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Indole-benzothiazole derivative as well as preparation method and application thereof

A technology for benzothiazole and derivatives, which is applied in the field of indole-benzothiazole derivatives and their preparation and application, can solve the problems of strong fluorescence response, small injection volume, and limited application of thiazole orange, and achieve high fluorescence intensity , strong specific effect

Active Publication Date: 2020-11-06
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] With the development of biotechnology, the previous method of sequencing DNA molecules through isotope effects can no longer meet the requirements; and fluorescent labeling is a labeling technology with the advantages of fast detection speed, good repeatability, small injection volume, and no radiation. Received extensive attention and achieved rapid development
Thiazole orange (TO) is a general-purpose nucleic acid dye. Its advantage is that it has a good staining effect on double-stranded DNA (ssDNA) and G-quadruplex DNA, and has a strong fluorescence response. The disadvantage is that it has poor specificity and cannot be specific. Sexually distinguishes ssDNA from G4-DNA, which limits the application of thiazole orange

Method used

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  • Indole-benzothiazole derivative as well as preparation method and application thereof
  • Indole-benzothiazole derivative as well as preparation method and application thereof
  • Indole-benzothiazole derivative as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0043] Embodiment 1: the synthesis of compound shown in formula (Ⅴ)

[0044] Weigh 1.0g (1.103mM) of 2-methylthiobenzothiazole (Ⅳ) and place it in an explosion-proof bottle, use 8mL of acetonitrile as a solvent, and ultrasonically vibrate to make the two evenly mixed; add twice the molar amount (2.206 mM) of methyl iodide, put the reaction system in an oil bath and turn on the magnetic stirring, the reaction temperature is 90°C, and the reaction time is 8h; after the reaction is completed, the reaction system is cooled to room temperature, and 10mL of ethyl acetate is added to fully shake , standing for 15min, the solid was precipitated, vacuum filtered, and the filter cake was rinsed with 5mL ethyl acetate, dried to obtain 1.07g white solid (Ⅴ), thin plate chromatography showed no by-products, and the crude yield was 60%. The reaction equation is as follows:

[0045]

Embodiment 2

[0046] Embodiment 2: the synthesis of compound shown in formula (IX)

[0047] Weigh 0.2g (0.956mM) of 1,1,2-trimethyl-1H-benzo[e]indole (Ⅷ) into an explosion-proof bottle, use 2mL of acetonitrile as a solvent, and ultrasonicate for 3min to mix the two evenly. Add twice the molar amount (1.912mM) of methyl iodide under the condition of the hood, place the reaction system in a pot and turn on the magnetic stirring, the reaction temperature is 90°C, and the reaction time is 8h; after the reaction is completed, the reaction system is cooled After reaching room temperature, add 5 mL of ethyl acetate to shake fully, let stand for 15 min, precipitate solid, vacuum filter, and wash the filter cake with 3 mL of ethyl acetate, dry to obtain 0.29 g of light yellow solid (IX), thin plate chromatography shows no by-products , the crude yield was 86%. The reaction equation is as follows:

[0048]

Embodiment 3

[0049] Embodiment 3: the synthesis of compound shown in formula (XI)

[0050] Weigh 0.2g (1.240mM) of 2,3,3-trimethyl-3H-indole (Ⅹ) into an explosion-proof bottle, use 2mL of acetonitrile as a solvent, and ultrasonically mix the two for 3min. Add twice the molar amount (2.48mM) of methyl iodide, place the reaction system in a pot and turn on magnetic stirring, the reaction temperature is 90°C, and the reaction time is 8h; after the reaction is completed, the reaction system is cooled to room temperature, and then added 5mL of ethyl acetate was fully shaken, left to stand for 15min, the solid was precipitated, vacuum filtered, and the filter cake was rinsed with 3mL of ethyl acetate, dried to obtain 0.26g of pink solid (Ⅺ), thin plate chromatography showed no by-products, the crude yield was 70%. The reaction equation is as follows:

[0051]

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Abstract

The invention provides an indole-benzothiazole derivative as well as a preparation method and application thereof. The indole-benzothiazole derivative is a compound shown as a formula (I). According to the indole-benzothiazole derivative as well as the preparation method and application thereof of the invention, the structure of an universal fluorescent probe thiazole orange is modified, so that the indole-benzothiazole derivative is obtained; the indole-benzothiazole derivative has a relatively large electronic conjugated system and a relatively large plane; the intramolecular charge transfereffect of the indole-benzothiazole derivative can influence the fluorescence emission intensity of molecules, and therefore, when the indole-benzothiazole derivative is used as a fluorescent probe, the indole-benzothiazole derivative can specifically recognize mitochondrial G-quadruplex DNA in an in-vitro experiment, and can dye the mitochondrial G-quadruplex DNA in cells in a cell experiment soas to achieve the purpose of detecting mitochondria and the mitochondrial G-quadruplex DNA. The indole-benzothiazole derivative provided by the invention has the advantages of high fluorescence intensity and strong specificity.

Description

technical field [0001] The invention specifically relates to an indole-benzothiazole derivative and its preparation method and application. Background technique [0002] Nucleic acid is not only the basic component of all biological cells, but also plays an important role in the growth, development, reproduction, inheritance and variation of organisms and other major life phenomena. Nucleic acid macromolecules are divided into two categories: deoxyribonucleic acid (DNA) and ribonucleic acid (RNA), which play a role in storing and transmitting genetic information in the replication and synthesis of proteins. G-quadruplex (G-quadruplex) is a special nucleic acid secondary structure that widely exists in guanine-rich regions in the human genome, including telomere ends of chromosomes, promoter regions, and mitochondrial DNA. Studies have shown that the formation of G-quadruplex has a regulatory effect on a series of physiological processes in vivo, such as signal transduction,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06C09K11/06G01N21/64
CPCC07D417/06C09K11/06G01N21/6428C09K2211/1029C09K2211/1037
Inventor 郑伯鑫卢宇靖龙威佘梦婷许泳渝陈翠翠
Owner GUANGDONG UNIV OF TECH
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