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Ratio type small-molecular fluorescent probe responding to ONOO<->, and preparation method and application thereof

A fluorescent probe and molecular probe technology, applied in the field of fluorescent probe detection, can solve the problems of high error, difficult identification and detection, etc., and achieve the effects of sensitive response, low detection limit and superior selectivity

Inactive Publication Date: 2020-07-03
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the existing analytical methods have high errors and can only be used for qualitative detection. For small and micro doses of ONOO - Difficult to accurately identify and detect

Method used

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  • Ratio type small-molecular fluorescent probe responding to ONOO&lt;-&gt;, and preparation method and application thereof
  • Ratio type small-molecular fluorescent probe responding to ONOO&lt;-&gt;, and preparation method and application thereof
  • Ratio type small-molecular fluorescent probe responding to ONOO&lt;-&gt;, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] like figure 1 As shown, the ratiometric small molecule fluorescent probe that responds to ONOO- uses 9-(2-carboxyphenyl)-6-(diethylamino)-1,2,3,4-tetrahydroxanthene as the fluorescence Group, with activated C=C double bond as reactive group; with cyclohexanone and 2-[4-(diethylamino)-2-hydroxy-benzoyl]benzoic acid and N,N-two Methylcinnamaldehyde is the raw material, and the molecular probe is 3-[(4-isopropylphenylene)-propenylene]-7-(pentane-3-allylbenzene)-10-o-tolyl-1 ,2,3,4-tetrahydroxanthene, its chemical structure is:

[0071]

[0072] The above detection ONOO - The preparation method of the ratiometric small molecule fluorescent probe: comprises the following steps:

[0073] 1) Put 140mL of concentrated sulfuric acid into the container, then add 10g of cyclohexanone and 31.3g of 2-[4-(diethylamino)-2-hydroxy-benzoyl]benzoic acid, stir and heat at 85°C for 2h, and react After the solution is cooled to room temperature, pour it into ice water, stir evenly, t...

Embodiment 2

[0095] Establish the molecular probe F obtained in embodiment 1 533 to ONOO - The linear working curve of concentration titration, detection steps include:

[0096] (1) Prepare a PBS buffer solution with pH=7.40 and a concentration of 10mM, and prepare ONOO with a concentration of 1mM - H 2 O standard solution and probe F at a concentration of 1 mM 533 DMSO solution;

[0097] (2) Take 0μL, 2.5μL, 5μL, 7.5μL, 10μL, 12.5μL, 15μL, 17.5μL, 20μL and 22.5μL of ONOO at a concentration of 1mM - A total of 10 parts of the standard solution were added to each fluorescence cuvette, 100 μL of 10 mM PBS buffered saline solution was added, and 100 μL of 0.05 mM probe F 533 DMSO solution, and finally add physiological saline to make up to 1mL, and mix well;

[0098] (3) After reacting for 30 minutes, measure the fluorescence intensity by a fluorescence spectrophotometer, obtain the ratio of fluorescence intensity, and detect ONOO - The excitation wavelength of the fluorescence intensi...

Embodiment 3

[0106] Peroxynitrite is one of the indicators for evaluating water pollution. In this embodiment, the small molecule fluorescent probe F 533 Detection of ONOO in water samples - The content steps include:

[0107] (1) The water sample to be tested and F 533 Mix according to the volume ratio of 1:4, take 900mL of the resulting solution; (2) add 100μL of F with a concentration of 0.05mM to it 533 , the resulting solution is preserved at room temperature for 1min and its fluorescence intensity is detected; (3) according to the obtained solution of the probe molecule in Example 2, the pair of ONOO -Concentration, the linear equation of fluorescence intensity ratio, and the calculation of fluorescence intensity get the water sample containing ONOO - content. will be from Figure 8 The fluorescence intensity values ​​obtained in Image 6 (B) The established fluorescence linear equation, the obtained value is 1.9mM, which is ONOO in rainwater - The content is 10.5mM.

[0108]...

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Abstract

The invention aims to provide a ratio type small-molecular fluorescent probe responding to ONOO <->, and a preparation method and an application thereof, and belongs to the field of fluorescent probedetection. The prepared molecular probe can be applied to detection of ratio type probe molecules of a biological sample. By taking 9-(2-carboxyphenyl)-6-(diethylamino)-1,2,3,4-tetrahydroxanthene as afluorescent group and an activated C=C double bond as a reaction active group, the fluorescent probe F533 has the advantages of rapid labeling reaction, high selectivity to ONOO<->, extremely low detection limit and simple and convenient synthesis method. The influence of external conditions in biological sample imaging is small, and the result is accurate. The small-molecular fluorescent probe has far-reaching significance for further understanding the action mechanism of ONOO<-> in the body.

Description

technical field [0001] The invention belongs to the field of fluorescent probe detection, especially relates to response ONOO - The ratiometric small molecule fluorescent probe and its preparation method and application. Background technique [0002] The excessive production of reactive oxygen species (ROS for short) in the body is considered to be a key factor in many pathologies, ONOO - It is a very strong oxidant in the biological system, which can react with a series of molecular targets, including proteins, lipids and nucleic acids, which can destroy molecules, cause damage to the inner membrane structure of cells, and eventually lead to a series of diseases, such as diabetes, Alzheimer's Alzheimer's disease, cancer, arthritis, autoimmune diseases, etc., so a probe was invented to complete the ONOO - Instant detection is very important. [0003] So far, high performance liquid chromatography-mass spectrometry, electrochemical analysis, capillary electrophoresis analy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/82C09K11/06G01N21/64
CPCC07D311/82C09K11/06G01N21/6402C09K2211/1088
Inventor 尤进茂陆姣李赞谭江坤孙志伟常芮
Owner QUFU NORMAL UNIV