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Synthesis of multi-signal fluorescent probe and application of multi-signal fluorescent probe in simultaneously distinguishing Cys, SO2, GSH and Hcy

A technology of fluorescent probes and fluorescent molecular probes, applied in the field of analytical chemistry, can solve the problem that thiol fluorescent probes cannot be distinguished and detected by four channels at the same time

Active Publication Date: 2021-10-19
HUNAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, multi-signal fluorescent probes have attracted extensive attention because they can simultaneously monitor and visualize two or more analytes in living cells, but the reported thiol fluorescent probes have not been able to realize the simultaneous differential detection of Cys using four channels. , SO 2 , GSH and Hcy, four sulfur-containing compounds, develop while distinguishing Cys, SO 2 , GSH and Hcy multi-signal fluorescent probes have great application value in the fields of analysis and detection, environmental science and biochemistry

Method used

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  • Synthesis of multi-signal fluorescent probe and application of multi-signal fluorescent probe in simultaneously distinguishing Cys, SO2, GSH and Hcy
  • Synthesis of multi-signal fluorescent probe and application of multi-signal fluorescent probe in simultaneously distinguishing Cys, SO2, GSH and Hcy
  • Synthesis of multi-signal fluorescent probe and application of multi-signal fluorescent probe in simultaneously distinguishing Cys, SO2, GSH and Hcy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1. Synthesis of 4-hydroxy-7-(pyrrolidin-1-yl)-2H-chromen-2-one

[0028] a. Diphenylmalonate (6.28 g, 24.51 mmol) and 3-(pyrrolidin-1-yl)phenol (2 g, 12.25 mmol) were added to anhydrous toluene (20 mL), and the reaction mixture was heated to 110 ℃ for 8 hours,

[0029] b. After the reaction is completed, filter, wash the filter cake 3 times with n-hexane, and dry in vacuo to obtain light yellow solid 4-hydroxy-7-(pyrrolidin-1-yl)-2H-chromen-2-one (2.0 g, 68% yield).

Embodiment 2

[0030] Example 2. Synthesis of 4-chloro-2-oxo-7-(pyrrolidin-1-yl)-2H-methylene-3-carbaldehyde

[0031] . Under nitrogen protection, slowly add 1.8 mL of dry redistilled N,N-dimethylformamide (DMF) to an equal volume of phosphorus oxychloride (POCl 3 ), stirred at 20-50°C for 30 minutes to obtain a red solution,

[0032] . 4-Hydroxy-7-(pyrrolidin-1-yl)-2H-chromen-2-one (1.0 g, 4.32 mmol) was dissolved in 5 mL N,N-dimethylformamide and added dropwise to step In the mixed solution, the mixture continued to stir and react at 60°C under nitrogen protection for 12 hours,

[0033] . After the reaction is complete, the step Slowly pour the reaction solution in 500 mL of ice water, adjust the pH to 6 with 20% NaOH solution, a large amount of precipitation occurs, filter, wash the filter cake with an appropriate amount of deionized water for 3 times, and dry the obtained solid in vacuum to obtain 4-chloro -2-Oxo-7-(pyrrolidin-1-yl)-2H-methylene-3-carbaldehyde

[0034] 0.74...

Embodiment 3

[0035] Example 3. Synthesis of 4-(butylthio)-2-oxo-7-(pyrrolidin-1-yl)-2H-methylene-3-carbaldehyde

[0036] . Add 0.20 g (720.19 mmol) of 4-chloro-2-oxo-7-(pyrrolidin-1-yl)-2H-methylene-3-carbaldehyde and 64.95 mg (720.19 mmol) of n-butanethiol to 20 mL In anhydrous dichloromethane, add 70 μL triethylamine dropwise, and stir the reaction at room temperature.

[0037] . After the reaction is complete, the step 4-(butylthio)-2-oxo-7-(pyrrolidin-1-yl)-2H-methylene-3-carbaldehyde was obtained by column chromatography of the reaction solution.

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Abstract

The invention discloses a multi-signal fluorescent molecular probe for simultaneously distinguishing and detecting cysteine (Cys), sulfur dioxide (SO2), glutathione (GSH) and homocysteine (Hcy) through different excitation and fluorescence emission signals. The chemical structural formula of the multi-signal molecular probe is shown in the specification. The multi-signal fluorescent probe can generate different fluorescent substances by different chemical reactions between the probe and Cys, NaHSO3, GSH and Hcy under the same detection condition, thereby achieving the purpose of simultaneously distinguishing and detecting Cys, SO2, GSH and Hcy. After the probe reacts with Cys, blue light of 464 nm is emitted under the excitation wavelength of 376 nm; after the probe reacts with NaHSO3, green light of 520 nm is emitted under the excitation wavelength of 425 nm; after the probe reacts with GSH, yellow-green light of 536 nm is emitted under the excitation wavelength of 450 nm; and after the probe reacts with Hcy, orange light of 564 nm is emitted under the excitation wavelength of 490 nm. The multi-signal fluorescent molecular probe can be used for simultaneous quantification in an in-vitro environment and simultaneous fluorescence imaging of Hcy, Cys, SO2 and GSH in cells.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to the synthesis of a multi-signal fluorescent probe, and the simultaneous quantitative detection of Cys and SO by the probe in the environment. 2 , GSH and Hcy, and simultaneously differentiate and image Cys and SO in cells 2 , GSH and Hcy applications. Background technique [0002] Bioactive molecules such as reactive sulfur, reactive nitrogen and reactive oxygen species play an extremely important role in maintaining the dynamic balance of redox in cells. Among them, as the reactive sulfur species (Reactive Sulfur Species: RSS) with the highest content in the active molecules in cells, it mainly includes biothiols (cysteine ​​(Cys), homocysteine ​​(Hcy), glutathione ( GSH), sulfur dioxide (SO 2 ), hydrogen sulfide (H 2 S) and active molecules such as N-acetylcysteine ​​(NAC) ( Anal. Chem. 2018, 90 , 533-555.). In mammals, Hcy can be synthesized fro...

Claims

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Application Information

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IPC IPC(8): C07D417/06C09K11/06G01N21/64
CPCC07D417/06C09K11/06G01N21/6428C09K2211/1029C09K2211/1037C09K2211/1088G01N2021/6439Y02P20/55
Inventor 尹鹏贺梦雪尹国兴甘亚兵李海涛
Owner HUNAN NORMAL UNIVERSITY