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A ratiometric fluorescent probe for distinguishing lipid droplets of different polarities and its preparation method and application

A technology of fluorescent probes and polar lipids, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of inability to distinguish lipid droplets of different polarities, and achieve good polarity-specific response, steps Simple, easy-to-purify effect

Inactive Publication Date: 2020-04-07
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the problem that existing probe pairs cannot distinguish lipid droplets of different polarities, the present invention provides a ratiometric fluorescent probe that can distinguish different polarities with sensitive response, low detection limit and good specificity, and has two-photon properties

Method used

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  • A ratiometric fluorescent probe for distinguishing lipid droplets of different polarities and its preparation method and application
  • A ratiometric fluorescent probe for distinguishing lipid droplets of different polarities and its preparation method and application
  • A ratiometric fluorescent probe for distinguishing lipid droplets of different polarities and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1 Synthesis of Fluorescent Probe CTPA

[0036] (1) Synthesis of compound (3):

[0037]

[0038] Add 1.93 g of NN-diethylaminosalicylaldehyde (10 mmol) (1) and 1.56 g of ethyl acetoacetate (12 mmol) into a flask filled with 20 mL of ethanol, after stirring evenly, add three drops of piperidine at room temperature After stirring overnight, a large amount of yellow solids precipitated out, filtered, washed with ethanol, added 90°C ethanol until just dissolved, recrystallized after cooling, and proceeded to the next step of reaction.

[0039] (2) Synthesis of compound (5):

[0040]

[0041] Weigh 0.59 g 3-acetyl-7 (diethylamino) coumarin (3) (1 mmol), add dropwise three drops of piperidine, and 0.273 g 4-dianilinobenzaldehyde (1 mmol) in the Compound (4) was mixed with ethanol and acetonitrile (1:1), heated to 80 °C and refluxed overnight, solids were precipitated, filtered under reduced pressure, and recrystallized with a mixture of ethanol and acetonitrile...

Embodiment 2

[0045] Example 2 Emission spectra of fluorescent probes in different solvents

[0046]A test mother solution of the fluorescent probe CTPA synthesized in Example 1 in dimethyl sulfoxide (DMSO) with a concentration of 1 mM was prepared for use.

[0047] In the test solution, take 3 mL solvents of different polarities: dioxane, ether, tetrahydrofuran (THF), dichloromethane (DCM), butanol, acetone, dimethyl sulfoxide (DMSO), and then add 30 μL of the probe mother solution, so that the concentration of the probe in the test solution is 10 μL, and perform fluorescence scanning (excitation wavelength 455nm, detection band 450-750nm). The fluorescence intensity in each system was obtained. like Figure 4 As shown, as the solvent polarity increases, the spectrum red shifts and the fluorescence intensity becomes weaker.

Embodiment 3

[0048] Example 3 Selectivity of Fluorescent Probes to Different Molecules or Ions

[0049] A test mother solution of the fluorescent probe CTPA synthesized in Example 1 in dimethyl sulfoxide (DMSO) with a concentration of 1 mM was prepared for use. Prepare Fe at a concentration of 200 μM 2+ , H 2 o 2 , Gys, Gin, GSH, Ser, Thr, Asn, ClO - , Dioxane solution, set aside.

[0050] Add 30 μL of probe mother solution to 3 mL of the solution prepared above to ensure that the final concentration of the solution to be tested is 10 μM, then shake well, and perform emission spectrum detection (excitation wavelength 455nm, detection band 450-750nm). The ratio of the measured fluorescence intensity to the fluorescence intensity of dioxane (I / I 二氧六环 ) is the ordinate, and different molecules or ions are used as the abscissa to make a histogram, such as Figure 5 . Depend on Figure 5 It can be seen that the fluorescent probe has strong fluorescence in dioxane solution; the fluoresce...

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Abstract

The invention provides a ratio type fluorescent probe for distinguishing lipid droplets with different polarities. A chemical name is (E)-7-(N,N-diethylamino)-3-(3-(4-(diphenylamine)phenyl)acrylyl-2H-benzopyrone; N,N-diethylamino salicylic aldehyde reacts with ethyl acetoacetate to generate 3-acetyl-7-(diethylamino)coumarin; the product reacts with 4-(N,N-Diphenylamino)benzaldehyde (4) to obtain the fluorescent probe. The fluorescent probe has a two-photon property and an aggregation-induced light-emitting property; a whole body of the probe is electrically neutral and can be positioned in thelipid droplets with the different polarities very well. The probe has low toxicity, good optical stability and specific response on the polarities; detection on the polarities of the lipid droletps in organs and living bodies is realized. The invention further provides a synthesis method of the probe; the synthesis method has the advantages of simple steps, convenient for purification and high yield.

Description

technical field [0001] The invention relates to a ratio-type fluorescent probe for distinguishing lipid droplets of different polarities, a preparation method and application thereof, and belongs to the field of organic small molecule fluorescent probes. Background technique [0002] Lipid droplets are composed of phospholipid monolayers and a hydrophobic core composed of neutral lipids, and there are many proteins distributed on the surface. For a long time, lipid droplets have been considered as a particle similar to glycogen, which is only used to store energy. When cells When energy is needed, it is used to supply energy. It is an "inert" cell inclusion, so lipid droplets have not been valued by people for a long time. In recent years, the research on lipid droplets has developed rapidly. Studies have shown that lipid droplets are not a simple energy storage in cells, but a complex, active and dynamically changing multifunctional organelle. The metabolism of lipid drop...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06C09K2211/1007C09K2211/1014C09K2211/1088G01N21/6486
Inventor 林伟英阴军玲彭敏
Owner UNIV OF JINAN
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