Probe for ultra-sensitively and high-selectively detecting hypochlorous acid

A technology of sulfonic acid groups and compounds, which is applied in the field of probes for ultrasensitive and highly selective detection of hypochlorous acid, can solve the problems of complex synthesis, poor selectivity, and low sensitivity, and achieve simple synthesis, good stability, and low cost. Effect

Inactive Publication Date: 2018-08-17
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still some problems with the fluorescent probes reported so far, including low sensitivity, poor selectivity, and complex synthesis.

Method used

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  • Probe for ultra-sensitively and high-selectively detecting hypochlorous acid
  • Probe for ultra-sensitively and high-selectively detecting hypochlorous acid
  • Probe for ultra-sensitively and high-selectively detecting hypochlorous acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] (Scheme 1) Dissolve 324.28mg (2mmol) 7-hydroxycoumarin and 860.32mg (8mmol) dimethylaminothioformyl chloride in dichloromethane and add 1033.92mg (8mmol) DIPEA to stir at room temperature for 20h. The methane system was separated by column chromatography to obtain 305 mg of a yellow solid with a yield of 71.4%.

[0037] (Scheme 2) Dissolve 324.28mg (2mmol) 7-hydroxycoumarin and 1483.2mg (12mmol) dimethylaminothioformyl chloride in dichloromethane and add 1551.6mg (12mmol) DIPEA and stir at room temperature for 20h. The methane system was separated by column chromatography to obtain 320 mg of a yellow solid with a yield of 76.1%.

[0038] (Scheme 3) Dissolve 324.28mg (2mmol) 7-hydroxycoumarin and 1977.6mg (16mmol) dimethylaminothioformyl chloride in dichloromethane and add 2068.8mg (16mmol) DIPEA and stir at room temperature for 20h. The methane system was separated by column chromatography to obtain 350 mg of a yellow solid with a yield of 83.3%.

[0039] ...

Embodiment 2

[0043] Test results of probe (5 μM) response time to HClO (30 μM). The above measurements were carried out in 5mMPBS, pH 7.4 aqueous solution, the probe used was the probe prepared in Example 1, and all spectral tests were measured at 25°C. See results figure 1 .

[0044] from figure 1 It can be seen that after adding 30 μM hypochlorous acid, the fluorescence intensity suddenly increases, and the response can be completed within 5 seconds.

Embodiment 3

[0046] Effects of different concentrations of hypochlorous acid (0-30 μM) on the fluorescence spectrum of the probe (5 μM). The above measurements were carried out in an aqueous solution of 5mM PBS, pH 7.4, the probe used was the probe prepared in Example 1, and all spectral tests were measured at 25°C for 1 min. See results figure 2 with image 3 .

[0047] from image 3 It can be seen that with the increase of the concentration of hypochlorous acid in the probe solution, the fluorescence spectrum is gradually enhanced, and within the concentration range of hypochlorous acid of 0-175pM, the concentration of hypochlorous acid and the fluorescence intensity show a linear relationship, and the detected The limit is as low as 17pM. Therefore, the probe of the present invention can more accurately determine the content of hypochlorous acid in the sample to be tested.

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Abstract

The invention relates to a probe for ultra-sensitively and high-selectively detecting hypochlorous acid. Specifically, the probe provided by the invention is a coumarins compound, which can be used asa hypochlorous acid fluorescent probe for the detection of hypochlorous acid. The probe can achieve at least one of the following technical effects of ultra-sensitively and high-selectively identifying hypochlorous acid and performing accurate detection; rapidly responding to hypochlorous acid; realizing immediate detection on hypochlorous acid; being stable in property and being stored for use for a long time; being beneficial to detecting (in vivo/in vitro) hypochlorous acid in a practical sample.

Description

technical field [0001] The present invention relates to coumarin compounds as fluorescent probes for hypochlorous acid, which can perform rapid, ultra-sensitive and highly selective detection of endogenous hypochlorous acid in pure water systems, or can measure hypochlorous acid in actual water samples acid concentration. Background technique [0002] In humans, hypochlorous acid (HClO) can be produced in a regulated manner from the myeloperoxidase (MPO)-catalyzed reaction of hydrogen peroxide and chloride ions, which is important for innate host defense and for killing various pathogens. In vitro, swimming pool poisoning incidents due to high concentrations of hypochlorous acid in swimming pool water still occur frequently. Excessive production or accumulation of hypochlorous acid in organisms can cause a variety of diseases, including cardiovascular disease, atherosclerosis, osteoarthritis, rheumatoid arthritis and lung damage, and even cancer. Therefore, detecting the c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06C09K2211/1088G01N21/643
Inventor 柳彩云吴柳王雅伟赵子扬王作凯贾盼张萌朱宝存
Owner UNIV OF JINAN
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