Lipid droplet targeted fluorescent dye as well as preparation method and application thereof

A technology of fluorescent dyes and lipid droplets, applied in the field of nanomedicine, can solve the problems of complex preparation process and achieve the effect of simple steps, high purity, and convenient industrial production

Active Publication Date: 2021-06-29
SHENZHEN INST OF ADVANCED TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation process of most reported AIE fluorescent dyes is complicated. Most AIE fluorescent dyes target mitochondria, endoplasmic reticulum, lysosome, etc., so there is an urgent need for effective lipid droplet targeting and simple preparation methods. , AIE fluorescent dye with high purity, high efficiency and low cost

Method used

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  • Lipid droplet targeted fluorescent dye as well as preparation method and application thereof
  • Lipid droplet targeted fluorescent dye as well as preparation method and application thereof
  • Lipid droplet targeted fluorescent dye as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 Preparation of the lipid droplet targeting fluorescent probe of the present invention

[0040] 24.2 mg 0.1 mmol of 1,3-bis(dicyanomethylene)indan and 36.1 mg 0.12 mmol of 4-[bis(4-methylphenyl)amino]benzaldehyde were dissolved in 1 mL of acetic anhydride. Then the mixture was heated to 60°C for 4 hours. The solvent was evaporated in vacuo, and the residue was purified by recrystallization from a mixed solution of dichloromethane and n-hexane (the volume ratio of dichloromethane and n-hexane was 1:10) to obtain pure MeTIND-4.

Embodiment 2

[0041] Example 2 Preparation of the lipid droplet targeting fluorescent probe of the present invention

[0042] 24.2 mg 0.1 mmol of 1,3-bis(dicyanomethylene)indan and 361 mg 0.12 mmol of 4-[bis(4-methylphenyl)amino]benzaldehyde were dissolved in 50 mL of acetic anhydride. Then the mixture was heated to 50°C for 3 hours. The solvent was evaporated in vacuo, and the residue was purified by recrystallization from a mixed solution of dichloromethane and n-hexane (the volume ratio of dichloromethane and n-hexane was 1:10) to obtain pure MeTIND-4.

Embodiment 3

[0043] Example 3 Preparation of the lipid droplet targeting fluorescent probe of the present invention

[0044] 24.2 mg 0.1 mmol of 1,3-bis(dicyanomethylene)indan and 722 mg 0.12 mmol of 4-[bis(4-methylphenyl)amino]benzaldehyde were dissolved in 500 mL of acetic anhydride. Then the mixture was heated to 70°C for 5 hours. The solvent was evaporated in vacuo, and the residue was purified by recrystallization from a mixed solution of dichloromethane and n-hexane (the volume ratio of dichloromethane and n-hexane was 1:10) to obtain pure MeTIND-4.

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Abstract

The invention discloses a lipid droplet targeting fluorescent dye as well as a preparation method and an application thereof, and the preparation method comprises the following steps: carrying out a simple reaction on 1,3-bis (dicyanomethylene)indan and 4-[bis(4-methylphenyl)amino]benzaldehyde, and carrying out recrystallization purification to obtain pure 2, 2'-(2-(4-(di-p-methylphenyl amino) benzylidene)-1H-indene-1, 3(2H)-dialkylene) dimethyl nitrile in the formula (I). The preparation method is simple, the fluorescent dye can be obtained in one step, almost no by-product exists, the efficiency is high, the cost is low, and the fluorescent dye has the potential of large-scale preparation, and the prepared lipid droplet targeted fluorescent dye can be used for monitoring the dynamic change of lipid droplets in cells and can be used for distinguishing immune cells from tumor cells.

Description

technical field [0001] The invention relates to the technical field of nanomedicine, in particular to a lipid droplet targeting fluorescent dye and its preparation method and application. Background technique [0002] The shortcomings of traditional fluorescent materials due to aggregation-induced quenching (ACQ) limit their application at high concentrations, which in turn affects the sensitivity of the probe. Aggregation-induced emission (AIE) molecules are different from traditional fluorescent molecules. Traditional fluorescent molecules will weaken their fluorescence intensity or even not emit light in a high concentration state, while AIE molecules will become more luminescent as they aggregate. This is mainly because AIE molecules within a certain space range The self-rotation is restricted, which suppresses the excited state energy emitted in a non-radiative form, opens the channel for radiative decay, and thus enhances the fluorescence. AIE probes can continuously ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/04C09B23/14C09K11/06G01N21/64
CPCC09B23/04C09B23/14C09K11/06G01N21/6428G01N21/6458C09K2211/1007C09K2211/1011C09K2211/1014
Inventor 张鹏飞徐秀丽蔡林涛龚萍罗媛
Owner SHENZHEN INST OF ADVANCED TECH
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