Lipid droplet specifically labeled fluorescent probe and synthesis method and application thereof

A technology of fluorescent probe and synthesis method, which is applied in the field of lipid droplet specific labeled fluorescent probe and its synthesis, can solve the problems to be further developed, and achieves good lipid droplet specific imaging ability, simple operation and simple preparation method. Effect

Pending Publication Date: 2021-01-05
WEST CHINA HOSPITAL SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although some lipid droplet fluorescent probes have been commercialized, the lipid droplet-specific imagi

Method used

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  • Lipid droplet specifically labeled fluorescent probe and synthesis method and application thereof
  • Lipid droplet specifically labeled fluorescent probe and synthesis method and application thereof
  • Lipid droplet specifically labeled fluorescent probe and synthesis method and application thereof

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Embodiment 1

[0037] A preferred embodiment of the present invention provides a method for synthesizing a lipid droplet-specifically labeled fluorescent probe. The specific steps are as follows:

[0038]

[0039] 4'-(diphenylamino)biphenyl-4-carbaldehyde (0.50g, 1.43mmol), 1,3-indandione (0.23g, 1.58mmol), dissolved in a mixed solution of 5mL methanol and 5mL toluene, Add 2 drops of piperidine, react at 100°C, monitor the reaction process by thin-layer chromatography, cool to room temperature after the reaction, concentrate, and separate and purify the product by silica gel column chromatography to obtain 0.56g reddish-brown solid compound, the yield was 81.96%. 1 H NMR (400MHz, CDCl 3 ):δ=7.05-7.11(t,2H),7.12-7.20(m,6H),7.27-7.33(m,4H),7.55-7.60(d,2H),7.71-7.76(d,2H),7.79 -7.85(m,2H),7.92(s,1H),7.99-8.05(m,2H)ppm.

Embodiment 2

[0041] A preferred embodiment of the present invention provides a method for synthesizing a lipid droplet-specifically labeled fluorescent probe. The specific steps are as follows:

[0042]

[0043] 5-(4-(diphenylamino)phenyl)thiophene-2-carbaldehyde (0.50g, 1.41mmol), 1,3-indandione (0.22g, 1.51mmol), dissolved in 5mL methanol and 5mL toluene Add 2 drops of piperidine to the mixed solution, react at 120°C, monitor the reaction process by thin-layer chromatography, cool to room temperature after the reaction, concentrate, and separate and purify the product by silica gel column chromatography to obtain 0.58 g of reddish-brown solid compound with a yield of 85.29%. 1 H NMR (400MHz, CDCl 3 ):δ=6.97-7.02(m,2H),7.11-7.19(m,6H),7.35-7.42(t,4H),7.68-7.71(d,1H),7.74-7.79(m,2H),7.88 -7.96(m,4H),8.05(s,1H),8.23-8.27(d,2H)ppm.

Embodiment 3

[0045] A preferred embodiment of the present invention provides a method for synthesizing a lipid droplet-specifically labeled fluorescent probe. The specific steps are as follows:

[0046]

[0047]5-(4-(xylylamino)phenyl)thiophene-2-carbaldehyde (0.60g, 1.56mmol), 1,3-indandione (0.25g, 1.72mmol), dissolved in 10mL of toluene, added 2 drops of piperidine were reacted at 120°C, and the reaction process was monitored by thin-layer chromatography. After the reaction was completed, it was cooled to room temperature, concentrated, and the product was separated and purified by silica gel column chromatography to obtain 0.60 g of a reddish-brown solid compound. The yield was 75.01%. 1 H NMR (400MHz, DMSO-d 6 ):δ=2.30(s,6H),6.90-6.94(d,2H),7.01-7.06(d,4H),7.25-7.23(d,4H),7.64-7.68(d,1H),7.68-7.74 (d,2H),7.87-7.97(m,4H),8.03(s,1H),8.22-8.26(d,2H)ppm.

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Abstract

The invention discloses a lipid droplet specifically labeled fluorescent probe and a synthesis method and application thereof. The synthesis method comprises the following steps: aromatic aldehyde compounds and 1,3-indandione react for 0.1-300 h in an organic solvent at the temperature of 50-140 DEG C in the presence of a catalyst, cooling is conducted to the room temperature, dichloromethane is added, filtering is conducted, pressure is reduced to remove the solvent, a product is separated and purified and drying is conducted to obtain the fluorescent probe. The fluorescent probe provided bythe invention has no fluorescence in an aqueous solution, almost has no fluorescence in a common organic solvent, has significantly enhanced fluorescence in grease, can be specifically targeted to lipid droplets in cells, and can be used for cell imaging of lipid droplets.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and in particular relates to a lipid droplet-specifically labeled fluorescent probe as well as its synthesis method and application. Background technique [0002] Fluorescence imaging provides an intuitive and real-time observation method for studying complex biological structures and physiological processes. As an important carrier of fluorescence imaging, organic fluorescent probes play an important role in the study of organelles and cell physiological processes. Although many fluorescent probes targeting mitochondria, lysosomes, endoplasmic reticulum and other organelles have been commercialized, there are still few fluorescent probes for lipid droplet imaging. Moreover, the imaging effect of commercial lipid droplet fluorescent probes is still unsatisfactory. On the one hand, traditional fluorescent probes are difficult to achieve long-term imaging observation due to their poor photost...

Claims

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Application Information

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IPC IPC(8): C07C225/22C07C221/00C07D333/22C09K11/06G01N21/64
CPCC07C225/22C07D333/22C09K11/06G01N21/6428C09K2211/1092C09K2211/1007C09K2211/1011C09K2211/1014
Inventor 陈茂廖延标庄伟华李淑芬
Owner WEST CHINA HOSPITAL SICHUAN UNIV
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