Lysosome fluorescent probe based on chalcone as well as preparation method and application of lysosome fluorescent probe

A technology of fluorescent probes and lysosomes, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of cumbersome preparation process, high cost, complex structure, etc., and achieve simple preparation method, low cost, The effect of high degree of matching

Pending Publication Date: 2022-05-13
SHAANXI UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Some commercial organic molecular fluorescent probes have been widely used in targeted fluorescence imaging of intracellular lysosomes. However, many commercial lysosomal fluorescent probes have complex structures, cumbersome preparation processes, and high costs.

Method used

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  • Lysosome fluorescent probe based on chalcone as well as preparation method and application of lysosome fluorescent probe
  • Lysosome fluorescent probe based on chalcone as well as preparation method and application of lysosome fluorescent probe
  • Lysosome fluorescent probe based on chalcone as well as preparation method and application of lysosome fluorescent probe

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preparation example Construction

[0032] A preparation method of a chalcone-based lysosome fluorescent probe provided by the invention comprises the following steps:

[0033] Step 1) Add HCA and 1,3-dibromopropane into an organic solvent and mix evenly. The molar ratio of the reaction raw material HCA to 1,3-dibromopropane is 1:2~10. The molar ratio of bromopropane to organic solvent is 1:2~10:60~1000. Under alkaline conditions, heat to 60-120°C, reflux and stir for 4~24h, the reaction raw materials HCA, 1,3-dibromopropane The molar ratio of base to base is 1:2~10:1~10, the solid residue is removed by filtration, the solvent is distilled off under reduced pressure, and the crude product is separated by silica gel column chromatography to obtain the intermediate Br-HCA. The reaction formula is as follows:

[0034]

[0035] Step 2) Add the intermediate Br-HCA and morpholine to the organic solvent and mix evenly, the molar ratio of the intermediate Br-HCA, morpholine and the organic solvent is 1:2~10:60~1000, ...

Embodiment 1

[0038] A preparation method of a lysosome fluorescent probe based on a chalcone molecule, comprising the steps of:

[0039] The preparation of step (1) intermediate Br-HCA

[0040] 2'-Hydroxychalcone (HCA, 0.668g, 2.5mmol) and 1,3-dibromopropane (1.010g, 5mmol) were dissolved in 15mL of N,N-dimethylformamide, and anhydrous potassium carbonate was added (0.518 g, 3.75 mmol). The temperature was raised to 80°C and the reaction was refluxed for 8h. The reaction was stopped, and then extracted with ethyl acetate. After extraction, the organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and distilled under reduced pressure. The crude product was separated by silica gel column chromatography to obtain the compound Br-HCA with a yield of 51%.

[0041] Step (2) Preparation of Lysosome Fluorescent Probe Lyso-HCA

[0042] Compound Br-HCA (39mg, 0.1mmol) and morpholine (43mg, 0.5mmol) were added in a 100mL round bottom flask, and then 5mL of acetonitrile wa...

Embodiment 2

[0044] A preparation method of a lysosome fluorescent probe based on a chalcone molecule, comprising the steps of:

[0045] The preparation of step (1) intermediate Br-HCA

[0046] 2'-Hydroxychalcone HCA (0.267g, 1mmol) and 1,3-dibromopropane (1.010g, 5mmol) were dissolved in 8mL of N,N-dimethylformamide, cesium carbonate (0.652g, 2 mmol). The temperature was raised to 80°C and the reaction was refluxed for 12h. The reaction was stopped, and then extracted with ethyl acetate. After extraction, the organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and distilled under reduced pressure. The crude product was separated by silica gel column chromatography to obtain the compound Br-HCA with a yield of 58%.

[0047] Step (2) Preparation of Lysosome Fluorescent Probe Lyso-HCA

[0048] Compound Br-HCA (78mg, 0.2mmol) and morpholine (70mg, 0.8mmol) were added to a 100mL round bottom flask, then 5mL of acetonitrile was added, cesium carbonate (130mg, 0.4mmo...

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Abstract

The invention discloses a lysosome fluorescent probe of chalcone as well as a preparation method and application of the lysosome fluorescent probe, and belongs to the technical field of organic molecular fluorescent probes. The preparation method comprises the following steps: adding 2 '-hydroxychalcone HCA and 1, 3-dibromopropane into an organic solvent for reaction, carrying out silica gel column chromatography separation to obtain an intermediate Br-HCA, adding the intermediate Br-HCA and morpholine into the organic solvent for reaction, and carrying out silica gel column chromatography separation to obtain the lysosome fluorescent probe Lyso-HCA. The preparation method of the fluorescent probe is simple, rapid and low in cost, the prepared fluorescent probe is low in background interference, high in detection sensitivity and high in excitation capacity when being applied to cell fluorescence imaging, and the fluorescent probe is good in stability to an acid-base environment and good in specificity to lysosome fluorescence imaging. The probe provides a tool with a wide application prospect for cell lysosome fluorescence imaging research.

Description

technical field [0001] The invention belongs to the technical field of organic molecular fluorescent probes, and relates to a chalcone-based lysosome fluorescent probe and a preparation method and application thereof. Background technique [0002] Lysosome is an important organelle in eukaryotic cells. It contains a variety of acid hydrolases. It is the main place for cells to decompose various exogenous and endogenous macromolecules. It also participates in cell autophagy, differentiation and apoptosis. In addition, it is also closely related to the occurrence of various genetic diseases and tumors. Therefore, it is of great significance to monitor the changes of lysosomes in living cells. Fluorescence imaging is a powerful tool for studying the morphology, distribution and dynamic changes of lysosomes in cells. It has many advantages such as good specificity, real-time, and visualization. Some commercial organic molecular fluorescent probes have been widely used in targe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/088C09K11/06G01N21/64
CPCC07D295/088C09K11/06G01N21/6402G01N21/6428G01N21/6458C09K2211/1033C09K2211/1007G01N2021/6439
Inventor 王超冯梦祥代方方赵敏王晨
Owner SHAANXI UNIV OF SCI & TECH
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