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Thiazole orange derivative, preparation and application thereof in mitochondria

A technology of orange derivatives and mitochondria, which is applied in the field of fluorescent probes, can solve the problems that have not been explored clearly, lack of detection methods, and the dynamic folding process of mitochondrial G-quadruplex is not clear, so as to achieve good nucleic acid discrimination effect

Active Publication Date: 2020-12-15
GUANGDONG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the lack of reliable detection methods, the relationship between mitochondrial G-quadruplex and life activities has not been explored clearly, and the dynamic folding process of mitochondrial G-quadruplex in vivo has not yet been clarified

Method used

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  • Thiazole orange derivative, preparation and application thereof in mitochondria
  • Thiazole orange derivative, preparation and application thereof in mitochondria
  • Thiazole orange derivative, preparation and application thereof in mitochondria

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preparation example Construction

[0064] see figure 2 , figure 2 The synthesis diagram of the preparation method of the thiazole orange derivative provided in the embodiment of the present application, the specific reaction steps of a thiazole orange derivative of the present invention are:

[0065] (1) Add the compound (2mmol) of the formula II structure or the compound (2mmol) of the formula III structure and 4-chloro-2-methylquinoline (2mmol) in 10ml of anhydrous acetonitrile solution, reflux at 100 ℃, react After 24 hours, cool to room temperature, dropwise add 20ml of diethyl ether for recrystallization, a purple-black solid precipitates, collect the solid, and purify to obtain a compound of the product formula VI structure;

[0066] (2) Mix the compound of formula IV structure (0.5mmol) with 2-methylbenzothiazole (1.5mmol), condense and reflux at 85°C, react for 6 hours, after cooling to room temperature, add 10ml of diethyl ether dropwise for recrystallization, and filter Collect the precipitate, th...

Embodiment 1

[0070] The application provides thiazole orange derivatives (I-a), and its synthetic method comprises:

[0071] (1) Add the compound of formula II structure (2mmol) and 4-chloro-2-methylquinoline (2mmol) into 10ml of anhydrous acetonitrile solution, condense and reflux at 100°C, react for 24 hours, cool to room temperature, drop 20ml of diethyl ether was recrystallized, and a purple-black solid was precipitated. The solid was collected and purified to obtain a compound of the product formula VI-a structure;

[0072]

[0073] The compound of formula VI-a structure 1 H NMR result is: 1 H NMR (DMSO, 400Hz): δ12.76(s, 1H), 8.23(m, 3H), 8.16(d, J=8.4Hz, 1H), 8.05–8.01(d, J=8.4Hz, 1H), 7.76–7.73(m,1H),5.07(m,2H),2.89(s,4H),2.80(s,3H); ESI-MS m / z 264.08[M-Br] + ;

[0074] (2) Mix the compound of formula IV structure (0.5mmol) with 2-methylbenzothiazole (1.5mmol), condense and reflux at 85°C, react for 6 hours, after cooling to room temperature, add 10ml of diethyl ether dropwi...

Embodiment 2

[0085] The application provides thiazole orange derivatives (I-b), and its synthetic method comprises:

[0086] (1) Add the compound of formula III structure (2mmol) and 4-chloro-2-methylquinoline (2mmol) into 10ml of anhydrous acetonitrile solution, reflux at 100°C, react for 24 hours, cool to room temperature, drop 20ml of diethyl ether was recrystallized, and a purple-black solid was precipitated. The solid was collected and purified to obtain a compound of the product formula VI-b structure;

[0087]

[0088] The compound of formula VI-b structure 1 H NMR result is: 1 H NMR (DMSO, 400Hz): δ8.59(d, J=7.9Hz, 1H), 8.42(d, J=7.9Hz, 1H), 8.25–8.04(m, 3H), 7.84(s, 2H), 5.57(s,2H),2.99(s,3H); ESI-MS m / z 235.06[M-Br] + ;

[0089] (2) Mix the compound of formula IV-a structure (0.5mmol) with 2-methylbenzothiazole (1.5mmol), condense and reflux at 85°C, react for 6 hours, after cooling to room temperature, add 10ml of diethyl ether dropwise for recrystallization , the precip...

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Abstract

The invention belongs to the technical field of fluorescent probes, and particularly relates to a thiazole orange derivative, preparation and application thereof in mitochondria. The invention provides a thiazole orange derivative in a first aspect. The thiazole orange derivative has a structure shown as formula I in the specification; wherein R1 is a fatty acid amide group of C1-6 and a fatty carboxyl group of C1-6; R2 is a fatty alkyl group of C1-6; the second aspect of the invention provides a preparation method of the thiazole orange derivative. The preparation method comprises the following steps of: reacting a compound with a structure shown as formula VIII with a compound with a structure shown as formula V to obtain the thiazole orange derivative, wherein n is an integer of 0-6; Xis methyl, I, Br or Cl; R5 is an amide group or a carboxyl group; and R4 is methylthio group. The invention provides a thiazole orange derivative for targeted detection of mitochondria and mitochondria G-quadruplex DNA. The thiazole orange derivative can specifically detect mitochondria and mitochondria G-quadruplex DNA.

Description

technical field [0001] The application belongs to the technical field of fluorescent probes, and in particular relates to a thiazole orange derivative, its preparation and application in mitochondria. Background technique [0002] Due to its high sensitivity, low cost, easy operation, no damage to body tissues, and the ability to achieve real-time tracer imaging, fluorescein contrast imaging technology has made a lot of progress in the detection and diagnosis of early cancers in recent years. [0003] Mitochondria are important organelles for cell survival, the energy factory of cells, and play a key role in the process of cell apoptosis. The abnormal activity of mitochondria in tumor cells is closely related to the infinite proliferation ability of tumors. Therefore, mitochondria have been considered as ideal targets for anti-tumor therapy, including material transport, interpretation of genetic information, regulation of gene expression, and some important biocatalysis. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06C09K11/06G01N21/64
CPCC07D417/06C09K11/06G01N21/6428C09K2211/1029C09K2211/1037C09K2211/1007
Inventor 龙威卢宇靖郑伯鑫佘梦婷黄玄贺陈翠翠张艺瀚钟冬晓张焜
Owner GUANGDONG UNIV OF TECH
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