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A lysosome-targeted ratiometric hypochlorous acid fluorescent probe

A fluorescent probe, ratiometric technology, applied in the field of chemical analysis and detection, to achieve the effect of good selectivity, fast response speed, and strong anti-interference ability

Active Publication Date: 2022-03-11
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ratiometric fluorescent probes for hypochlorous acid with targeting ability and fast response are still a challenge, as probes with targeting ability can be used to elucidate the subcellular distribution of hypochlorous acid and explain the biological functions of hypochlorous acid.

Method used

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  • A lysosome-targeted ratiometric hypochlorous acid fluorescent probe
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  • A lysosome-targeted ratiometric hypochlorous acid fluorescent probe

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Experimental program
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Effect test

Embodiment 1

[0029] Embodiment 1: the synthesis of compound 2

[0030] Compound 1 (2.306g, 10.0mmol) and n-butyl bromide (2.765g, 20mmol) were dissolved in 25mL of anhydrous dimethyl sulfoxide, then sodium hydroxide (0.800g, 20.0mmol) and a catalytic amount of potassium iodide were added, 100 ℃, refluxed for 6h, after the reaction was completed, cooled to room temperature, extracted three times with dichloromethane, and evaporated the solvent under reduced pressure to obtain a crude product, which was separated and purified by column chromatography (petroleum ether / dichloromethane=2 / 1, v / v) The product 2 was obtained as a colorless oily liquid. Yield: 2.5935 g; Yield: 95.0%.

Embodiment 2

[0031] Embodiment 2: the synthesis of compound 3

[0032] Under argon protection, N,N-dimethylformamide (0.51mL, 7.2mmol) was slowly added to phosphorus oxychloride (0.6mL, 7.2mmol), stirred in an ice-water bath for 15min, intermediate 2 (1.6767g , 6mmol) was dissolved in anhydrous N,N-dimethylformamide, then added to the above solution, refluxed at 60°C for 4h, after the reaction was completed, the mixture was poured into 50mL ice water, and then washed with 10% sodium hydroxide solution Neutralized, extracted three times with dichloromethane, dried the organic phase with anhydrous sodium sulfate, and evaporated the solvent under reduced pressure to obtain a crude product, which was separated and purified by column chromatography to obtain product 3 as a yellow solid. Yield: 1.3146 g; Yield: 70.1%.

Embodiment 3

[0033] Embodiment 3: the synthesis of compound 4

[0034] Aluminum powder (0.2025 g, 3.6 mmol) was added into anhydrous acetonitrile (15 mL), and stirred at room temperature for 5 min. Iodine (0.0306 g, 2.55 mmol) was added in portions to the mixture, and stirred under nitrogen protection. Compound 3 (0.9530 g, 3.0 mmol) was dissolved in anhydrous acetonitrile (15 mL), and added dropwise to the mixture. The resulting suspension was refluxed for 6h. After cooling to room temperature, the mixture was extracted 3 times with 100 mL of ethyl acetate. The organic phase was dried with anhydrous sodium sulfate, and the solvent was evaporated to dryness under reduced pressure to obtain a crude product, which was separated and purified by column chromatography (petroleum ether / dichloromethane=1 / 1, v / v) to obtain product 4 as a yellow oily liquid. Yield: 0.7891 g; Yield: 87.3%.

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Abstract

The invention discloses a lysosome-targeted ratiometric hypochlorous acid fluorescent probe, which belongs to the technical field of chemical analysis and detection. Its molecular structure formula is as follows: in the detection process, the probe has good selectivity, high sensitivity, Strong interference ability and so on. At the same time, the probe has the ability to target lysosomes. These excellent properties indicate that the fluorescent probe has important application value in the fields of environment and biology.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, in particular to a lysosome-targeted ratiometric hypochlorous acid fluorescent probe and the application of the probe in detecting hypochlorous acid. Background technique [0002] Reactive oxygen species, including singlet oxygen, hydrogen peroxide, superoxide radicals, and hypochlorous acid, play an important role in the physiological and pathological processes of mammalian life systems. Among them, hypochlorous acid is the most important reactive oxygen species, and with the help of myeloperoxidase (MPO), hydrogen peroxide and hypochlorite can be synthesized in immune cells. Hypochlorous acid not only has a lethal effect on pathogens in cells, but also plays a very important role in the immune defense of microorganisms. However, excessive production of hypochlorous acid can cause many diseases such as cancer, lung damage, arthritis, arteriosclerosis, etc. Therefore, it...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/04C09K11/06G01N21/64
CPCC07D513/04C09K11/06G01N21/6402G01N21/6428G01N21/6458C09K2211/1033C09K2211/1037
Inventor 刘兴江刘姣姣魏柳荷
Owner ZHENGZHOU UNIV
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