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Fluorescent probe for detecting polarity of lipid droplets and preparation method and application thereof

A fluorescent probe, lipid droplet technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of invasive operation, inconvenient wide application, etc., achieve high yield, good polarity specificity Sexually responsive, step-by-step effect

Inactive Publication Date: 2018-11-16
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the diagnosis of cancer by tumor markers has become a hotspot. Although some existing tumor markers have greatly improved the diagnosis rate of cancer, their widespread application is limited due to their invasiveness and inconvenient operation.

Method used

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  • Fluorescent probe for detecting polarity of lipid droplets and preparation method and application thereof
  • Fluorescent probe for detecting polarity of lipid droplets and preparation method and application thereof
  • Fluorescent probe for detecting polarity of lipid droplets and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1 Synthesis of fluorescent probe EBMC

[0041] (1) Synthesis of compound (3)

[0042]

[0043] Add 2.46 g of 3-bromocarbazole (10 mmol) (1) and 0.8 g of sodium hydroxide (20 mmol) into a high-pressure tube containing 20 mL of tetrahydrofuran, stir at room temperature, and add 6.56 g of bromoethane (60 mmol ), reacted for about 12h, after the reaction was completed, the system after the reaction was distilled under reduced pressure, and the solvent was spin-dried to obtain the crude product, and the mobile phase was separated and purified by column chromatography with ethyl acetate and petroleum ether at a volume ratio of 1:30 to obtain 3-Bromo-9-ethylcarbazole (3);

[0044] (2) Synthesis of compound (5):

[0045]

[0046] Weigh 0.274 g 3-bromo-9-ethylcarbazole (3) (1 mmol), 0.18 g 4-formylphenylboronic acid (4) (1.2 mmol), 37 mg tetrakis-(triphenylphosphine palladium) (0.03 mmol ), 0.445g potassium carbonate (3.23 mmol) in the mixed solvent of tetrahydr...

Embodiment 2

[0053] Example 2 Emission spectra of fluorescent probes in different solvents

[0054] A test mother solution of dimethyl sulfoxide (DMSO) with a concentration of 1 mM fluorescent probe EBMC obtained in Example 1 was prepared for use.

[0055] In the test solution, take 3 mL solvents of different polarities: toluene (Toluene), dioxane (Dioxane), tetrahydrofuran (THF), dichloromethane (DCM), acetone (Acetone), dimethyl sulfoxide ( DMSO), then add the probe mother solution with a concentration of 1mM, so that the final concentration of the probe in the test solution is 10 μM, and then perform fluorescence scanning (excitation wavelength 455nm, detection band 450-800nm) to obtain the fluorescence intensity in each system, such as image 3 shown. Depend on image 3 It can be seen that as the polarity of the solvent increases, the spectrum red shifts. Before the tetrahydrofuran solution, the fluorescence intensity increases with the increase of the polarity; after the tetrahydrof...

Embodiment 3

[0056] Example 3 Co-localization of fluorescent probes and commercial lipid droplet dyes

[0057] Preparation concentration is the test mother solution of the dimethyl sulfoxide (DMSO) of fluorescent probe EBMC obtained in embodiment 1 of 1 mM stand-by; The test mother liquor of sulfoxide (DMSO) is ready for use.

[0058] Inoculate an appropriate density of mouse mammary tumor cell 4T1 into a sterilized 35 mm imaging culture dish in CO 2 Incubator (at 37°C, 5% CO 2 ), after the cells were attached to the wall, the fluorescent probe EBMC and the lipid droplet commercial dye Nile Red were added to the cells at the same time, so that the final concentration of the fluorescent probe was 10 μM, and the final concentration of Nile Red was 5 μM. Half an hour later, discard the medium, wash the cells with PBS buffer three times, and then perform fluorescence imaging (excitation wavelength: 488 nm, green channel 500-550nm; excitation wavelength: 561nm, red channel 570nm-620nm), the i...

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Abstract

The invention provides a fluorescent probe for detecting the polarity of a lipid droplet. The chemical name is 3-(4-(2,2-dicyanylvinyl)phenyl)-9-ethylcarbazole, and the structural formula is as shownin the specification. Due to the intramolecular distorted electron transfer effect (TICT) of the probe, a good response to solvent polarity is achieved. The fluorescent probe of the invention is electrically neutral, and can be well positioned in lipid droplets in cells. The probe can be accurately located in lipid droplets, has high sensitivity, good optical stability and specific response to polarity, and achieves detection of polarity of lipid droplets in cells. A method for synthesizing the probe has the advantages of simple steps, convenient purification and high yield.

Description

technical field [0001] The invention belongs to the field of small organic molecule fluorescent probes, and in particular relates to a fluorescent probe for detecting lipid droplet polarity, a preparation method and application thereof. Background technique [0002] Cancer is one of the terminal diseases recognized all over the world, and a large number of people die of cancer every year. Although cancer is an important disease, cancer mortality is manageable if we diagnose and treat it in time. At present, the diagnosis of cancer by tumor markers has become a hotspot. Although some existing tumor markers have greatly improved the diagnosis rate of cancer, their widespread application is limited due to their invasiveness and inconvenient operation. Therefore, the development of new tumor markers is of great significance to the diagnosis and treatment of cancer. In recent years, lipid droplets have attracted extensive attention due to their unique structures and properties....

Claims

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Application Information

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IPC IPC(8): C07D209/86C09K11/06G01N21/64
CPCC07D209/86C09K11/06C09K2211/1007C09K2211/1029G01N21/6428G01N21/6486
Inventor 林伟英阴军玲彭敏
Owner UNIV OF JINAN
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