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Rhodol-HBT derivative and preparation method and application thereof

A technology of derivatives and reactions, applied in the field of chemical biology sensors, can solve the problems of invasion effect, different positioning and metabolism of probes, crosstalk of fluorescent signals, etc., and achieve high sensitivity, enhanced sensitivity, and good photostability

Active Publication Date: 2020-09-08
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, a series of specific small molecule fluorescent probes have been used to identify and detect thiophenol or hypochlorous acid in organisms, although simply mixing two specific probes together may be based on two different Signal discrimination detects two analytes, but this strategy is limited by various issues, such as: (1) the possibility of crosstalk between the fluorescent signals of two probes; (2) the possibility of crosstalk between the fluorescent signals of the two probes; The introduction of two kinds of probes may lead to the invasion effect of this strategy; (3) The two probes may have different localization and metabolism
Therefore, the development of a single-molecule dual-mode fluorescent probe for the visualization of thiophenol-induced oxidative stress processes and the dynamic assessment of senescence is highly desirable, but at the same time very challenging.

Method used

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  • Rhodol-HBT derivative and preparation method and application thereof
  • Rhodol-HBT derivative and preparation method and application thereof
  • Rhodol-HBT derivative and preparation method and application thereof

Examples

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Embodiment 1

[0042] Example 1 Preparation and application of fluorescent probe ROSH

[0043]

[0044] (1) Accurately weigh 2.18 g (20 mmol) of the compound m-aminophenol and 4.24 g (40 mmol) of anhydrous sodium carbonate and accurately measure 10 mL (100 mmol) of 1-bromo-3-chloropropane in a 50 mL round bottom In the flask, 15 mL of N,N-dimethylformamide was added thereto, heated to 80 °C and stirred for 15 h under the protection of argon, the color of the system changed from light yellow to dark green. After the reaction, the reaction system cooled to room temperature was poured into an appropriate amount of distilled water, and the reagent dichloromethane was used to extract the system several times, the organic phase was recovered and dried by adding anhydrous sodium sulfate for 0.5 h, and the solvent was removed after filtration to obtain a crude product. The compound was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate: 15 / 1, V / V), and finally obt...

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Abstract

The invention discloses a Rhodol derivative as shown in a structural general formula (I). According to the invention, benzothiazole is introduced into a Rhodol structure, a novel Rhodol-HBT dye is developed, the dye has multiple excellent properties of two fluorophores Rhodol and HBT, and two active sites which are easy to modify are provided. The compound can be used as a fluorescent probe for logic detection of thiophenol and hypochlorous acid, visual imaging of the oxidative stress process in cells, zebra fishes and nematodes is successfully achieved by means of a fluorescence confocal microscope, and dynamic evaluation of aging of the cells and the nematodes is further achieved by means of the probe.

Description

technical field [0001] The invention relates to Rhodol-HBT derivatives and a preparation method and application thereof, belonging to the technical field of chemical biological sensors. Background technique [0002] Aging is a time-dependent decline in physiological function that affects most organisms and is the most serious risk factor for many non-communicable diseases, including osteoarthritis, atherosclerosis, Alzheimer's disease, and cancer. Therefore, the detection and evaluation of aging is helpful to the research on the mechanism of aging and aging-related diseases. In 1956, Dr. Harman first proposed the free radical theory, which believed that free radical-induced cell damage is the cause of aging. Subsequently, the free radical hypothesis was fused with the oxidative stress hypothesis, and it was proposed that oxidative stress damage is the cause of aging, and that the level of reactive oxygen species (ROS) in the resting state is closely related to the degree of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/22C09K11/06G01N21/64A61K49/00
CPCC07D491/22C09K11/06G01N21/6428G01N21/643G01N21/6458A61K49/0021G01N2021/6497C09K2211/1048C09K2211/1037
Inventor 郭媛天敬业滕浩修梦雪
Owner NORTHWEST UNIV
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