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Near-infrared fluorescent compound with targeting function and application thereof

A technology of fluorescent compounds and compounds, applied in the fields of organic chemistry, fluorescence/phosphorescence, luminescent materials, etc., can solve the problems of fine research on the microstructure of difficult organisms, lack of functional dye compounds, and difficult super-resolution imaging.

Active Publication Date: 2021-08-24
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the dye compounds reported in recent years have the function of target labeling, but the short fluorescence wavelength is difficult to be used for super-resolution imaging
However, near-infrared dyes can be used for super-resolution imaging but do not have targeting or labeling functions. Some near-infrared dyes have poor imaging stability and are difficult to apply to fine research on the microstructure of living organisms.
Therefore, there is currently a lack of functional dye compounds that have both labeling and targeting functions and near-infrared absorption and emission for super-resolution imaging research.

Method used

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  • Near-infrared fluorescent compound with targeting function and application thereof
  • Near-infrared fluorescent compound with targeting function and application thereof
  • Near-infrared fluorescent compound with targeting function and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] i) Under argon, A (2.97 mmol), Pd(OAc) 2 (0.45 mmol), BINAP (0.32 mmol), Cs 2 CO 3 (8.62 mmol) and pyrrolidine (1.2 mL) were dissolved in toluene and reacted with stirring at 110°C. The reaction was monitored by TLC until the reaction was complete. After cooling to room temperature, the reaction mixture was washed with water and evaporated. The crude product was purified by silica gel column chromatography (ethyl acetate / hexane = 1 / 25) to obtain pale yellow solid B1.

[0033] ii) Use a water separator to remove water, stir the mixture of compound B1 (0.94 mmol), ethylene glycol (2 mL), and TsOH (0.29 mmol), react at 150 ° C, monitor the reaction with TLC until the reaction of compound B1 is complete. The reaction mixture was concentrated and purified by silica gel column chromatography to obtain pale yellow solid C1.

[0034] iii) Compound C1 (0.91 mmol) was added to 5 mL of DMF and stirred at room temperature. NBS (1.82 mmol) was added to the reaction...

Embodiment 2

[0038]

[0039] i) Under argon, A (2.97 mmol), Pd(OAc) 2 (0.45 mmol), BINAP (0.32 mmol), Cs 2 CO 3 (8.62 mmol) and diethylamine (1.3 mL) were dissolved in toluene and reacted with stirring at 120°C. The reaction was monitored by TLC until the reaction was complete. After cooling to room temperature, the reaction mixture was washed with water and evaporated. The crude product was purified by silica gel column chromatography (ethyl acetate / hexane = 1 / 25) to obtain light yellow solid B2.

[0040] ii) Use a water separator to remove water, stir the mixture of compound B2 (0.94 mmol), ethylene glycol (2 mL), and TsOH (0.29 mmol), react at 150 ° C, monitor the reaction with TLC until the reaction of compound B2 is complete. The reaction mixture was concentrated and purified by silica gel column chromatography to obtain light yellow solid C2.

[0041] iii) Compound C2 (0.91 mmol) was added to 5 mL of DMF and stirred at room temperature. NBS (1.82 mmol) was added to the react...

Embodiment 3

[0045]

[0046] i) Under argon, A (2.97 mmol), Pd(OAc) 2 (0.45 mmol), BINAP (0.32 mmol), Cs 2 CO 3 (8.62 mmol) and cyclohexylamine (1.4 mL) were dissolved in toluene, and the reaction was stirred at 115°C, and the reaction was monitored by TLC until the end of the reaction. After cooling to room temperature, the reaction mixture was washed with water and evaporated. The crude product was purified by silica gel column chromatography (ethyl acetate / hexane = 1 / 25) to obtain pale yellow solid B3.

[0047] ii) Use a water trap to remove water, stir a mixture of compound B3 (0.94 mmol), ethylene glycol (2.1 mL), and TsOH (0.29 mmol), react at 150°C, and monitor the reaction with TLC until compound B3 is completely reacted. The reaction mixture was concentrated and purified by silica gel column chromatography to obtain light yellow solid C3.

[0048] iii) Compound C3 (0.91 mmol) was added to 5 mL of DMF and stirred at room temperature. NBS (1.82 mmol) was added to the reactio...

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Abstract

The invention discloses a near-infrared fluorescent compound with a targeting function and an application thereof, and belongs to the field of fine chemical engineering. According to the near-infrared fluorescent compound with the targeting function, groups with mitochondria, cell membrane and protein marking functions are respectively connected to a long-wavelength fluorescent chromophore; and the invention initiatively provides the fluorescent compound which has a targeted cell microstructure function, has near-infrared absorption and emission spectrum and can be used for super-resolution imaging. The problem that a traditional fluorophore cannot mark mitochondria, cell membranes and protein is solved; and meanwhile, the problem that cells are seriously damaged in the imaging process due to the fact that the excitation light wavelength is short is solved, and more selectable tools are provided for biological cell nucleus imaging.

Description

technical field [0001] The invention relates to a class of near-infrared fluorescent compounds with targeting functions and applications thereof, belonging to the field of fine chemicals. Background technique [0002] Fluorescence imaging technology is widely used in various fields such as life science, medicine, chemistry, etc., especially in the field of life science, it has been significantly developed. Modern fluorescence imaging, super-resolution fluorescence imaging, and fluorescence detection technologies put forward new requirements for fluorophores, such as near-infrared fluorescence emission, large molar extinction coefficient, and high fluorescence quantum yield. Due to its long absorption and emission wavelengths, near-infrared fluorophores have better biocompatibility than fluorophores in the visible region, and the imaging depth is greater than that of dyes in the visible region. They can provide additional imaging windows and cooperate with other dyes to achie...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/10C07D409/10C07D411/10C09K11/06G01N21/64
CPCC07D405/10C07D409/10C07D411/10C09K11/06G01N21/6428C09K2211/1029C09K2211/1059C09K2211/1088C09K2211/1044C09K2211/1033C09K2211/1092C09K2211/1096
Inventor 肖义张新富陈令成
Owner DALIAN UNIV OF TECH
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