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Fluorescent probe compound, preparation method and application of fluorescent probe compound as superoxide anion indicator

A technology of superoxide anion and fluorescent probe, which is applied in the preparation of organic compounds, preparation of amino hydroxyl compounds, chemical instruments and methods, etc., can solve problems such as death and cell damage, and achieve small damage to cells and living bodies and biocompatibility Good performance, cheap and easy-to-obtain raw materials

Pending Publication Date: 2022-05-10
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when the body's redox homeostasis is out of balance, O 2 ·- Abnormally high concentration will lead to cell damage and even death

Method used

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  • Fluorescent probe compound, preparation method and application of fluorescent probe compound as superoxide anion indicator
  • Fluorescent probe compound, preparation method and application of fluorescent probe compound as superoxide anion indicator
  • Fluorescent probe compound, preparation method and application of fluorescent probe compound as superoxide anion indicator

Examples

Experimental program
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Effect test

Embodiment 1

[0048] Example 1 Fluorescent Probe Cell membrane-O 2 ·- Preparation and structure elucidation

[0049] Fluorescent probe Cell membrane-O 2 ·- The preparation method comprises the steps:

[0050] (1) Dissolve the raw materials 3-bromopropyltrimethylammonium bromide (5mmol) and triethylamine (5.5mmol) in the reaction solvent 10mL N, N-dimethylformamide to activate the carboxyl group at 80°C for 15min;

[0051] (2) Add caffeic acid (5 mmol), and stir at 80° C. for 6 h;

[0052] (3) After the above reaction was completed, the solvent was removed by rotary evaporation under reduced pressure, and the heating temperature was 70°C. Use ethyl acetate:methanol=3:1 as developing solvent, carry out thin-layer chromatography chromatographic separation and purification, finally obtain light yellow fluorescent probe Cellmembrane-O 2 ·- (30%).

[0053] Mass Spectrometry Characterization:

[0054] HRMS(ESI)m / z:[M-H]calculated for C 15 h 22 NO 4 + , 280.1549found 280.1537. NMR char...

Embodiment 2

[0056] Example 2 O 2 ·- in vitro testing

[0057] Usually, the amphiphilic fluorescent probe Cell membrane-O 2 ·- Dissolve in physiological saline, PBS buffer or organic solvents such as methanol and dimethyl sulfoxide, and then add appropriate buffer and other organic reagents for testing. The probe Cell membrane-O was studied separately 2 ·- Photophysical properties and cytotoxicity in cells in a cell disruption solution simulating a physiological environment.

[0058] Probe Cell membrane-O 2 ·- with O 2 ·- UV absorption, fluorescence emission, reversible change, photostability and selectivity experiments of the reaction

[0059] Control group: Cell membrane-O 2 ·- (400μM), cell disruption solution, DMSO; experimental group: Cell membrane-O 2 ·- (400μM), cell disruption solution, O 2 ·- (20 μM). Add 0 and 20 μM O to the probe 2 ·- , measure its ultraviolet absorption spectrum, as the control group and the experimental group, its spectrum is shown in figu...

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Abstract

The invention relates to a fluorescent probe compound, a preparation method and application of the fluorescent probe compound as a superoxide anion indicator. The invention provides a fluorescent probe compound with the following structure. The compound can be specifically combined with superoxide anions and emit fluorescence, and can be used as a cell membrane superoxide anion indicator to be applied to the fields of early diagnosis of diseases and the like.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probe compounds, in particular to a fluorescent probe compound Cellmembrane-O 2 ·- , the preparation method of the fluorescent probe and its application as a superoxide anion indicator. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Intracellular redox balance plays an important role in maintaining the normal life activities of the body. Intracellular reactive oxygen species (ROS) such as superoxide anion radicals (O 2 ·- ), singlet oxygen ( 1 o 2 ), hydrogen peroxide (H 2 o 2 ), etc., play a key role in the regulation of various life activities. o 2 ·- is the first ROS molecule...

Claims

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Application Information

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IPC IPC(8): C07C219/10C07C213/00C09K11/06G01N21/64A61K49/00
CPCC07C219/10C07C213/00C09K11/06G01N21/6428A61K49/0021C09K2211/1007
Inventor 唐波李平张雯樊文杰
Owner SHANDONG NORMAL UNIV
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