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A kind of near-infrared lysosome fluorescent indicator and its application

A fluorescent indicator and lysosome technology, applied in the direction of fluorescence/phosphorescence, luminescent materials, material analysis through optical means, etc., can solve unfavorable and accurate imaging, difficult two-color and multi-color multi-channel fluorescence imaging, spectral overlap Advanced problems, to achieve the effect of strong luminous brightness, high molar extinction coefficient, and high fluorescence quantum yield

Active Publication Date: 2022-06-07
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, more fluorescent indicators targeting lysosomes have been reported successively, but the emission peaks of most fluorescent dyes are in the visible light range (400-650nm), and the fluorescent indicators in the ultraviolet region are compatible with intracellular Autofluorescence overlaps, which is not conducive to accurate imaging; while most recently reported lysosomal probes and commercial lysosomal indicators are concentrated in the visible region, the spectral overlap between the probes is high, and it is difficult to meet two-color and more colors Multi-channel fluorescence imaging of

Method used

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  • A kind of near-infrared lysosome fluorescent indicator and its application
  • A kind of near-infrared lysosome fluorescent indicator and its application
  • A kind of near-infrared lysosome fluorescent indicator and its application

Examples

Experimental program
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Effect test

Embodiment 1

[0024]

[0025] i) A1 (1.27 mmol) and B (1.27 mmol) were stirred in 30 mL of dry toluene (water was removed with molecular sieves before use), 1 mL of piperidine and 1 mL of glacial acetic acid were added for catalysis, and the water was heated to reflux at 150°C. The portion is removed with a water separator. The reaction was monitored by TLC until the end of the reaction. After cooling to room temperature, most of the toluene in the reaction solution was removed under reduced pressure, and the resulting solution was diluted with dichloromethane, washed with water and concentrated. The crude product was purified by silica gel column chromatography (dichloromethane / petroleum ether=1 / 3) to obtain solid C1.

[0026] ii) Under argon, compounds C1 (82 μmol), Y1 (164 μmol), CuSO 4 ·5H 2 O (82 μmol), sodium ascorbate (164 μmol) was added to a mixed solution of toluene, ethanol and water (v / v / v=12 / 4 / 1), the reaction was stirred at room temperature, and the reaction was monitore...

Embodiment 2

[0028]

[0029] Refer to Example 1 for the synthesis methods of compounds D2, D3 and D4.

Embodiment 3

[0031]

[0032] i) A2 (1.27 mmol), B (1.27 mmol) were stirred in 30 mL of dry toluene (water was removed with molecular sieves before use), 1 mL of piperidine and 1 mL of glacial acetic acid were added for catalysis, and the water was heated to reflux at 150°C. The portion is removed with a water separator. The reaction was monitored by TLC until the end of the reaction. After cooling to room temperature, most of the toluene in the reaction solution was removed under reduced pressure, and the resulting solution was diluted with dichloromethane, washed with water and concentrated. The crude product was purified by silica gel column chromatography (dichloromethane / petroleum ether=1 / 3) to obtain solid C2.

[0033] ii) Under argon, compounds C2 (82 μmol), Y2 (164 μmol), CuSO 4 ·5H 2 O (82 μmol), sodium ascorbate (164 μmol) was added to a mixed solution of toluene, ethanol and water (v / v / v=12 / 4 / 1), the reaction was stirred at room temperature, and the reaction was monitored b...

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Abstract

A near-infrared lysosome fluorescent indicator and its application belong to the field of fine chemicals. The near-infrared lysosomal fluorescent indicator creatively introduces a hydrophilic small molecule group into the lipophilic BODIPY matrix structure, and successfully obtains a series of amphiphilic close IR BODIPY DERIVATIVES. This design makes the dye molecules non-fluorescent due to aggregation in aqueous solution, and recovers fluorescence due to de-aggregation in acidic lipid environment. At the same time, this type of compound is easy to penetrate the cell membrane, quickly targets the lysosome, and only emits fluorescence after entering the cell. Compared with other lysosome-targeting fluorescent dyes, it has the advantages of no washing and weak background fluorescence. In addition, the compound can be accurately labeled in lysosomes at concentrations as low as nanometers, and can be used for long-term fluorescence imaging studies to track the movement and morphological changes of lysosomes in real time for a long time.

Description

technical field [0001] The invention relates to a kind of near-infrared lysosome fluorescent indicator and application, and belongs to the field of fine chemical industry. Background technique [0002] Lysosomes play an important role in various life activities of cells, such as material metabolism, cell membrane circulation, and apoptosis. Lysosomes are highly dynamic in nature, constantly changing their morphology and spatial distribution. Visually tracking lysosomes and detecting their active species, specific microenvironments and key physiological processes will not only help to understand the molecular mechanism of lysosomes participating in life activities, but also have important guiding significance for the treatment of diseases. In order to realize the above functions, fluorescent probes with superior luminescence properties, high lysosome specificity, and little interference with lysosome physiological functions are required. In recent years, many fluorescent in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06G01N21/6428C09K2211/1055C09K2211/1007C09K2211/1029C09K2211/1059C09K2211/1044G01N2021/6417C07D517/14C07D209/58C09B23/04C09B57/00G01N21/64
Inventor 张新富李香丽肖义
Owner DALIAN UNIV OF TECH
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