Ultra-sensitive high-selectivity hypochlorous acid colorimetric fluorescence probe

A compound and straight-chain technology, applied in 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 Effect

Inactive Publication Date: 2017-08-29
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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  • Ultra-sensitive high-selectivity hypochlorous acid colorimetric fluorescence probe
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  • Ultra-sensitive high-selectivity hypochlorous acid colorimetric fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038]

[0039] (Scheme 1) Dissolve 1.6017g (10mmol) 1,6-dihydroxynaphthalene and 3.1335g (10mmol) 4-diethylamino ketoacid in (10mL) trifluoroacetic acid (TFA), then heat to reflux for 24h, and then Add 15 mL of ethyl acetate and heat to reflux for 15 min, cool to room temperature, recrystallize and filter with suction to obtain 3.9420 g of pure product with a yield of 90%.

[0040] (Scheme 2) Dissolve 1.6017g (10mmol) 1,6-dihydroxynaphthalene and 3.4469g (11 mmol) 4-diethylamino ketoacid in (10mL) trifluoroacetic acid (TFA), then heat to reflux for 24h, and then Add 15 mL of ethyl acetate and heat to reflux for 15 min, cool to room temperature, recrystallize and filter with suction to obtain 3.9858 g of pure product with a yield of 91%.

[0041] (Scheme 3) Dissolve 1.6017g (10mmol) 1,6-dihydroxynaphthalene and 3.7602g (12 mmol) 4-diethylamino ketoacid in (10mL) trifluoroacetic acid (TFA), then heat to reflux for 24h, and then Add 15 mL of ethyl acetate and heat to reflux fo...

Embodiment 2

[0046] The inventor of the present invention has carried out following test: (a) under the condition of PBS pH=5.0 hypochlorous acid of different concentrations is to the influence of probe (20 μ M) solution color; (b) under the condition of PBS pH=7.4 hypochlorous of different concentrations The effect of acid on the color of the probe (20μM) solution; (c) is the effect of HOCl (5μM) on the fluorescence spectrum of the probe (5μM) under the condition of PBS pH=5.0; (d) is the effect of HOCl under the condition of PBS pH=7.4 (5 μM) on the fluorescence spectrum of the probe (5 μM). The above measurements were carried out in a pure aqueous solution of 10 mM PBS, the probe used was the probe prepared in Example 1, and all spectral tests were measured at 25° C. after the addition of HOCl for 1 min. See Figure 1 for the results.

[0047] From figure 1 (a) as can be seen, the hypochlorous acid that concentration increases gradually under the condition of PBS pH=5.0 can make probe ...

Embodiment 3

[0049] Test results of probe (5 μM) response time to HOCl (5 μM). The above-mentioned determination is carried out in 10mM PBS, the aqueous solution of pH=5.0, and the probe used is the probe prepared in embodiment 1, and all spectral tests are all measured under 25 ℃. See results figure 2 .

[0050] From figure 2 It can be seen that after adding isochlorous acid, the fluorescence intensity drops suddenly, and the response can be completed within 5s.

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Abstract

The invention relates to an ultra-sensitive high-selectivity hypochlorous acid colorimetric fluorescence probe. Concretely, the probe provided by the invention is a class of rhodamine compounds, and can be used as the hypochlorous acid colorimetric fluorescence probe for detecting hypochlorous acid. The class ofSuch probe can realize at least one of the following technical effects: the hypochlorous acid can be recognized in an ultra-sensitive high-selectivity way and is detected accurately; the hypochlorous acid can be quickly responded; the hypochlorous acid can be detected instantly; the probe is stable in property, can be stored and used for a long time, and is beneficial for detecting (in vivo/in vitro) hypochlorous acid in an actual sample.

Description

technical field [0001] The present invention relates to a rhodamine compound that is induced by chloride ions to form a ring as a colorimetric fluorescent probe for hypochlorous acid, which can perform rapid, ultra-sensitive and highly selective detection of endogenous hypochlorous acid in cells, or can be used as a hypochlorous acid colorimetric fluorescent probe. Determination of 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 due to excessive hypochlorous acid concentration in swimming pool water still occur frequently. Excessive hypochlorous acid pro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/78C09K11/06G01N21/64
CPCC07D311/78C09K11/06C09K2211/1088G01N21/643G01N2021/6432
Inventor 王雅伟吴柳张萌赵子扬李雪妍柳彩云朱宝存
Owner UNIV OF JINAN
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