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Preparation and application of ultra-sensitive high-selectivity hypochlorous acid fluorescence probe

A preparation and selected technology are applied in the field of fluorescein compounds as hypochlorous acid fluorescent probes, which can solve the problems of complex synthesis, poor selectivity and low sensitivity, and achieve the effects of simple synthesis, good stability and low cost

Inactive Publication Date: 2018-03-02
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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  • Preparation and application of ultra-sensitive high-selectivity hypochlorous acid fluorescence probe
  • Preparation and application of ultra-sensitive high-selectivity hypochlorous acid fluorescence probe
  • Preparation and application of ultra-sensitive high-selectivity hypochlorous acid fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] (Scheme 1) Dissolve 332.3mg (1mmol) fluorescein and 494.4mg (4mmol) dimethylaminothioformyl chloride in dichloromethane and add 460.8mg (4mmol) diisopropylethylamine for normal temperature (25°C) After stirring for 20 h, column chromatography was performed using a dichloromethane system to obtain 304 mg of a yellow solid with a yield of 60%.

[0037] (Scheme 2) Dissolve 332.3mg (1mmol) fluorescein and 741.6mg (6mmol) dimethylaminothioformyl chloride in dichloromethane and add 691.2mg (6mmol) diisopropylethylamine for normal temperature (25°C) Stir for 20 h, and use dichloromethane system for column chromatography to obtain 350 mg of yellow solid with a yield of 69%.

[0038] (Scheme 3) Dissolve 332.3mg (1mmol) fluorescein and 988.8mg (8mmol) dimethylaminothioformyl chloride in dichloromethane and add 921.6mg (8mmol) diisopropylethylamine for normal temperature (25°C) After stirring for 20 h, column chromatography was performed using a dichloromethane system...

Embodiment 2

[0043] The inventors of the present invention have carried out following test:

[0044] Test results of probe (5 μM) response time to HOCl (8 μM). The above determinations were carried out in 5mM PBS, 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 .

[0045] from figure 1 It can be seen that after adding 8 μM hypochlorous acid, the fluorescence intensity suddenly increases, and the response can be completed within 3s.

Embodiment 3

[0047] The effect of different concentrations of hypochlorous acid (0~8μM) on the fluorescence spectrum of the probe (5μM). The above measurements were carried out in an aqueous solution of 5 mM 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 and 3 .

[0048] from figure 2 and 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 from 0 to 40 nM, the concentration of hypochlorous acid and the fluorescence intensity show a good linear relationship, and The detection limit was as low as 0.65nM. 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 preparation and application of an ultra-sensitive high-selectivity hypochlorous acid fluorescence probe. Specifically, the probe is one category of fluorescein compound andcan be used as the hypochlorous acid fluorescence probe for detecting hypochlorous acid. The category of probes can realize at least one of the following technical effects: the hypochlorous acid can be identified in an ultra-sensitive high-selectivity way and can be accurately detected; the hypochlorous acid can be quickly responded; the hypochlorous acid can be detected immediately; properties are stable, and the ultra-sensitive high-selectivity hypochlorous acid fluorescence probe can be stored and used for a long time; the ultra-sensitive high-selectivity hypochlorous acid fluorescence probe is favorable for detecting (in vivo / in vitro) hypochlorous acid in a practical sample.

Description

technical field [0001] The invention relates to a fluorescein compound used as a fluorescent probe for hypochlorous acid, which can detect endogenous hypochlorous acid in cells quickly, ultrasensitively and with high selectivity, or can measure the concentration of hypochlorous acid in actual water samples. Background technique [0002] Hypochlorous acid is an extremely important reactive oxygen species, which is produced by the chemical reaction of hydrogen peroxide and chloride ions under the catalysis of myeloperoxidase (MPO), and is mainly distributed in the lysosomes of phagocytes. Plays an important role in the human immune system. In terms of hypochlorous acid in vitro, swimming pool poisoning incidents still occur frequently due to excessive hypochlorous acid concentration in swimming pool water. Excessive hypochlorous acid produced or accumulated in organisms can cause respiratory diseases, rheumatoid arthritis, neurological and cardiovascular and cerebrovascular d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10C09K11/06G01N21/64
CPCC07D493/10C09K11/06C09K2211/1088G01N21/6428G01N21/643
Inventor 吴柳张萌赵子扬袁瑞芳房钊彤王瑞康柳彩云朱宝存
Owner UNIV OF JINAN
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