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Preparation and applications of phenylboronic acid type hypochloric acid colorimetric fluorescence probe

A hypochlorous acid and preparation technology, which is applied in the direction of fluorescence/phosphorescence, luminescent materials, and material analysis through optical means, can solve the problems of complex synthesis, poor selectivity, and low sensitivity, and achieve simple synthesis, good stability, and low cost. cheap effect

Inactive Publication Date: 2017-11-17
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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 applications of phenylboronic acid type hypochloric acid colorimetric fluorescence probe
  • Preparation and applications of phenylboronic acid type hypochloric acid colorimetric fluorescence probe
  • Preparation and applications of phenylboronic acid type hypochloric acid colorimetric fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] (Scheme 1) Dissolve benzothiazole-2-acetonitrile (348mg, 2mmol) and p-aldehyde phenylboronic acid (300mg, 2mmol) in 20mL absolute ethanol, then add diisopropylethylamine (646mg, 3 mmol), and the reaction solution was reacted at room temperature for 6 hours. After the reaction was completed, the solvent was removed by rotary evaporation to obtain a crude product, which was then separated and purified with a silica gel column (dichloromethane: petroleum ether = 2:1 as the eluent) to obtain 508 mg of a yellow solid with a yield of 83%.

[0037] (Scheme 2) Dissolve benzothiazole-2-acetonitrile (348 mg, 2 mmol) and p-aldehyde phenylboronic acid (330 mg, 2.2 mmol) in 20 mL of absolute ethanol, then add diisopropylethylamine (646 mg , 3mmol), the reaction solution was reacted at room temperature for 6 hours. After the reaction was completed, the solvent was removed by rotary evaporation to obtain a crude product, which was then separated and purified with a silica...

Embodiment 2

[0042] The inventor of the present invention has carried out following test: (a) under the condition of PBS pH=7.4 hypochlorous acid of different concentrations influences on the absorption spectrum of probe solution; (b) the linear relationship diagram of quantitative analysis of hypochlorous acid by absorption spectrometry; The above measurements were carried out in an aqueous solution of 10 mMPBS, the probe used was the probe prepared in Example 1, and all spectral tests were measured at 25° C. for 1 min after the addition of hypochlorous acid. See Figure 1 for the results.

[0043] As can be seen from Figure 1, before adding hypochlorous acid, the absorption peak of the probe is at 320nm; after adding hypochlorous acid, as the concentration of hypochlorous acid increases, the absorption peak at 320nm gradually disappears and appears at 446nm a new absorption peak. The absorption peak was red-shifted by 126nm, and there was a perfect isosbestic point at 357nm, and the reac...

Embodiment 3

[0045] Under the condition of PBS pH=7.4, the impact of different concentrations of hypochlorous acid on the fluorescence spectrum of the probe solution, the illustration is the linear relationship diagram of the quantitative analysis of hypochlorous acid by fluorescence spectroscopy; the above-mentioned determination is carried out in the aqueous solution of 10mM PBS, so The probe used was the probe prepared in Example 1, and all spectral tests were measured at 25° C. after the addition of hypochlorous acid for 1 min. See results figure 2 .

[0046] figure 2 is the graph of the change of the fluorescence spectrum of the probe with different concentrations of hypochlorous acid. It can be seen from the figure that the probe has almost no fluorescence before adding hypochlorous acid; after adding hypochlorous acid, the fluorescence intensity at 515nm gradually increases with the increase of hypochlorous acid concentration. Moreover, a good linear relationship is maintained ...

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Abstract

The invention relates to preparation and applications of a phenylboronic acid type hypochloric acid colorimetric fluorescence probe, and more specifically discloses a phenylboronic acid compound. The phenylboronic acid compound can be taken as a hypochloric acid colorimetric fluorescence probe used in hypochloric acid detection. The hypochloric acid colorimetric fluorescence probe is capable of achieving at least one of the following technical effects: high sensitivity selective identification of hypochloric acid and accurate detection; rapid response on hypochloric acid; and real-time detection of hypochloric acid. The phenylboronic acid type hypochloric acid colorimetric fluorescence probe is stable in properties, can be stored for a long term, and is beneficial for detection of hypochloric acid (in vivo / in vitro) in practical samples.

Description

technical field [0001] The invention relates to a phenylboronic acid compound used as a hypochlorous acid colorimetric fluorescent probe, which can detect hypochlorous acid quickly, sensitively and with high selectivity in an aqueous solution, or can measure the concentration of hypochlorous acid in an actual water sample. Background technique [0002] In humans, hypochlorous acid can be produced in a regulated manner by 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 concentrat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/025C09K11/06C09K2211/1007C09K2211/1037G01N21/6428
Inventor 闫语舒伟朱宝存
Owner 闫语
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