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Mitochondria target hydrogen peroxide molecular fluorescent probe and preparation method and application thereof

A technology of hydrogen peroxide and fluorescent probes, which is applied in the field of analytical chemistry, can solve the problems of inability to detect hydrogen peroxide, lack of hydrogen peroxide probes, and lack of targeting in detection, and achieve strong anti-interference ability of other molecules, The processing process is simple and the effect of high overlap rate

Inactive Publication Date: 2017-01-04
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, currently for H 2 o 2 The detection lacks targeting and cannot detect hydrogen peroxide in a specific organelle in the cell, especially the lack of hydrogen peroxide probes targeting the mitochondria in the cell, thus lacking the ability to study the excess of mitochondria in the process of cell disease. Detection tool for changes in hydrogen oxide concentration

Method used

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  • Mitochondria target hydrogen peroxide molecular fluorescent probe and preparation method and application thereof
  • Mitochondria target hydrogen peroxide molecular fluorescent probe and preparation method and application thereof
  • Mitochondria target hydrogen peroxide molecular fluorescent probe and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of compound 1:

[0031]

[0032] 4-Bromodiethylaminoaniline (1.0g, 2.4mmol, 1eq), palladium acetate (50mg, 0.2mmol, 0.1eq), tris(o-methylphenyl)phosphine (150mg, 0.5mmol, 0.3eq), Soluble in (volume ratio Et 3 N:DMF=5:3) in 30mL solution under nitrogen protection, then inject 4-vinylpyridine (1.0g, 9.6mmol, 4eq) into the above solution with a syringe. Heated at 120°C and reacted for 14 hours. Use a TCL plate to detect the reaction. After the reaction is complete, extract it with dichloromethane for 2-3 times, wash with saturated brine for 2-3 times, dry over anhydrous sodium sulfate, spin the solvent under reduced pressure to obtain a crude product, and separate it with a silica gel column to obtain For compound 1, the silica gel particle size is 200-300 mesh, and the eluent ratio is methanol / dichloromethane=1:10. The yield of compound 1 was 75%.

[0033] Compound Mito-H 2 o 2 Synthesis:

[0034]

[0035] Dissolve compound 1 (100mg, 0.396mmol, 1eq)...

Embodiment 2

[0037] Compound Mito-H 2 o 2 Changes of Fluorescence Spectrum of Hydrogen Peroxide Fluorescent Probe with Increase of Hydrogen Peroxide Equivalent

[0038] Get the Mito-H prepared in Example 1 2 o 2 The hydrogen peroxide fluorescent probe was dissolved in N,N-dimethylformamide (DMF) to make a 1 mmol / L stock solution. Take 30 μL from the stock solution and add it to a 5mL centrifuge tube, add hydrogen peroxide standard solutions of different equivalents (0-10eq), use PBS buffer solution (0.1mol / L, pH=8.3) and DMF volume ratio is 2: The solution of 1 was diluted to 3mL, and its fluorescence properties were measured with 410nm excitation light. Fluorescence spectra such as figure 2 shown. Depend on figure 2 It can be seen that the fluorescence gradually increases with the increase of hydrogen peroxide equivalent.

Embodiment 3

[0040] Compound Mito-H 2 o 2 Selectivity of Hydrogen Peroxide Fluorescent Probes to Different Molecules or Ions

[0041] Take 30 μL from the fluorescent probe stock solution in Example 2 and add it to a 5mL centrifuge tube, add equimolar amounts of competing molecular standard solutions, one of which is added with equimolar amounts of hydrogen peroxide standard solution, and use 410nm as the standard solution after 1h. Excitation light detects the change of fluorescence emission spectrum of the solution, the results are shown in image 3 and Figure 4 . Depend on image 3 and Figure 4 It can be found that other metal ions on the compound Mito-H 2 o 2 The fluorescence has almost no effect, and the addition of hydrogen peroxide solution makes the compound Mito-H 2 o 2 fluorescence was significantly enhanced.

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Abstract

The invention discloses a mitochondria target hydrogen peroxide molecular fluorescent probe and a preparation method and application thereof and belongs to the technical field of analytical chemistry. A molecular structural formula of the probe is shown as the formula I and is short as Mito-H2O2. The preparation method of the probe molecule is simple, achieves quick detection on hydrogen peroxide molecules, is good in selectivity and strong in antijamming capability, can be used for detecting hydrogen peroxide molecules in mitochondria of cells, has the characteristics of being quick, simple and flexible and has wide application prospect in the biological molecular detection field.

Description

technical field [0001] The invention relates to a mitochondria-targeted hydrogen peroxide molecular fluorescence probe, a preparation method and application thereof, and belongs to the technical field of analytical chemistry. Background technique [0002] Reactive oxygen species (ROS) is a general term for some substances containing oxygen atoms that play a very important role in many physiological and pathological processes in organisms, including free radicals (hydroxyl radicals and superoxide anion radicals, etc.) and non-free radicals (peroxidation hydrogen and hypochlorous acid, etc.). Among various reactive oxygen species (ROS), hydrogen peroxide is the most important one in living systems, and is the product of most oxidase processes and participates in many biological regulation processes. At normal physiological concentrations, H 2 o 2 It is beneficial to the normal physiological process of organisms, they are involved in the reversible oxidation of intracellular...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F5/04G01N21/64
CPCC07F5/04C09K11/06G01N21/6428
Inventor 林伟英任明光周凯邓贝贝
Owner UNIV OF JINAN
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