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Fluorescent dye emitting near-infrared light and preparation method thereof

A technology of fluorescent dyes and near-infrared light, applied in the field of fluorescent dyes emitting near-infrared light and preparation thereof, can solve the problems of short excitation wavelength, interference, difficult tissue penetration depth, etc., and achieves strong practicability, simple preparation process, low cost effect

Active Publication Date: 2020-11-03
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the most widely used fluorescent dyes are derivatives of fluorescein, coumarin, rhodamine, and naphthalimide. Although they have abundant sources and thorough research on their properties, they generally have a shortcoming, that is, the maximum absorption wavelength and the maximum emission wavelength are not long enough, so that when it is applied to the imaging of living cells, tissues or living bodies, the excitation wavelength is relatively short, and it is difficult to have a deep tissue penetration depth. The interference of fluorescence, combined makes it difficult for dyes to exert the optimal effect of fluorescence technology

Method used

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  • Fluorescent dye emitting near-infrared light and preparation method thereof
  • Fluorescent dye emitting near-infrared light and preparation method thereof
  • Fluorescent dye emitting near-infrared light and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0029] A fluorescent dye that emits near-infrared light, composed of figure 1 The reaction scheme shown in the preparation. Its preparation steps are as follows:

[0030] (1) Under argon protection, reactant 1 (0.20 g, 1.03 mmol) and reactant 2 (0.26 g, 1.03 mmol) were mixed in a Schlenk tube, and sodium acetate (4.1 mg, 0.05 mmol) was added as a catalyst, Then 3 mL of tetrahydrofuran was added as a reaction solvent, and stirred at 20 °C for 24 h.

[0031] (2) After the solvent was removed by rotary evaporation, it was purified by silica gel column chromatography, and the eluent was dichloromethane / ethyl acetate (18 / 1, v / v). A fluorescent dye emitting near-infrared light (0.32 g) was obtained with a yield of 73%.

[0032] The obtained mass spectrum of the fluorescent dye is as follows figure 2 shown.

[0033] Obtain the ultraviolet-visible absorption spectrum figure and fluorescence spectrum figure of fluorescent dye in phosphate buffered saline solution as image 3 and...

Embodiment 2

[0038] A fluorescent dye emitting near-infrared light, the preparation steps of which are as follows:

[0039] Under argon protection, reactant 1 (0.20 g, 1.03 mmol) and reactant 2 (0.30 g, 1.20 mmol) were mixed in a Schlenk tube, and ammonium acetate (38.5 mg, 0.50 mmol) was added as a catalyst, and then 3 mL tetrahydrofuran and 1 mL ethanol were used as reaction solvents, and stirred at 30 °C for 12 h.

[0040] After the solvent was removed by rotary evaporation, it was purified by silica gel column chromatography, and the eluent was dichloromethane / ethyl acetate (18 / 1, v / v). A fluorescent dye emitting near-infrared light (0.38 g) was obtained with a yield of 85%.

Embodiment 3

[0042] A fluorescent dye emitting near-infrared light, the preparation steps of which are as follows:

[0043] Under argon protection, reactant 1 (0.20 g, 1.03 mmol) and reactant 2 (0.20 g, 0.80 mmol) were mixed in a Schlenk tube, and triethylamine (0.10 g, 1.03 mmol) was added as a catalyst, and then added 3 mL of chloroform and 1 mL of acetonitrile were used as reaction solvents, and stirred at 50 °C for 2 h.

[0044] After the solvent was removed by rotary evaporation, it was purified by silica gel column chromatography, and the eluent was dichloromethane / ethyl acetate (18 / 1, v / v). 0.27 g of a fluorescent dye emitting near-infrared light was obtained, with a yield of 62%.

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Abstract

The invention relates to the technical field of fluorescence-based optical imaging, in particular to a fluorescent dye emitting near-infrared light and a preparation method thereof. The fluorescent dye is composed of a strong donor "diethylamino" and a strong acceptor "trifluoromethyl" and "malononitrile". The intramolecular charge transfer is very strong, so that the maximum absorption wavelength and the maximum The emission wavelengths all reach above 600nm. A test in a phosphate buffer solution found that its maximum absorption wavelength is 602nm, and its maximum emission wavelength is 667nm, reaching the range of near-infrared light. Its outstanding large excitation wavelength and emission wavelength make the dye, when used as a staining agent for cell or tissue imaging, effectively reduce background signal interference of organisms, increase signal penetration depth, and improve imaging quality. At the same time, because there is still an active hydroxyl group in the molecule, the dye can also be used as a precursor compound to construct a series of fluorescent probes for detecting active components in cells.

Description

technical field [0001] The invention relates to the technical field of fluorescence-based optical imaging, in particular to a fluorescent dye emitting near-infrared light and a preparation method thereof. Background technique [0002] Fluorescence technology has been widely studied and applied in the field of life analysis due to its advantages of simple operation, high sensitivity, visualization and non-destructive testing. Fluorescent dyes have played a huge role in cell imaging, detection of reactive oxygen species and reactive nitrogen species, and visual diagnosis and treatment of tumor cells. The most widely used fluorescent dyes are derivatives of fluorescein, coumarin, rhodamine, and naphthalimide. Although they have abundant sources and thorough research on their properties, they generally have a shortcoming, that is, the maximum absorption wavelength and the maximum emission wavelength are not long enough, so that when it is applied to the imaging of living cells,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/68C09B23/14C09K11/06G01N21/64
CPCC09B23/145C09K11/06C09K2211/1007C09K2211/1088G01N21/6428
Inventor 陈杜刚罗子娟陈莉党耶城
Owner WUHAN INSTITUTE OF TECHNOLOGY
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