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High-sensitivity high-selectivity fluorescence probe capable of real-time responding hypochlorous acid and application of high-sensitivity high-selectivity fluorescence probe

A technology of hypochlorous acid and hypochlorite, which is used in fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve the problems of slow response speed, complex synthesis, poor selectivity, etc., and achieves good stability, simple synthesis, and water solubility. Good results

Inactive Publication Date: 2015-04-22
山东省章丘市第四中学
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, the currently reported fluorescent probes still have many defects, such as low sensitivity, poor selectivity, slow response, and complex synthesis, etc.

Method used

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  • High-sensitivity high-selectivity fluorescence probe capable of real-time responding hypochlorous acid and application of high-sensitivity high-selectivity fluorescence probe
  • High-sensitivity high-selectivity fluorescence probe capable of real-time responding hypochlorous acid and application of high-sensitivity high-selectivity fluorescence probe
  • High-sensitivity high-selectivity fluorescence probe capable of real-time responding hypochlorous acid and application of high-sensitivity high-selectivity fluorescence probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] (Scheme 1) 122mg (1.0mmol) salicylaldehyde, 125mg (1.0mmol) o-aminothiophenol are dissolved in the mixed solvent of 15mL n-butanol and toluene (volume ratio is 7:3), then in 120 ℃ Reaction at constant temperature for 10h. Then the reaction solution was rotary evaporated to remove n-butanol and toluene to obtain a crude product, which was separated by column chromatography using a dichloromethane system to obtain 144 mg of a white pure product with a yield of 63%.

[0038] (Scheme 2) 183mg (1.5mmol) salicylaldehyde, 125mg (1.0mmol) o-aminothiophenol are dissolved in the mixed solvent of 15mL n-butanol and toluene (volume ratio is 7:3), then in 120 ℃ Reaction at constant temperature for 10h. Then the reaction solution was rotary evaporated to remove n-butanol and toluene to obtain a crude product, which was separated by column chromatography using a dichloromethane system to obtain 172 mg of a white pure product with a yield of 75%.

[0039] (Scheme 3) 244mg...

Embodiment 2

[0044] The inventor of the present invention has carried out following test: (a) the influence of different concentration NaClO (0~1000 μ M) on probe (5 μ M) fluorescence spectrum; linear relationship between. The above determination was carried out in a mixed system of acetonitrile and water (5:5, v / v, 5mM PBS, pH=7.4), the probe used was the compound prepared in Example 1, and all spectral tests were carried out Measured at 25°C after 2 minutes of NaClO addition. See Figure 1 for the results.

[0045] It can be seen from Figure 1 that with the increase of the concentration of NaClO in the probe solution, the fluorescence spectrum gradually increases, and in the range of NaClO concentration of 0-600 μM, the concentration of NaClO and the fluorescence intensity have a linear relationship. Therefore, NaClO in biological samples and water can be quantitatively analyzed by means of the probe of the present invention.

Embodiment 3

[0047] Effect of different analytes (200 μM) on the fluorescence spectra of probes (5 μM). Analytes include: Hydrogen peroxide H 2 o 2 , tert-butanol peroxide TBHP, potassium superoxide KO 2 , Hydroxyl radical·OH, tert-butanol peroxide radical·TBHP, sodium peroxynitrite NaONOO, sodium hypochlorite NaClO. All tests were carried out in a mixed system of acetonitrile and water (5:5, v / v, 5mM PBS, pH=7.4), the probe used was the compound prepared in Example 1, and all spectroscopic tests were carried out Measured 2 minutes after analyte addition at 25°C. Specifically, pipette 50 μL of the probe stock solution (1 mM) into a 10 mL colorimetric tube, then add 5 mL of acetonitrile, then pipette 200 μL of the above analyte stock solution (10 mM) into the colorimetric tube, and then pipette 0.5 mL of PBS solution (pH=7.4, 100 mM), and finally dilute to 10 mL with ultrapure water. Shake well, let stand for 2 minutes, then measure. The result is as figure 2 shown.

[0048] from ...

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Abstract

The invention relates to a high-sensitivity high-selectivity fluorescence probe capable of real-time responding hypochlorous acid and application of the high-sensitivity high-selectivity fluorescence probe. The fluorescence probe is a kind of 2-benzothiazoline phenol compounds specifically and can be used as the fluorescence probe to be used for detection of hypochlorous acid / hypochlorite. By utilizing the fluorescence probe, at least one of the technical effects can be realized, for example, hypochlorous acid / hypochlorite can be identified with high sensitivity and high selectivity, response to hypochlorous acid / hypochlorite can be realized instantly, real-time detection to hypochlorous acid / hypochlorite can be realized, the fluorescence probe is stable in character and can be stored and used for long term, detection to hypochlorous acid / hypochlorite is easy under the condition of physiological level, and the fluorescence probe has strong antijamming capability.

Description

technical field [0001] The invention relates to 2-benzothiazoline phenolic compounds as hypochlorous acid fluorescent probes, which can be used for real-time, high-sensitivity and high-selectivity recognition of hypochlorous acid under physiological conditions, or can be used to determine hypochlorous acid in biological samples and water. Chloric acid / hypochlorite concentration. Background technique [0002] Hypochlorous acid (HClO) or hypochlorite (ClO - ) is an extremely important type of reactive oxygen species, which plays a key role in the resistance of pathogens in vivo to the disinfection of drinking water in our daily life. In organisms, when pathogens invade, myeloperoxidase (MPO) in phagosomes catalyzes hydrogen peroxide and chloride ions to produce hypochlorite to eliminate pathogens and maintain the normal operation of organisms. In addition, hypochlorite can also regulate chemical changes in various biomolecules such as proteins, DNA, and RNS. In our daily li...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/60C09K11/06G01N21/64
CPCC07D277/66C09K11/06C09K2211/1037G01N21/64
Inventor 徐祖钧李昌旺
Owner 山东省章丘市第四中学
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