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Synthesis and application of a fluorescent probe for detecting hydrogen peroxide

A technology of hydrogen peroxide and fluorescent probes, which is applied in the field of analytical chemistry, can solve the problems that the fluorescence enhancement factor is difficult to reach more than 500, the acid-base stability of the probe is poor, and the synthesis of the probe is complicated, so as to achieve high quantum yield and fluorescence enhancement. The effect of high multiples and cheap and easy-to-obtain raw materials

Active Publication Date: 2020-09-25
BEIJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthesis of most probes is complicated, the quantum yield is not high, and the fluorescence enhancement factor is almost difficult to reach more than 500, and some probes have poor acid-base stability.

Method used

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  • Synthesis and application of a fluorescent probe for detecting hydrogen peroxide
  • Synthesis and application of a fluorescent probe for detecting hydrogen peroxide
  • Synthesis and application of a fluorescent probe for detecting hydrogen peroxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The synthetic route of this fluorescent probe is as follows:

[0043]

[0044] Preparation of 4-nitrophenylglyoxylic acid

[0045]

[0046] SeO 2 (0.167g, 1.5mmol), p-nitroacetophenone (0.165g, 1mmol) in a 25mL round-bottomed flask, under nitrogen protection, add anhydrous pyridine 10mL, heat the oil bath to 110°C and stir to reflux, after 1 hour TLC thin-layer chromatographic analysis to detect the progress of the reaction, 4 hours after the completion of the reaction, cooled to room temperature, filtered with a Buchner funnel, and filtered to remove the SeO 2 The precipitated solution was washed with 50 mL of ethyl acetate to wash the residue; the combined filtrates were treated with 1 mmol / L hydrochloric acid (20 mL), the organic layer was separated into organic layer 1, and the aqueous layer was extracted three times with ethyl acetate (50 mL) to obtain aqueous layer 2 And organic layer 2; After organic layer 1 and organic layer 2 merge, extract three times ...

Embodiment 2

[0056] Embodiment 2: the application of fluorescent probe of the present invention

[0057] The details of the detection mechanism of the fluorescent probe of the present invention to hydrogen peroxide are as follows. After the amino group of the fluorescent mother nucleus reacts with 4-nitrophenylglyoxylic acid, the fluorescence of the resulting probe molecule is masked due to the action of the nitro group. Under the action of hydrogen peroxide, the amide bond formed by 4-nitrophenylglyoxylic acid is partially broken and left, the structure of the fluorescent mother nucleus is restored, and strong fluorescence is emitted. The response process is as follows:

[0058]

[0059] High performance liquid chromatography was used to verify the action mechanism of the fluorescent probe of the present invention on hydrogen peroxide. The retention time of the liquid chromatogram of the probe is 12.873 minutes; the retention time of the fluorescent mother nucleus is 8.489 minutes; th...

Embodiment 3

[0061] Take the probe molecule solution (10μM) in the phosphate buffer solution (pH=7.4) to prepare the solution to be tested, then add various ions and molecules (the above 27 kinds) respectively, and then measure it at 37°C for 10 minutes, the solution has almost no fluorescence. However, the fluorescence of the probe solution that only added hydrogen peroxide was greatly enhanced (about 1200 times), showing that the fluorescent probe can specifically recognize hydrogen peroxide. When adding hydrogen peroxide to the solution of other ions and molecules, and measuring after 10 minutes at 37°C, the fluorescence of the probe solution is still significantly enhanced, and the fluorescent probe of the present invention has a strong resistance to the detection of hydrogen peroxide. Interference ability. The molecular detection limit of the probe is as low as 46nM, which is suitable for trace detection. When the pH is between 5 and 9, the detection of hydrogen peroxide by the probe...

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Abstract

The invention relates to synthesis and application of a fluorescent probe for detecting hydrogen peroxide and belongs to the field of fluorescent probes. The chemical structure of the compound is as shown in the specification, and the compound has excellent fluorescence properties such as high quantum yield and good stability. The probe is extremely weak in fluorescence, but the fluorescence intensity is rapidly enhanced (by up to 1200 times) after hydrogen peroxide acts on the probe for 10 minutes, and the probe has high quantum yield. The probe has the detection limit as low as 46nM, has high sensitivity, is of excellent selectivity and anti-interference performance in the aspect of hydrogen peroxide recognition, can be used for detecting hydrogen peroxide in vitro and in living cells, and thus has broad application prospects in the field of chemical analysis and detection.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and relates to a preparation method and application of a rhodamine derivative fluorescent probe that specifically recognizes hydrogen peroxide. Background technique [0002] Active oxygen includes superoxide radicals (0 2 ), hydroperoxy radicals (H0 2 ), hydroxyl radical (H0 ), peroxyl radical (R0 2 ), singlet oxygen ( 1 0 2 ) and hypochlorous acid (HOCl), etc. Hydrogen peroxide is an important reactive oxygen species that plays important roles in the physiology, metabolism and pathology of living organisms and the environment. Excessive levels of hydrogen peroxide in cells can lead to DNA damage, mutation and genetic instability. It is also an indicator of aging, disease-related oxidative stress, and the like. [0003] In living systems, the production, accumulation and elimination of hydrogen peroxide have diverse physiological and pathological consequences. Therefore, the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/10C09K11/06G01N21/64
CPCC07D493/10C09K11/06C09K2211/1007C09K2211/1088G01N21/6428
Inventor 胡利明黄鑫范浩茹魏登帅曾程初
Owner BEIJING UNIV OF TECH
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