on biological functions, more and more studies have shown that these two types of active sulfur are related to each other in biological systems. For example, cells use GSH as a source of sulfur, which is enzymatically produced by cystathionine-γ-lyase (CSE) and cystathionine-β-synthase (CBS). High lev...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/18C09K11/06G01N21/64
CPCC07D311/18C09K11/06G01N21/6402G01N21/6428C09K2211/1088C09K2211/1007
Inventor 刘兴江肜一凡魏柳荷
Owner ZHENGZHOU UNIV
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