Fluorescent dye for emitting near-infrared light, and preparation method thereof

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

Active Publication Date: 2019-09-03
WUHAN INSTITUTE OF TECHNOLOGY
View PDF3 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Fluorescent dye for emitting near-infrared light, and preparation method thereof
  • Fluorescent dye for emitting near-infrared light, and preparation method thereof
  • Fluorescent dye for emitting near-infrared light, and preparation method thereof

Examples

Experimental program
Comparison scheme
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%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to the technical field of fluorescence-based optical imaging, particularly to a fluorescent dye for emitting near-infrared light, and a preparation method thereof, wherein the fluorescent dye is formed by conjugating a strong donor diethylamino and strong acceptors trifluoromethyl and malononitrile, and has strong intramolecular charge transfer effect, such that the maximum absorption wavelength and the maximum emission wavelength of the fluorescent dye achieve more than 600 nm. According to the present invention, the test results in a phosphate buffer solution show thatthe maximum absorption wavelength is 602 nm, and the maximum emission wavelength is 667 nm, such that the fluorescent dye achieves the category of near-infrared light; based on the large excitation wavelength and the large emission wavelength, the fluorescent dye as the staining agent for cell or tissue imaging can effectively reduce the background signal interference of organisms, increase the signal penetration depth, and improve the imaging quality; and the molecule of the fluorescent dye retains an active hydroxyl group, such that the dye can be used as the precursor compound to constructa series of fluorescent probes for detecting intracellular active components.

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C09B23/14C09K11/06G01N21/64
CPCC09B23/145C09K11/06C09K2211/1007C09K2211/1088G01N21/6428
Inventor 陈杜刚罗子娟陈莉党耶城
Owner WUHAN INSTITUTE OF TECHNOLOGY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap