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Aggregation-inducing luminescent lysosomal probe independent of acidic pH, preparation method thereof and application thereof

A technology of aggregation-induced luminescence and lysosomes, which is applied in the field of aggregation-induced luminescence lysosome probes and its preparation, can solve the problems of low luminescence efficiency in the aggregated state of materials, complex biosynthesis methods, and high raw material costs, and achieve the goal of being free from micro-organisms. Effect of environmental acidity, good light stability, and low raw material cost

Active Publication Date: 2019-03-05
THE HONG KONG UNIV OF SCI & TECH
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Problems solved by technology

[0003] The technical problem to be solved by the present invention is that the biological probes in the prior art are usually pH-dependent, and the luminescence is changed by the acidity of the microenvironment, which has the technical problem of instability, and solves the complex biosynthesis method and high cost of raw materials in the prior art , The technical problem of the low luminous efficiency of the aggregated state of the synthesized material

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  • Aggregation-inducing luminescent lysosomal probe independent of acidic pH, preparation method thereof and application thereof
  • Aggregation-inducing luminescent lysosomal probe independent of acidic pH, preparation method thereof and application thereof
  • Aggregation-inducing luminescent lysosomal probe independent of acidic pH, preparation method thereof and application thereof

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preparation example Construction

[0047] The preparation method of the aggregation-induced luminescent lysosome probe independent of acidic pH specifically comprises the following steps: performing Buchwald-Hartwig coupling on the halogen-substituted phenylvinyl derivative A and the heterocyclic derivative B The reaction generates a crude product, the solvent in the crude product is removed, ethanol and acetone are added to dissolve the crude product, filtered, the filtrate is dried, and then purified by silica gel column chromatography using chloroform and methanol as eluents to obtain Aggregation-induced luminescent lysosome probe, wherein the chemical structural formula of the halogen-substituted phenylvinyl derivative A is

[0048] Wherein X' is a halogen, and X' is a bromo group; the chemical structural formula of the heterocyclic derivative B is: N-methylpiperazine or morpholine

[0049] Taking X' in phenylethylene derivatives A as bromine (Br), heterocyclic derivatives B as , the general chemica...

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Abstract

The invention provides an aggregation-inducing luminescent lysosomal probe independent of acidic pH, a preparation method and an application thereof. The preparation method comprises the steps of: halogen-substituted phenylvinyl derivative A and heterocyclic derivative B to Buchwald - Hartwig coupling reaction to form the crude product, remove the solvent in the crude product, add ethanol and acetone to dissolve the crude product, filter, the filtrate is dried, and then purified by silica gel column chromatography with chloroform and methanol as eluent, ie An aggregation-inducing luminescent lysosomal probe that does not depend on acidic pH is obtained. The bioprobe of the present invention has a property that does not depend on an acidic pH change, and is responsive to environmental viscosity. Its mechanism of action in lysosome imaging is viscosity-induced intramolecular motion limitation, which has better photostability and is not affected by microenvironmental acidity than traditional PET mechanism of action.

Description

technical field [0001] The invention belongs to the technical field of biological imaging, and in particular relates to an aggregation-induced luminescent lysosome probe independent of acidic pH, a preparation method and application thereof. Background technique [0002] Lysosome is an important class of organelles involved in various cellular metabolic processes such as cell digestion, and its dysfunction is related to various diseases. Since its lumen has always maintained an acidic environment (pH = 3.8-6.6), most biological probes used to target lysosomes are usually pH-dependent, and their mechanism of action mainly relies on photo-induced electron transfer inhibited by protonation (PET). However, the lysosomal probe with this working mechanism has a low signal-to-noise ratio, and its luminescence is changed by changes in the acidity of the microenvironment, which is unstable. Therefore, the development of lysosome-targeting probes that do not depend on acidic pH is o...

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Application Information

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IPC IPC(8): C07D295/033C07D295/155C09K11/06G01N21/64
CPCG01N21/643C09K11/06C07D295/033C07D295/155C09K2211/1033C09K2211/1044C09K2211/1007G01N2021/6432
Inventor 唐本忠蔡元婧
Owner THE HONG KONG UNIV OF SCI & TECH
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