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Preparation and application of sulfo-carbamate hypochlorous acid fluorescent probe

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

Inactive Publication Date: 2017-10-20
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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 sulfo-carbamate hypochlorous acid fluorescent probe
  • Preparation and application of sulfo-carbamate hypochlorous acid fluorescent probe
  • Preparation and application of sulfo-carbamate hypochlorous acid fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] (Scheme 1) Tricyanotrimethylfuran (398 mg, 2 mmol) and phenyl p-formylthiocarbamate (419 mg, 2 mmol) were dissolved in 20 mL of absolute ethanol, and then diisopropylethyl Amine (646mg, 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 gel column (dichloromethane: petroleum ether = 2:1 as the eluent) to obtain 648 mg of a yellow solid with a yield of 83%.

[0035] (Scheme 2) Tricyanotrimethylfuran (398 mg, 2 mmol) and phenyl p-formylthiocarbamate (460 mg, 2.2 mmol) were dissolved in 20 mL of absolute ethanol, and then diisopropylethyl amine (646mg, 3mmol), 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 s...

Embodiment 2

[0039] 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 1 .

[0040] figure 1 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 603nm gradually increases with the increase of hypochlorous acid concentration. Moreover, a good linear relationship is maintained be...

Embodiment 3

[0042]Test results of probe (5 μM) response time to hypochlorous acid (5 μM). The above determinations were carried out in 10mM 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 2 .

[0043] from figure 2 It can be seen that after adding an equal concentration of hypochlorous acid, the fluorescence intensity rises suddenly, and the response can be completed within 1 min.

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PUM

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Abstract

The invention relates to a preparation and application of a sulfo-carbamate hypochlorous acid fluorescent probe. Specifically, the probe of the invention is a sulfo-carbamate compound which can be used as a hypochlorous acid fluorescent probe for detecting hypochlorous acid. The probe can realize at least one of the following technical effects: the hypochlorous acid can be sensitively and high selectively identified and can be accurately detected; rapid response to the hypochlorous acid can be realized; instant detection of the hypochlorous acid can be realized; the properties are stable, and the probe can be stored and used for a long time; and the hypochlorous acid (in vivo / vitro) in a real sample can be detected.

Description

technical field [0001] The invention relates to a thiocarbamate compound as a hypochlorous acid 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 concentration of hypochlorous aci...

Claims

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Application Information

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IPC IPC(8): C07D307/54C09K11/06G01N21/64
CPCC07D307/54C09K11/06C09K2211/1007C09K2211/1088G01N21/643
Inventor 闫语朱宝存
Owner 闫语
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