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Silicon-based rhodamine-nitrogen oxide fluorescent probe and preparation method and application thereof

A silicon-based rhodamine and nitric oxide technology, applied in the fields of chemistry and biology, can solve the problems of lack of lysosome-specific positioning function, low concentration, poor chemical stability, etc., achieve small damage, reduce interference, and penetrate powerful effect

Inactive Publication Date: 2015-12-16
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

People have carried out extensive and in-depth research on nitric oxide, but nitric oxide molecule has poor chemical stability, is active in vivo, and has a half-life of less than 5 seconds; in addition, as a lipophilic small molecule, nitric oxide is very permeable. Through the cell membrane, it can quickly migrate from the place of production to other tissue cells; under physiological conditions, the concentration of nitric oxide in cells is extremely low, and it is easily converted into its stable metabolite NO 3- and NO 2-
The above-mentioned fluorescent probes can specifically recognize NO, but they use fluorescein and rhodamine as the parent structure, o-phenylenediamine as the recognition group, and the excitation wavelength and emission wavelength are in the visible region, and they do not have Lysosome-specific localization function

Method used

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  • Silicon-based rhodamine-nitrogen oxide fluorescent probe and preparation method and application thereof
  • Silicon-based rhodamine-nitrogen oxide fluorescent probe and preparation method and application thereof
  • Silicon-based rhodamine-nitrogen oxide fluorescent probe and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0060] The synthesis of embodiment 1 probe SiRB-NO

[0061] In a 50ml reaction flask equipped with a magnetic stirrer, add raw materials SiRB727mg (1.5mmol), ClCH 2 CH 2 Cl (10ml) dissolved, argon protection, magnetic stirring, at room temperature, slowly add POCl 3 0.55ml, after the dropwise addition, heat to reflux, after 4 hours of reaction, stop heating, naturally cool to room temperature, evaporate the solvent under reduced pressure, add 10mL of acetonitrile to dissolve the remaining solid, and set aside. In another 50mL reaction flask, add 973mg (9.0mmol) of o-phenylenediamine, 5mL of acetonitrile, 5mL of triethylamine, magnetically stir, and under the protection of argon, slowly introduce the acetonitrile solution of the previously obtained solid into the reaction solution, React overnight at room temperature. The solvent was evaporated to dryness under reduced pressure, and the residue was washed with 30 mL CH 2 Cl 2 Dissolve, then add 30mL water, extract, separat...

Embodiment 2

[0062] The synthesis of embodiment 2 probe Lyso-SiRB-NO

[0063] 1. Synthesis of Br-SiRB-NO:

[0064] In a 50mL reaction flask equipped with a magnetic stirrer, add the raw material Br-SiRB450mg (0.8mmol), ClCH 2 CH 2 Cl (5mL) dissolved, argon protection, magnetic stirring, at room temperature, slowly add POCl 3 0.3mL, after the dropwise addition, heat to reflux, after 4 hours of reaction, stop heating, naturally cool to room temperature, evaporate the solvent under reduced pressure, add 5mL of acetonitrile to dissolve the remaining solid, and set aside. In another 50mL reaction flask, add 519mg (4.8mmol) of o-phenylenediamine, 4mL of acetonitrile, 4mL of triethylamine, magnetically stir, and under the protection of argon, slowly introduce the acetonitrile solution of the previously obtained solid into the reaction solution, React overnight at room temperature. The solvent was evaporated to dryness under reduced pressure, and the residue was washed with 30 mL CH 2 Cl 2 D...

Embodiment 3

[0067] Example 3: Determination of Fluorescence Changes of Probe SiRB-NO at Different pH

[0068] 1. Probe SiRB-NO high standard solution configuration

[0069] Accurately weigh a certain amount of probe SiRB-NO, and use acetonitrile solvent to prepare a high-standard solution with a concentration of 0.5mM.

[0070] 2. Measurement of the fluorescence change of the probe SiRB-NO itself at different pH

[0071] Pipette 20 μL of the probe master solution and add 2000 μL of phosphate buffer (0.1M, containing 20% ​​acetonitrile ), the fluorescence value was measured after 15 minutes, the excitation wavelength was 630nm, and the detection wavelength was 682nm. Fluorescent effect see attached Figure 5 .

[0072] 3. Determination of the effect of different pH on the recognition performance of SiRB-NO in nitric oxide

[0073] Pipette 20 μL of the probe mother solution into 2000 μL of phosphate buffer solution with different pH (2.0, 3.0, 4.0, 5.0, 6.0, 7.0, 7.4, 8.0, 9.0, 10.0, 1...

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Abstract

The invention relates to a silicon-based rhodamine-nitrogen oxide fluorescent probe. The structures of the probe are shown in the following figures (please see the figures in the specification), wherein the Lyso-SiRB-NO in the figure II has a lysosome positioning function. The probe has the advantages that excitation and emission wavelengths of the probe are located in a near infrared light area, and when the probe is applied to biological imaging, the interference of the fluorescent background of a living body itself can be reduced; the probe is high in penetrating power and little damages tissue or cells of the living body; the probe can specifically detect nitrogen oxide molecules in lysosome, and a reliable research tool is provided for research on the physiological effect of nitrogen oxide molecules.

Description

technical field [0001] The invention relates to the fields of chemistry and biotechnology, in particular to a silicon-based rhodamine nitric oxide fluorescent probe and its preparation method and application. Background technique [0002] Nitric oxide is a very important biological information molecule in organisms. Nitric oxide in the body is produced by the oxidation of L-arginine catalyzed by nitric oxide synthetase (NOS). Studies have shown that nitric oxide participates in many important physiological processes in the body, especially plays an important role in the cardiovascular system, and has the functions of relaxing blood vessels, preventing thrombosis, and resisting atherosclerosis. People have carried out extensive and in-depth research on nitric oxide, but nitric oxide molecule has poor chemical stability, is active in vivo, and has a half-life of less than 5 seconds; in addition, as a lipophilic small molecule, nitric oxide is very permeable. Through the cell...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08G01N21/64
Inventor 汪亭王保刚柴晓云吴秋业俞世冲张志强付奔
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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