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Fluorescent probes based on quinoxalinone aryl sulfides and their preparation methods and applications

A quinoxalinone and reaction technology, applied in the field of medical diagnosis, can solve the problems of low selectivity and slow catalytic rate, and achieve the effect of simple chemical structure, high selectivity and easy preparation

Active Publication Date: 2020-07-14
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the traditional chemical small molecule catalysts reported by the Simonneaux research group have low selectivity and slow catalytic rates.

Method used

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  • Fluorescent probes based on quinoxalinone aryl sulfides and their preparation methods and applications
  • Fluorescent probes based on quinoxalinone aryl sulfides and their preparation methods and applications
  • Fluorescent probes based on quinoxalinone aryl sulfides and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] This embodiment relates to a kind of quinoxalinone derivative, and its preparation method is as follows:

[0055] (1) 4-Methoxy o-phenylenediamine (0.1mol, 13.8g) was dispersed in absolute ethanol (150mL), ethyl pyruvate (0.12mol, 13.92g) was added dropwise under ice-cooling, stirred at room temperature for 12h, The reaction solution was filtered, the filter cake was washed with absolute ethanol, and dried to obtain white powder 1a (13.6 g, yield 86%).

[0056] (2) 1a (20mmol, 3.2g), K 2 CO 3 (24mmol, 3.31g) was dispersed in acetone, and then methyl bromoacetate (24mmol, 3.67g) was added dropwise under stirring. The reaction mixture was reacted overnight at 62°C, the solvent was evaporated, and the residue was added to water and ethyl acetate, The ethyl acetate phase was separated, separated on a silica gel column (petroleum ether: ethyl acetate = 10:1), and purified to obtain 3.0 g of 1b with a yield of 54%.

[0057] (3) Suspend 1b (2mmol, 500mg) in acetic acid, add...

Embodiment 2

[0064] Configure 1mg / mL QS-4 DMSO stock solution, and then pass through different ratios of DMSO / H 2 The mixed solvent of O dilutes QS-4 into a solution with a concentration of 10 μg / mL. The absorption spectrum of QS-4 is measured by a Thermo Electron-EV300 UV-Vis spectrophotometer, and then the QS-4 is measured by a steady-state time-resolved fluorescence spectrophotometer Fluorescence spectra and their fluorescence quantum yields were measured. The test results found that with the increase of the water ratio, the fluorescence emission wavelength and its fluorescence intensity gradually increased. In the aggregated state, the maximum emission wavelength of QS-4 reached 595nm. This result shows that QS-4 has the effect of aggregation-induced fluorescence enhancement (AIE) . The absolute fluorescence quantum yield of QS-4 measured in the aggregated state is 2.2%.

Embodiment 3

[0066] Prepare a DMSO stock solution containing 1 mg / mL QS-4 and store it at room temperature in the dark. Human cervical cancer HeLa cells were planted in culture dishes at a density of 10 5 / mL, after they adhered to the wall, Erastin was added to continue culturing for 24 hours, and the cells in the control group were not treated. Then add the probe QS-4, continue to incubate for 30min, observe the change of QS-4 by laser confocal microscope. The results showed that after ferroptosis was induced in HeLa cells, the cells emitted a very obvious green light, while the cells without erastin treatment emitted red fluorescence. figure 1 Schematic diagram of the reaction of probe QS-4 detecting ferroptosis, which changes from red fluorescence to green fluorescence. Figure 4 It is the laser confocal imaging diagram of cervical cancer cells under different conditions in Example 3, wherein, in Figure a, the first line is the fluorescence imaging of cervical cancer cells under norm...

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Abstract

The invention provides a fluorescent probe based on quinoxalinone aryl sulfides as well as a preparation method and application thereof. A chemical structure of a fluorescent probe molecule is shown in formula (I) (shown in the specification), wherein R is selected from allyl and derivatives thereof, benzyl and derivatives thereof, fatty acid ester groups with the carbon atom number of 1-8 or fatty acid with the carbon atom number of 1-8; R1 is selected from alkoxy with the carbon atom number of 1-8, halogen or alkyl with the carbon atom number of 1-8; and R2 is aryl sulfides. The fluorescentprobe molecule is obtained by cyclizing o-phenylenediamine and derivatives thereof, carrying out nucleophilic substitution and carrying out aldol condensation reaction. The quinoxalinone derivative compound turns red fluorescence into green fluorescene after thioether is oxidized into sulfoxide in the presence of up-regulated heme oxidase and active oxygen in ferroptosis cells. The fluorescent probe provided by the invention can be directly added into a culture medium, then acts on cells and carries out detection, and also can be directly injected intravenously or intratumorally and play a role of animal in vivo detection.

Description

technical field [0001] The invention relates to the field of medical diagnosis, in particular to a fluorescent probe based on quinoxalinone aryl sulfides and its preparation method and application. Background technique [0002] Ferroptosis is a new cell death method discovered for the first time in 2012. Different from the traditional cell apoptosis method, ferroptosis is an apoptosis mediated by iron that does not depend on the participation of caspases proteases. In the process of ferroptosis, a large amount of active oxygen, oxidase, and severely down-regulated reduced glutathione will accumulate in the cell. [0003] Although many molecular biological mechanisms of ferroptosis remain to be further studied, current studies have shown that the occurrence of ferroptosis is closely related to many diseases, such as malignant tumors, neurodegenerative diseases Parkinson's disease, Alzheimer's disease, etc. Therefore, the design and development of specific ferroptosis detecti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/06C07D417/06C07D405/06C07D403/06C07D241/44C09K11/06G01N21/64
CPCC07D241/44C07D403/06C07D405/06C07D409/06C07D417/06C09K11/06C09K2211/1007C09K2211/1029C09K2211/1037C09K2211/1044C09K2211/1088C09K2211/1092G01N21/6428G01N2021/6439
Inventor 金鑫施雷雷朱新远童刚生
Owner SHANGHAI JIAO TONG UNIV
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