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Lysosome targeted fluorescent substance and synthesis method thereof

A technology of fluorescent substances and lysosomes, applied in the fields of biochemical equipment and methods, fluorescence/phosphorescence, chemical instruments and methods, etc., can solve the problems of small scope, easily inactivated antibodies, high price, etc., and achieve stable product properties, Simple synthetic route and high yield effect

Inactive Publication Date: 2011-02-02
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A dye will have photobleaching and phototoxicity. Under the irradiation of ultraviolet and visible light, it will lose its fluorescence activity in a short period of time, or produce singlet oxygen and other substances that are easily toxic to living cells, which is not conducive to the non-damage of living cells. Imaging; although antibodies are low in toxicity, their high price and easy inactivation limit the application of antibodies in cell imaging
Moreover, the range of options for dyes and antibodies is relatively small, which cannot meet the needs of scientific research and practical applications in terms of fluorescence excitation and emission ranges or organelle targeting.

Method used

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  • Lysosome targeted fluorescent substance and synthesis method thereof
  • Lysosome targeted fluorescent substance and synthesis method thereof
  • Lysosome targeted fluorescent substance and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Example 1: Synthesis of intermediate 5,11-dibromo-[1,5-diazaocine]diazaoctene tetraene:

[0026] 6.9g of 4-bromoaniline and 2.4g of paraformaldehyde (n=30) were mixed and placed in a 250mL long-necked flask, a magnetic stirrer was added, and the reaction system was cooled to -20°C in a cold trap. Under the condition of magnetic stirring, 80 mL of trifluoroacetic acid was slowly added dropwise to the system with a 100 mL constant pressure dropping funnel, and the trifluoroacetic acid was completely added dropwise in about 50 minutes. After the 4-bromoaniline and paraformaldehyde in the reaction system were completely dissolved, the temperature of the system was raised to 0° C., and the reaction was continued for 140 hours. After finishing the reaction, dissolve the solid solution with sodium hydroxide (NaOH) to form a 1mol / L solution. The reacted solution was slowly added dropwise into the sodium hydroxide solution while stirring, and a large amount of solids were preci...

Embodiment 2

[0027] Example 2: Synthesis of intermediate 5,11-dibromo-[1,5-diazaocine]diazacyclooctene tetraene

[0028] 6.9g of 4-bromoaniline and 3.0g of paraformaldehyde (n=30) were mixed and placed in a 250mL long-necked flask, and a magnetic stirrer was added to react at room temperature. Under the condition of magnetic stirring, 80 mL of trifluoroacetic acid was slowly added dropwise to the system with a 100 mL constant pressure dropping funnel, and the trifluoroacetic acid was completely added dropwise in about 50 minutes. 4-bromoaniline and paraformaldehyde in the reaction system were completely dissolved, and the reaction was continued for 140 hours. After finishing the reaction, dissolve the solid solution with sodium hydroxide (NaOH) to form a 1mol / L solution. The reacted solution was slowly added dropwise into the sodium hydroxide solution while stirring, and a large amount of solids were precipitated. After the dropwise addition, the pH of the solution was about 8, and it wa...

Embodiment 3

[0029] 6.9 g of 4-bromoaniline and 2.4 g of paraformaldehyde (n=30) were mixed and placed in a 250 mL long-necked flask, and a magnetic stirring bar was added. Under the condition of -20°C and magnetic stirring, 80 mL of trifluoroacetic acid was slowly added dropwise to the system with a 100 mL constant pressure dropping funnel, and the trifluoroacetic acid was completely added dropwise in about 50 minutes. The 4-bromoaniline and paraformaldehyde in the reaction system were completely dissolved, and the reaction was continued at 0° C. for 70 hours. After finishing the reaction, dissolve the solid solution with sodium hydroxide (NaOH) to form a 1mol / L solution. The reacted solution was slowly added dropwise into the sodium hydroxide solution while stirring, and a large amount of solids were precipitated. After the dropwise addition, the pH of the solution was about 7, extracted with 100mL of chloroform, extracted continuously for 3 times, and combined the organic phases. Rota...

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Abstract

The invention relates to a lysosome targeted fluorescent substance of which the structural formula is shown in the specifications. The synthesis method of the compound comprises the following steps: taking trifluoroacetic acid as a solvent and a reaction catalyst, enabling 4-bromaniline and paraformaldehyde to react to generate a bromine-substituted intermediate product, and then, carrying out Heck reaction to substitute bromine by 4-vinyl-N,N-dimethyl benzylamine. The method of the invention effectively applies the Heck reaction and has simple synthesis paths and higher yield, and the obtained product has stable properties and has the functions of fluorescence emission of visible light and lysosome targeting.

Description

technical field [0001] The invention relates to a lysosome-targeted fluorescent substance and a synthesis method thereof, belonging to the field of cell imaging. Background technique [0002] The development of modern cell micro-optical imaging technology and the fine function research of organelles requires the development and application of fluorescent reagents with high efficiency, high sensitivity and organelle targeting. Microscopic imaging of cells and organelles, and even the visual dynamic labeling of organelles' fine functions, has always been the focus and difficulty of modern microscopic imaging. It provides intuitive scientific basis for various human diseases and cell aging, and has extremely important biological significance and The value of new drug development. [0003] Organelles generally do not have clear and effective targets, and small chemical molecules capable of targeting specific organelles are rare. At present, this field is becoming a research ho...

Claims

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Application Information

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IPC IPC(8): C07D487/08C09K11/06C12N5/00G01N21/64
Inventor 周翔吴志国田沺翁小成
Owner WUHAN UNIV
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