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Targeted cell membrane surface GABA receptor fluorescent probe and preparation method and application thereof

A fluorescent probe, cell membrane technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as unfavorable imaging of cell membranes, unfavorable development and use, background signal interference, etc., to achieve good photostability, easy to use Modified effect of biocompatibility and high sensitivity

Active Publication Date: 2020-04-28
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, some probes targeting cell membranes have been reported, such as Dio, Dil, DiD, DiR, etc. Coincidentally, these molecules all contain a longer alkane chain structure to increase the hydrophobicity of the molecule itself, so that when imaging cell membranes Embedded into the interior of the phospholipid bilayer membrane, however, it will inevitably generate strong background signal interference at the same time, thereby reducing the signal-to-noise ratio, which is not conducive to imaging the cell membrane. Enters the cell over time, so not suitable for long-term real-time imaging of cell membranes
In addition, some cell membrane probes that have not yet been commercially applied have been reported. These probes are often wrapped with long-chain PEG structures or modified with antibodies targeting certain receptors on the cell membrane, which makes the design process cumbersome and requires many synthesis steps. , which is not conducive to its reasonable development and use

Method used

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  • Targeted cell membrane surface GABA receptor fluorescent probe and preparation method and application thereof
  • Targeted cell membrane surface GABA receptor fluorescent probe and preparation method and application thereof
  • Targeted cell membrane surface GABA receptor fluorescent probe and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation process of the GABA receptor fluorescent probe targeting the cell membrane surface of this embodiment is as follows:

[0030]

[0031] The specific preparation method is:

[0032] Accurately weigh 0.0025 mol each of 4-(diethylamino)salicylaldehyde and 4,6-dihydroxy-2-mercaptopyrimidine into a dry round-bottomed flask, then add 10 mL of concentrated sulfuric acid and mix well, and place in an oil bath at 90 °C Condensate and reflux for 6 h under the condition, after cooling to room temperature, add an appropriate amount of ice cubes to dilute, add perchloric acid solution drop by drop under stirring conditions, and then filter with suction to obtain the crude product reddish-brown solid, wash the obtained solid with absolute ethanol Operation to purify it. Finally, the mass of the solid product obtained was 0.5721 g, so the product yield was 76%. The H NMR spectrum of the product probe is as Figure 9 Shown; C NMR spectrum as Figure 10 shown.

Embodiment 2

[0034] The preparation process of the GABA receptor fluorescent probe targeting the cell membrane surface of this embodiment is as follows:

[0035]

[0036] The specific preparation method is:

[0037] Accurately weigh 0.0025 mol of 4-(diethylamino) salicylaldehyde and 0.00266 mol of 4,6-dihydroxy-2-mercaptopyrimidine into a dry round bottom flask, then add 10 mL of concentrated sulfuric acid and mix well, 90 Condensate and reflux in an oil bath at ℃ for 6 h, cool to room temperature, add an appropriate amount of ice cubes for dilution, add perchloric acid solution drop by drop under stirring conditions, and then filter with suction to obtain a reddish-brown solid as a crude product, which is washed with anhydrous It is purified by washing operations with ethanol. The mass of the finally obtained solid product was 0.6022 g, so the product yield was 79.8%.

[0038] Example of implementation effect

[0039] 1. The fluorescence spectrum of the probe in PBS buffer (10 mM, p...

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Abstract

The invention belongs to the field of preparation of cell membrane surface GABA receptor fluorescent probes, relates to application of coumarin derivatives as cell membrane surface GABA receptor fluorescent probes, in particular to a targeted cell membrane surface GABA receptor fluorescent probe and a preparation method and application thereof. The structural formula of the fluorescent probe is shown in the specification. The probe is easy to synthesize, high in yield, capable of quickly targeting receptors of corresponding cell membranes, good in specificity, high in signal-to-noise ratio andcapable of targeting the cell membranes for a long time. In a confocal imaging experiment, the probe can well target a GABA receptor on the surface of the cell membrane.

Description

technical field [0001] The invention belongs to the field of preparation of fluorescent probes for GABA receptors on the surface of cell membranes, and relates to the application of coumarin derivatives as fluorescent probes for GABA receptors on the surface of cell membranes, in particular to a fluorescent probe targeting GABA receptors on the surface of cell membranes and its Preparation methods and applications. Background technique [0002] The surface cell membrane is mainly a semipermeable membrane composed of phospholipids. According to the composition structure, it can be roughly divided into glycerophospholipids, lipid rafts, and transmembrane ion channels. They wrap the cells and perform physiological functions such as selective absorption, exchange, and excretion of substances. Keep the cells in a relatively stable state as a whole, and then maintain normal life activities. Therefore, it is necessary to develop fluorescent probes targeting cell membranes and trac...

Claims

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Application Information

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IPC IPC(8): C07D491/052C09K11/06G01N21/64
CPCC07D491/052C09K11/06C09K2211/1048G01N21/6428G01N21/6486
Inventor 杨冉李朝辉孙远强王霞曾华金孟红敏屈凌波
Owner ZHENGZHOU UNIV
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