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Cysteine fluorescent probe and preparation method thereof

A fluorescent probe, cysteine ​​technology, applied in the field of chemical analysis, can solve the problems of small Stokes shift, strong background signal interference, poor probe effect, etc., to achieve strong selectivity, high sensitivity, and improved imaging. quality effect

Inactive Publication Date: 2019-04-02
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the fluorescent probes for cysteine ​​that have been reported so far have short emission wavelengths and strong background signal interference; a few probes emit red light or near-infrared light, but the Stokes shift is too small, and the self-absorption phenomenon is serious , so that the probe is less effective

Method used

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  • Cysteine fluorescent probe and preparation method thereof
  • Cysteine fluorescent probe and preparation method thereof
  • Cysteine fluorescent probe and preparation method thereof

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Effect test

Embodiment 1

[0027] See figure 1 . Under argon protection, reactant 1 (0.23 g, 1.02 mmol) and reactant 2 (0.20 g, 1.05 mmol) were mixed in a Schlenk tube, and ammonium acetate (0.005 g, 0.05 mmol) was added as a catalyst, and then 2 mL tetrahydrofuran and 0.5 mL ethanol were used as reaction solvents, and stirred at 20 °C for 24 h. After the solvent was removed by rotary evaporation, it was purified by silica gel column chromatography, and the eluent was dichloromethane / acetone (20 / 1, v / v). A cysteine ​​fluorescent probe was obtained, 0.29 g, with a yield of 75%. ESI-HRMS: [M+Na]+, [C25H15NO4Na]+, Calculated: 416.0899; Found: 416.0881.

Embodiment 2

[0029] Under argon protection, reactant 1 (0.15 g, 0.66 mmol) and reactant 2 (0.16 g, 0.853 mmol) were mixed in a Schlenk tube, and ammonium acetate (0.05 g, 0.65 mmol) was added as a catalyst, and then 2 mL Tetrahydrofuran and 0.5 mL methanol were used as reaction solvents, and stirred overnight at 60 °C. After the solvent was removed by rotary evaporation, it was purified by silica gel column chromatography, and the eluent was dichloromethane / acetone (20 / 1, v / v). 0.21 g of a cysteine ​​fluorescent probe was obtained with a yield of 78%. ESI-HRMS: [M+Na]+, [C25H15NO4Na]+, Calculated: 416.0899; Found: 416.0883.

Embodiment 3

[0031] Under argon protection, reactant 1 (0.34 g, 1.52 mmol) and reactant 2 (0.41 g, 1.45 mmol) were mixed in a Schlenk tube, and ammonium acetate (0.12 g, 1.61 mmol) was added as a catalyst, and then 2.5 mL Ethanol was used as the reaction solvent and stirred at 80°C for 3h. After the solvent was removed by rotary evaporation, it was purified by silica gel column chromatography, and the eluent was dichloromethane / acetone (20 / 1, v / v). 0.45 g of a cysteine ​​fluorescent probe was obtained with a yield of 78%. ESI-HRMS: [M+Na]+,[C25H15NO4Na]+, Calculated: 416.0899; Found: 416.0907.

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Abstract

The invention discloses a cysteine fluorescent probe and a preparation method thereof. According to the present invention, the fluorescent probe selectively reacts with cysteine, and the acryloyl group is broken, such that the fluorescence emission of the fluorescent group is restored so as to selectively detect the cysteine; due to the strong influence of the electron donor-receptor system on thefluorescent group, the intramolecular charge transfer effect is obvious, and the long-wavelength fluorescence emission and the large Stokes shift can be simultaneously obtained so as to effectively reduce the background interfering signals and improve the imaging quality; and the fluorescent probe has an emission wavelength of 636 nm and a Stokes shift of 158 nm, and has characteristics of high selectivity, high sensitivity and excellent imaging.

Description

technical field [0001] The invention relates to the technical field of chemical analysis, in particular to a cysteine ​​fluorescent probe and a preparation method thereof. Background technique [0002] There are three small molecule thiol amino acids widely present in cells, including cysteine, homocysteine ​​and glutathione, and they are involved in a large number of important biological processes. Among them, cysteine ​​plays a very important role in the process of protein synthesis, metabolism and detoxification, and is closely related to the occurrence of many diseases, such as growth retardation, edema, liver damage, cardiovascular disease and Alzheimer's disease illness etc. At the same time, these three thiol amino acids have similarities in structure, therefore, the selective detection of cysteine ​​in living cells is of great significance and is very challenging, and will be useful for the auxiliary diagnosis and treatment of some diseases. Prognosis provides valu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/68C09K11/06G01N21/64
CPCC07D307/68C09K11/06C09K2211/1007C09K2211/1011C09K2211/1088G01N21/6428
Inventor 陈杜刚陈莉党耶城余响林
Owner WUHAN INSTITUTE OF TECHNOLOGY
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