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A Benzylidene Dione Compound and Its Preparation and Application in Lipid Droplet Specific Imaging

A technology of benzylidene indanedione and compound is applied in the application field of lipid droplet-specific fluorescence imaging, which can solve the problems of high cost, limited application, aggregation-induced quenching, etc., and achieves large Stokes shift and photostability. Strong, less cytotoxic effect

Active Publication Date: 2020-05-22
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to realize lipid droplet-specific fluorescence imaging, the following key issues need to be solved: (1) In order to achieve high-brightness fluorescence imaging of lipid droplets, fluorescent materials need to be aggregated in lipid droplets at high concentrations, however, the aggregation-induced quenching of traditional fluorescent materials The disadvantages of these severely limit their application in high-brightness lipid droplet fluorescence imaging; (2) in order to reduce production costs, it is necessary to develop easily prepared lipid droplet-specific fluorescent probes
However, traditional lipid droplet-specific fluorescent probes require multi-step synthesis, are difficult to prepare, and are expensive; (3) lipid droplet-specific fluorescent probes should have a large two-photon absorption cross-section in the near-infrared region. Photon-excited fluorescence imaging can effectively reduce background noise, reduce light damage, and improve deep penetration ability; (4) lipid droplet-specific fluorescent probe molecules should have rapid penetration ability of living cells, which is convenient for imaging applications; (5) Strong photostability, convenient for long-term continuous observation, however, traditional fluorescent materials are prone to photobleaching, making it difficult to use for continuous observation

Method used

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  • A Benzylidene Dione Compound and Its Preparation and Application in Lipid Droplet Specific Imaging
  • A Benzylidene Dione Compound and Its Preparation and Application in Lipid Droplet Specific Imaging
  • A Benzylidene Dione Compound and Its Preparation and Application in Lipid Droplet Specific Imaging

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Experimental program
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Effect test

Embodiment 1

[0052] Benzylidene indene dione compound IND-TPA: 2-(4-(Diphenylamino)benzylidene)-1H-indene-1,3(2H)-dione (R 1 = Hydrogen, R 2 = R 3 =phenyl) structural formula is as follows:

[0053]

[0054] The preparation method of above-mentioned benzylidene dione compound, comprises the following steps:

[0055] 4-Dianilinobenzaldehyde (273mg, 1.0mmol), 1,3-indanedione (146mg, 1.0mmol) and morpholine (85mg, 1.0mmol) were dissolved in 15mL of ethanol, followed by reflux reaction under nitrogen protection (reaction at 78° C. for 3 hours); after the reaction was completed, after returning to room temperature, vacuum drying was obtained after filtration to obtain a red solid product 2-(4-(diphenylamino)benzylidene)-1H-indene-1,3( 2H)-dione (285 mg, 71% yield). The relevant structural characterization data are as follows:

[0056] 1 H NMR (DMSO-d 6 ,500MHz):δ8.49(d,J=9.0Hz,2H),7.93–7.89(m,4H),7.71(s,1H),7.48–7.45(m,4H),7.30–7.26(m,6H ),6.85(d,J=9.0Hz,2H); 13 C NMR (CD 2 Cl 2 ,...

Embodiment 2

[0058] The photophysical property characterization of the compound IND-TPA prepared in embodiment 1:

[0059] tetrahydrofuran and water according to different volume ratios (tetrahydrofuran: water = 100:0, 90:10, 80:20, 70:30, 60:40, 50:50, 40:60, 30:70, 20:80, 10:90, 1:99) mixed to form water content (f w ) different mixed solutions, the compound IND-TPA was dissolved in these mixed solutions, so that the concentration of the compound was 10 -5 mol L -1 , then detect the fluorescence emission spectrum and the ultraviolet absorption spectrum in tetrahydrofuran, the results are shown in figure 1 . figure 1 For the ultraviolet absorption and fluorescence emission spectrogram of the compound IND-TPA prepared in embodiment 1; (A) the normalized ultraviolet absorption spectrogram of compound IND-TPA in tetrahydrofuran; (B) is the compound IND-TPA in tetrahydrofuran and water Fluorescence emission spectra of increasing water content in the mixed solution (10 - 5 mol L -1 ); (...

Embodiment 3

[0067] The cytotoxicity experiment of the compound IND-TPA prepared in embodiment 1:

[0068] The experimental results of the cytotoxicity of compound IND-TPA against lung cancer cells HCC827 and A549 are as follows: Figure 5 shown. The results indicated that the compound IND-TPA had almost no cytotoxicity at different concentrations (5, 10, 20, 40, 60, 80, 100 μM).

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Abstract

The invention belongs to the field of medical materials, and discloses a benzylidene indandione compound and a preparation thereof and an application in specific imaging of a lipid droplet. The structure of the benzylidene indandione compound is as shown in a formula I. The benzylidene indandione compound has the advantage of aggregation-induced emission, and the defects of aggregation-induced quenching of a traditional fluorescent dye can be effectively overcome, so that the specific fluorescence imaging of the lipid droplet in a living cell can be achieved; furthermore, the benzylidene indandione compound has a two-photon absorption cross-section which is high in living cell penetration rate, high in signal to noise ratio, small in cytotoxicity, large in stokes shift and large in near infrared region. The formula I is as shown in the specification.

Description

technical field [0001] The invention belongs to the field of medical materials, and in particular relates to a compound with aggregation-induced luminescent properties, a preparation method thereof, and an application in lipid droplet-specific fluorescence imaging. Background technique [0002] Lipid droplet is not only an important storage place for lipid molecules and proteins, but also a dynamically changing multifunctional organelle. Lipid droplet size and number vary widely in different cells. Since lipid droplets not only serve as energy storage, but also play an important role in physiological activities such as membrane synthesis and protein degradation, lipid droplets are closely related to many diseases, including cancer, inflammation, viral infection, and obesity. [0003] Cancer cells have the characteristics of rapid proliferation, so they have a high demand for lipid molecules such as fatty acids and phospholipids, and the corresponding lipid droplet content i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C221/00C07C225/22C09K11/06G01N21/64
CPCC07C225/22C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014G01N21/6486
Inventor 唐本忠高蒙秦安军
Owner SOUTH CHINA UNIV OF TECH