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Synthesis and Application of a Bifunctional Fluorescent Probe Simultaneously Differentiating Hydroxyl Radicals and Hydrogen Peroxide

A fluorescent probe, hydrogen peroxide technology, applied in the field of analytical chemistry, can solve the problem that there is no report on the simultaneous detection of dual-function fluorescent probes, etc.

Active Publication Date: 2022-04-15
HUNAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, no bifunctional fluorescent probes have been reported for the simultaneous detection of hydroxyl radicals and hydrogen peroxide.
It shows that there are still great challenges in the dual-channel simultaneous detection of hydroxyl radicals and hydrogen peroxide

Method used

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  • Synthesis and Application of a Bifunctional Fluorescent Probe Simultaneously Differentiating Hydroxyl Radicals and Hydrogen Peroxide
  • Synthesis and Application of a Bifunctional Fluorescent Probe Simultaneously Differentiating Hydroxyl Radicals and Hydrogen Peroxide
  • Synthesis and Application of a Bifunctional Fluorescent Probe Simultaneously Differentiating Hydroxyl Radicals and Hydrogen Peroxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1. Synthesis of methyl 3-(8-methoxy-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinoxalin-5(1H)-yl)propionate

[0028] a. Add 30g (175.31mmol) 3-fluoro-4-nitroanisole and 37.5g (227.9mmol) L-proline methyl ester hydrochloride to 200mL anhydrous acetonitrile, then add 73mL (525.9mmol) Triethylamine was heated and refluxed for 6 hours, filtered to remove triethylamine hydrochloride, and the solution was spin-dried,

[0029] b. Dissolve the spin-dried solution in 300mL of methanol, slowly add 46.76g (874.13mmol) of ammonium chloride and 57.15g (874.13mmol) of zinc powder, stir overnight at room temperature, then filter to remove the zinc powder, spin to dry the solvent, and solid Add water, filter and dry to get green solid,

[0030] c. Dissolve the green solid in 400mL of anhydrous tetrahydrofuran, add 36.4g (962.17mmol) sodium borohydride and 122mL (962.17mmol) boron trifluoride ether, and react at 90°C for 12 hours. After the reaction is complete, slowly pour it into wat...

Embodiment 2

[0032] Example 2. Synthesis of 3-(7-formyl-8-hydroxyl-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinoxalin-5(1H)-yl)propionic acid methyl ester

[0033] I. Under the condition of nitrogen protection, slowly add 10 mL (61.99 mmol) of phosphorus oxychloride (POCl 3 ), stirred at 20-50°C for 30-60 minutes to obtain a yellow solution, and 10 g (34.44 mmol) of 3-(8-methoxy-2,3,3a,4-tetrahydropyrrolo[1,2 -a] quinoxalin-5(1H)-yl) methyl propionate was dissolved in 40mL N,N-dimethylformamide (DMF), added dropwise to the yellow mixed solution, and the mixture continued to be under nitrogen protection Stir and react at 60°C for 12 hours; after the reaction is complete, pour the reaction solution into an appropriate amount of ice water, adjust the pH to 5-6 with 20% NaOH solution, then extract with ethyl acetate, and spin the organic layer to obtain a yellow liquid product .

[0034] II. Add 621.8mg (23.05mmol) of aluminum and 5.85g (23.05mmol) of iodine into 15mL of anhydrous acetonitrile, re...

Embodiment 3

[0035] Example 3. Synthesis of methyl 3-(7-(2,2-dicyanovinyl)-8-((4-(4,4,5,5-tetramethyl-1,3,2-di Oxaborolan-2-yl)benzyl)oxy)-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinoxalin-5(1H)-yl)propionate

[0036] i. 200 mg of methyl 3-(7-formyl-8-hydroxy-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinoxalin-5(1H)-yl)propionate (658.15μmol) and 4-bromophenylboronic acid pinacol ester 390.30mg (1.30mmol) were added in 8mL acetonitrile, then potassium carbonate 136.16mg (985.70μmol) was added, refluxed overnight, after the reaction was completed, column chromatography purified to obtain a yellow solid 120.0 mg, yield 35.09%.

[0037] ii. Add 120 mg (230.58 μmol) of the yellow solid in step i and 18.3 mg (276.69 μmol) of malononitrile into 6 mL of ethanol, then add a drop of piperidine, react overnight at room temperature, and filter to obtain the bifunctional fluorescent probe 3 -(7-(2,2-dicyanovinyl)-8-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolin-2-yl )benzyl)oxy)-2,3,3a,4-tetrahydropyrrolo[1,2-a]qui...

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Abstract

The invention discloses a dual-functional fluorescent probe for simultaneously distinguishing hydroxyl radicals and hydrogen peroxide. hydrogen oxide. Utilizing the aromatic addition property of hydroxyl radicals, cyan fluorescence at 490nm is emitted at an excitation wavelength of 430nm after the reaction; phenylboronic acid pinacol ester is oxidized by hydrogen peroxide to selectively detect hydrogen peroxide, and it emits at an excitation wavelength of 470nm Red fluorescence at 600nm. The difference between the two emissions is 110nm, and the spectral overlap is small, and the hydroxyl radical and hydrogen peroxide can be selectively and simultaneously detected. The probe has the advantages of good selectivity, high fluorescence quantum yield, and large Stokes shift in detecting hydroxyl radicals and hydrogen peroxide, and has great application prospects in technical fields such as analytical chemistry, life science, and biomedicine.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to the synthesis and application of a dual-functional fluorescent probe for simultaneously distinguishing hydroxyl radicals and hydrogen peroxide. These probes use different mechanisms to rapidly and selectively detect hydroxyl radicals and hydrogen peroxide from various reactive oxygen species. The cyan fluorescence channel selectively detects hydroxyl radicals, and the red fluorescence selective channel detects hydrogen peroxide. It has the advantages of Tox shift, high fluorescence quantum yield, high detection sensitivity and visual detection. Background technique [0002] Reactive oxygen species (ROS) are natural byproducts of normal cellular metabolism and play crucial roles in cellular signaling and redox balance in vivo (Nature, 2006, 443, 787–795). such as O 2 ·- , H 2 o 2 , OH, HOCl, 1 o 2 and ONOO - A variety of reactive oxygen species suc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/025C09K11/06G01N21/6428G01N21/6458C09K2211/1044C09K2211/1096
Inventor 尹鹏甘亚兵尹国兴喻婷李海涛
Owner HUNAN NORMAL UNIVERSITY