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A kind of benzothiazole 2-acetonitrile derivative and its application

A technology of benzothiazole and its derivatives, which is applied in the application field of benzothiazole 2-acetonitrile, can solve the problems of easy quenching and no aggregation-induced luminescent effect, and achieve good biocompatibility

Inactive Publication Date: 2018-06-05
SOUTHERN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, benzothiazole fluorescent dyes are easily quenched in solution and do not have the aggregation-induced luminescent effect

Method used

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  • A kind of benzothiazole 2-acetonitrile derivative and its application
  • A kind of benzothiazole 2-acetonitrile derivative and its application
  • A kind of benzothiazole 2-acetonitrile derivative and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 1. Preparation of benzothiazole 2-acetonitrile derivatives

[0021] Add 1.77g (10mmol) 4-(diphenylamine) benzaldehyde, 1.74g (10mmol) benzothiazole 2-acetonitrile-2-acetonitrile and 0.77g (10mmol) ammonium acetate in a 50mL flask, and then add 20mL of absolute ethanol. After reacting overnight at room temperature, the precipitate was filtered and recrystallized in ethanol to obtain 2.36 g of an orange-yellow solid. Yield 71%.

[0022] 2. Compound Characterization

[0023] 1 H NMR (400MHz, CDCl 3 )δ (ppm): 7.98 (s, 1H), 7.92 (d, 1H), 7.87 (d, 2H), 7.77 (d, 1H), 7.39 (t, 1H), 7.27 (t, 1H), 6.61 ( d, 2H), 3.36(dd, 4H), 1.64(s, IH), 1.14(t, 6H).

[0024] 13 C NMR (100MHz, CDCl 3 )δ (ppm): 163.88, 152.83, 149.82, 145.86, 132.42, 125.49, 123.96, 121.73, 120.42, 118.58, 110.28, 95.88, 43.68, 28.68, 11.57.

[0025] IR (v-1, KBr): 3396, 2973, 2357, 2208, 1590, 1569, 1515, 1468, 1405, 1352, 1268, 1179, 1146, 1069, 986, 819, 762, 724, 670, 584, 519 .

[0026] HR-MS(ESI):...

Embodiment 2

[0029] Embodiment 2 (fluorescent properties of benzothiazole 2-acetonitrile derivatives)

[0030] Prepare acetonitrile solution of benzothiazole 2-acetonitrile derivative with a concentration of 5mM, take 10 μL of benzothiazole 2-acetonitrile derivative acetonitrile solution, add it to a 10mL volumetric flask, add 1, 2, 3, 4, 5, 6, 7 , 8, 9mL of distilled water, and then add acetonitrile to adjust the volume of the solution to 10mL to obtain a water / acetonitrile solution (9 / 1, v / v) of benzothiazole 2-acetonitrile derivatives with a concentration of 5 μM, and a benzothiazole with a concentration of 5 μM 2-acetonitrile derivative water / acetonitrile solution (8 / 2, v / v), the concentration of benzothiazole 2-acetonitrile derivative water / acetonitrile solution (7 / 3, v / v), the concentration of 1 μM benzene Benzothiazole 2-acetonitrile derivative water / acetonitrile solution (6 / 4, v / v), the concentration is 5 μM Benzothiazole 2-acetonitrile derivative water / acetonitrile solution (5 / 5, ...

Embodiment 3

[0039] Embodiment 3 (cell culture and fluorescence imaging)

[0040] HeLa cells in the logarithmic growth phase were inoculated into a 6-well plate, cultured overnight, replaced with 1640 culture medium containing 10 μM of the benzothiazole 2-acetonitrile derivative obtained in Example 1, and continued to culture for 30 minutes, then phosphate buffered saline The 6-well plate was washed three times with liquid to remove excess benzothiazole 2-acetonitrile derivative. After the cells were continued to be cultured in 1640 culture medium with DAPI (10 g / ml) for 30 min, the 6-well plate was washed 3 times with phosphate buffered saline to remove excess DAPI. Cells were observed under a confocal laser microscope. Shows yellow-green fluorescence in the cytoplasm.

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Abstract

The invention relates to a benzothiazole 2-acetonitrile derivative. The chemical structure of the benzothiazole 2-acetonitrile derivative is as shown in the following formula (I). The benzothiazole 2-acetonitrile derivative is obtained by reaction of 4-(diethanol amine) benzaldehyde and benzothiazole 2-acetonitrile. The benzothiazole 2-acetonitrile derivative can perform fluorescence labeling on intracellular mitochondria.

Description

technical field [0001] The invention belongs to the field of organic chemistry, relates to a benzothiazole 2-acetonitrile compound, and also relates to the application of the benzothiazole 2-acetonitrile. Background technique [0002] Mitochondria are the site of oxidative metabolism in eukaryotes, where carbohydrates, fats and amino acids are finally oxidized to release energy. Mitochondria can provide a place for the life activities of cells and is the main place for intracellular oxidative phosphorylation and ATP formation. In addition, mitochondria have their own DNA and genetic system, but the number of genes in the mitochondrial genome is limited, so mitochondria are only a semi-autonomous organelle. In addition to providing energy for cells, mitochondria are also involved in processes such as cell differentiation, cell information transmission and apoptosis, and have the ability to regulate cell growth and cell cycle. Therefore, it is of great scientific significanc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/64C09K11/06G01N21/64
CPCC07D277/64C09K11/06C09K2211/1037G01N21/6486
Inventor 刘瑞源严轶琛路新卫游文伟
Owner SOUTHERN MEDICAL UNIVERSITY
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