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Tetraphenylethylene-based subcellular organelle viscosity probe, and preparation method and application thereof

A tetraphenylethylene and subcellular technology, applied in chemical instruments and methods, instruments, scientific instruments, etc., can solve the problems of insufficient water solubility of probes and low imaging contrast, and achieve good targeting specificity and strong anti-interference , Good water solubility effect

Active Publication Date: 2018-09-11
HUNAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of this, the present invention aims to propose a tetraphenylethylene-based subcellular organelle viscosity probe and its preparation method and application to solve the problems of insufficient water solubility of the probe and low imaging contrast of viscosity monitoring.

Method used

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  • Tetraphenylethylene-based subcellular organelle viscosity probe, and preparation method and application thereof
  • Tetraphenylethylene-based subcellular organelle viscosity probe, and preparation method and application thereof
  • Tetraphenylethylene-based subcellular organelle viscosity probe, and preparation method and application thereof

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Embodiment 1

[0065] Tetraphenylethylene-based subcellular organelle viscosity probes, the subcellular organelle viscosity probes include mitochondrial viscosity probes and lysosome viscosity probes, wherein the structural formula of the mitochondrial viscosity probes is as follows:

[0066]

[0067] Wherein the structural formula of the lysosome viscosity probe is as follows:

[0068]

[0069] For the synthetic route of the viscosity probe, see figure 2 .

[0070] 1, the synthesis of (4-bromophenyl) (4-methoxyphenyl) ketone

[0071] Dissolve 2.52g of 4-bromobenzoyl chloride and 6mL of anisole in 20mL of dichloromethane, and stir for 25min under ice-cooling. Then add 1.57g of aluminum chloride to the reaction solution, stir at room temperature for 13h, then pour ice water into the mixture, extract with water three times, filter, and distill under reduced pressure. The crude product is separated by column chromatography to obtain compound (4-bromo Phenyl)(4-methoxyphenyl)methanone,...

Embodiment 2

[0099] The preparation method of the subcellular organelle viscosity probe comprises the following steps:

[0100] 1, the synthesis of (4-bromophenyl) (4-methoxyphenyl) ketone

[0101] Dissolve 2.80g of 4-bromobenzoyl chloride and 8mL of anisole in 20mL of dichloromethane, and stir for 40min under ice-cooling. Then add 2.0g aluminum chloride to the reaction solution, stir at room temperature for 9h, then pour ice water into the mixture, extract with water three times, filter, and distill under reduced pressure, the crude product is separated by column chromatography to obtain compound (4-bromo Phenyl)(4-methoxyphenyl)methanone, yield 50.2%. 1 H-NMR (400MHz, CDCl 3 )δ (ppm): 7.796 (d, J = 8.8Hz, 2H), 7.624 (s, 4H); 6.968 (d, J = 8.4, 2H); 3.891 (s, 3H) 13 C-NMR (100MHz, CDCl 3 ): 194.45, 163.44, 137.01, 132.49, 131.52, 131.31, 129.73, 126.86, 113.71, 55.56.

[0102] 2. Synthesis of compound TPE-Br

[0103] Dissolve 4.22g of (4-bromophenyl)(4-methoxyphenyl)methanone in 10m...

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Abstract

The invention provides a tetraphenylethylene-based subcellular organelle viscosity probe, and a preparation method and an application thereof. The subcellular organelle viscosity probe comprises a mitochondrial viscosity probe and a lysosomal viscosity probe. The preparation method mainly comprises the following steps (1) synthesis of a compound TPE-Br, (2) synthesis of a compound TPE-CHO, (3) synthesis of the mitochondrial viscosity probe, and (4) synthesis of the lysosomal viscosity probe. The synthesized viscosity probe can be used for detecting the viscosity of subcellular organelles. Thepreparation method of the tetraphenylethylene-based subcellular organelle viscosity probe is simple; the synthesized viscosity probe has good water solubility, and has no influences on the state of studied cells in the working concentration range; the viscosity probe has weak self-fluorescence background, so the imaging contrast of the subcellular organ viscosity monitoring is improved; and the viscosity probe is sensitive to the viscosity, has strong anti-interference, and has good targeting specificity to the subcellular organelles.

Description

technical field [0001] The invention belongs to the field of organic biology technology, and in particular relates to a tetraphenylethylene-based subcellular organelle viscosity probe, a preparation method and application thereof. Background technique [0002] Intracellular viscosity essentially controls all diffusion-mediated processes, including material transport, signal transduction, biomolecular interactions, diffusion of metabolites, and electron transport. Mitochondria and lysosomes are two important organelles in eukaryotic cells, characterized by specific viscosity, which in turn play an important role in functions such as ATP generation and degradation of biomolecules. Abnormal viscosity can reflect a dysfunctional state and is closely related to various diseases. Abnormal mitochondrial viscosity is recognized to be associated with neurodegenerative diseases, diabetes and cellular malignancies, while abnormal lysosomal viscosity is a hallmark of disease, inflammat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/12C07D213/30C09K11/06G01N21/64
CPCC07D209/12C07D213/30C09K11/06C09K2211/1007C09K2211/1029G01N21/6486
Inventor 蒋健晖汪凤林陈文韩军燕唐丽娟唐昊
Owner HUNAN UNIV
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