Benzothiazole derivative and synthesis method and application thereof

A technology of benzothiazole and synthesis method, which is applied in the field of benzothiazole derivatives, can solve problems such as failure to achieve subcellular organelle localization, and achieve the effects of high sensitivity, good selectivity and low cost

Inactive Publication Date: 2020-05-29
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, although most fluorescent probes have good water solubility and near-infrared emission properties, they are limited to the detection of hypochlorous acid at the cellular level and fail to achieve subcellular organelle localization.

Method used

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  • Benzothiazole derivative and synthesis method and application thereof
  • Benzothiazole derivative and synthesis method and application thereof
  • Benzothiazole derivative and synthesis method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0038] Preparation and characterization of embodiment 1NSSN

[0039] 2-Aminothiophenol (0.625g, 5mmol) and 5-methyl salicylaldehyde (0.681g, 5mmol) were mixed in 15mL dimethyl sulfoxide, silver nitrate (0.009g, 0.05mmol) was added, and the mixture After reacting at room temperature for 2 hours, dilute with dichloromethane, wash with brine, combine the organic phases, remove the solvent under reduced pressure, use petroleum ether and ethyl acetate at a volume ratio of 6:1 as the eluent, separate by silica gel column chromatography, and purify to obtain Pale yellow powdery solid (0.893g, yield: 74.07%). 1 H NMR (600MHz, Chloroform-d) δ8.01(d, J=8.1Hz, 1H), 7.93(d, J=7.9Hz, 1H), 7.56-7.48(m, 2H), 7.43(t, J= 7.5Hz, 1H), 7.21(d, J=8.3Hz, 1H), 7.04(d, J=8.4Hz, 1H), 2.37(s, 3H). 13 C NMR (150MHz, Chloroform-d) δ169.41, 155.79, 151.84, 133.79, 132.60, 128.72, 128.34, 126.67, 125.47, 122.12, 121.52, 117.68, 116.33, 20.51.

[0040]2-(Benzo[d]thiazol-2-yl)-4-methylphenol (0.455g, 1.8m...

Embodiment 2

[0044] Prepare a fluorescent probe stock solution of 2mM NSSN with dimethylsulfoxide (DMSO); mix 2mL of PBS / CH 3 Add CN (1:1, v / v, pH=7.4) solution and 10 μL fluorescent probe stock solution into a fluorescent cuvette, take hypochlorous acid solution, and gradually add it to the cuvette with a micro-sampler, While adding the sample, it was detected on the fluorescence spectrophotometer. With the addition of hypochlorous acid (0-30μM), the fluorescence intensity at 670nm gradually weakened, and the fluorescence intensity at 540nm gradually increased ( Figure 4a ), the fluorescence showed a ratiometric change. When hypochlorous acid (30-120μM) was added, the fluorescence intensity gradually increased from 540nm to 552nm and stabilized ( Figure 4b ), should be a "turn-on" type change.

Embodiment 3

[0046] Prepare 2mM NSSN fluorescent probe stock solution with dimethyl sulfoxide (DMSO); add 2mL of PBS / CH to the fluorescent cuvette 3 CN (1:1, v / v, pH=7.4) solution and 10 μL fluorescent probe stock solution, and then add 10 times the equivalent of other analytes and hypochlorous acid: NSSN, Cl － ,Br － , I － ,CH 3 COO － ,NO 2 － ,NO 3 － ,Cys,Hcy,GSH,S 2 o 3 2－ , SO 4 2－ , SO 3 2－ , HSO 3 － ,KMnO 4 , detected on a fluorescence spectrophotometer ( Figure 5 ). Hypochlorous acid makes the fluorescence intensity of the detection system increase significantly at 552nm, and other analytes basically do not cause changes in the fluorescence intensity of the detection system.

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Abstract

The invention provides a benzothiazole derivative and a synthesis method and application thereof. The Chinese name of the derivative is called as (E)-2-(3-(benzo[d]thiazole-2-yl)-2-hydroxy-5-methylstyryl)-3-methylbenzo[d]thiazole-3-iodide, and the structural formula of the derivative is shown in the specification. The English name of the compound is (E)-2-(3-(benzo[d]thiazol-2-yl)-2-hydroxy-5-methlyryl)-3-methlylbenzo[d]thiazol-3-iumiodide, and the structural formula of the compound is shown in the specification. The reagent is named as NSSN, and can realize dual-mode detection of hypochlorousacid. According to the detection method, in a buffer solution of PBS / CH3CN (1: 1, v / v, pH=7.4), the content of hypochlorous acid is detected through a fluorescence spectrophotometer ratio type and aturn-on type. The detection process is simple, sensitive and rapid, and the detection result is accurate.

Description

technical field [0001] The invention relates to a benzothiazole derivative, specifically to a benzothiazole derivative and a synthesis method thereof, and the application of the derivative as a detection reagent in detecting hypochlorous acid. Background technique [0002] Mitochondria are the organelles of aerobic respiration, and the normal metabolism of cells is accompanied by the continuous production and consumption of reactive oxygen species. Reactive oxygen species (ROS) play an important role in many pathophysiological processes. An imbalance between reactive oxygen species (ROS) and antioxidants can lead to oxidative stress to mitochondrial fragmentation to apoptosis. In recent years, hypochlorous acid (HClO) has received extensive attention as a reactive oxygen species. On the one hand, hypochlorous acid kills invading pathogens and bacteria from the immune system. On the other hand, a large number of data show that excessive hypochlorous acid concentration can ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/66C09K11/06G01N21/64A61K49/00
CPCC07D277/66C09K11/06G01N21/6428A61K49/0021C09K2211/1037C09K2211/1007
Inventor 黄永飞阴彩霞霍方俊
Owner SHANXI UNIV
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