Rhodol-hbt derivatives and their preparation methods and applications

A derivative and reaction technology, applied in the field of chemical biological sensors, can solve the problems of invasion effect, cross-talk of fluorescent signals, different positioning and metabolism of probes, etc.

Active Publication Date: 2022-06-07
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 derivatives and their preparation methods and applications
  • Rhodol-hbt derivatives and their preparation methods and applications
  • Rhodol-hbt derivatives and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

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 weigh 10 mL (100 mmol) of 1-bromo-3 chloropropane into a 50 mL round bottom 15 mL of N,N-dimethylformamide was added to the flask, and under argon protection, the reaction was heated to 80 °C and stirred for 15 h, and the color of the system changed from pale yellow to dark green. After the reaction was completed, the reaction system cooled to room temperature was poured into an appropriate amount of distilled water, the system was extracted several times with the reagent dichloromethane, the organic phase was recovered, and anhydrous sodium sulfate was added to dry for 0.5 h. After filtration, the solvent was removed to obtain a crude product. The compound was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate: 15 / 1, V / V...

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Abstract

The invention discloses Rhodol derivatives represented by general structural formula (I). The present invention introduces benzothiazole into the Rhodol structure, and develops a new type of Rhodol-HBT dye, which has multiple excellent properties of both Rhodol and HBT fluorophores, and provides two active sites that are easy to modify. The compound of the present invention can be used as a fluorescent probe for the logic detection of thiophenol and hypochlorous acid. With the help of fluorescent confocal microscopy, the visual imaging of the oxidative stress process in cells, zebrafish, and nematodes has been successfully realized. Using this probe A dynamic evaluation of senescence at the cellular and nematode level was also achieved.

Description

technical field [0001] The invention relates to Rhodol-HBT derivatives, a preparation method and application thereof, and belongs to the technical field of chemical biological sensors. Background technique [0002] Aging is a time-dependent physiological decline 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 for the research on the mechanism of aging and aging-related diseases. In 1956, Dr. Harman first proposed the free radical theory, which holds that free radical-induced cellular damage is the cause of aging. Subsequently, the free radical hypothesis was fused with the oxidative stress hypothesis, suggesting that oxidative stress damage is the cause of aging, and it is believed that the level of reactive oxygen species (ROS) in the resting state is closely related to the degree of agin...

Claims

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Application Information

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