Unlock instant, AI-driven research and patent intelligence for your innovation.

Squaraine dye as well as preparation method and application thereof

A squaraine and dye technology, applied in organic dyes, chemical instruments and methods, methine-based/polymethine-based dyes, etc., can solve the problems of poor biological safety performance and slow metabolism of heavy metals, and achieve good fluorescence quantum yield, The effect of obvious reaction site and simple preparation method

Pending Publication Date: 2022-03-15
THE FOURTH AFFILIATED HOSPITAL OF ZHEJIANG UNIV SCHOOL OF MEDICINE
View PDF7 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, some inorganic materials such as rare earth down-conversion nanoparticles, carbon nanotubes, quantum dots, etc. can achieve emission in the second near-infrared region, but most of their emission wavelengths are located in the first region of the near-infrared, and heavy metals have poor biosafety performance. Disadvantages such as slow post-metabolism limit their application

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
  • Squaraine dye as well as preparation method and application thereof
  • Squaraine dye as well as preparation method and application thereof
  • Squaraine dye as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1, the synthesis of intermediate C

[0040]

[0041](1) Compound A (2.56g) was put into a round bottom flask containing 50ml DMF. After it was completely dissolved, sodium hydride (1.09g) was added in an ice-water bath. After stirring at room temperature for 5 minutes, n-butyl iodide was added. Alkane (4.27g), after stirring at room temperature for 2h, the reactant was washed with sodium chloride saturated water (2×50mL), then extracted with ethyl acetate and water (1:1 by volume), and the ethyl acetate layer After the solvent was removed by rotary evaporation, the crude product was obtained; the crude product was dissolved in 1 mL of ethyl acetate and used as a sample solution for silica gel column chromatography. Fill the chromatographic column (3cm×30cm) with 50g of 100-200mesh column chromatography silica gel and 50mL of ethyl acetate, release the ethyl acetate, slowly load the sample along the tube wall, and elute with ethyl acetate as the eluent. Th...

Embodiment 2

[0046] Embodiment 2, the synthesis of squaraine dye SQ890.

[0047]

[0048] Put the intermediate C (27mg) and squaraine (7mg) prepared by the method in Example 1 into a round-bottomed flask containing n-butanol (4ml) and toluene (4ml), heat and reflux at 110°C for 1h, and the reaction solution was rotary evaporated After removing the solvent, the concentrate was dissolved in 1 mL of dichloromethane and used as a sample solution for silica gel column chromatography. Fill a chromatographic column (3cm×30cm) with 50g of 100-200 mesh column chromatography silica gel and 50mL of dichloromethane, release the dichloromethane and slowly load the sample along the tube wall, and use dichloromethane as the eluent for elution. The off-rate is 1mL / min, the elution volume is 7 column volumes, the mixed solvent of dichloromethane and methanol (volume ratio is 10:1) is used as developing solvent for TLC monitoring, and the collected Rf value is 0.2-0.4 After the components of dichloromet...

Embodiment 3

[0052] Embodiment 3, squaraine dye absorption spectrum and emission spectrum detection

[0053] Ultraviolet-visible absorption spectrum test: adopt ultraviolet-visible light spectrophotometer (UV-5500PC, Shanghai Yuan Analysis Instrument Co., Ltd.) to carry out ultraviolet-visible absorption spectrum detection to the squarylium dye SQ890 prepared by the method of embodiment 2: take 300 μ L concentration to be 0.15mg / Place the SQ890 DMF solution of 1 ml in a quartz cuvette, set the DMF to zero as the baseline, and select the wavelength range of 650nm to 1100nm for spectral scanning. The results are shown in image 3 As shown, SQ890 has strong absorption between 750nm and 950nm.

[0054] Fluorescence emission spectrum test: adopt fluorescence spectrophotometer (PerkinElmer Lambda 750) to carry out fluorescence emission spectrum detection to squarylium dye SQ890 prepared by the method of embodiment 2: get 3ml concentration and be the SQ890DMF solution of 10 μ M, select 800nm~155...

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 discloses a squarylium cyanine dye and a preparation method and application thereof. The preparation method of the compound is simple, the reaction site is obvious, and the reaction process is easy to control; the squarylium cyanine dye has good molar absorption coefficient and photothermal conversion efficiency, can be used for photoacoustic imaging and photothermal therapy of tumor detection, has good fluorescence quantum yield, and can be used for fluorescence imaging of tumor detection.

Description

(1) Technical field [0001] The invention belongs to the technical field of squaraine dyes, and in particular relates to squaraine dyes, a preparation method thereof and applications in photoacoustic and fluorescent imaging of tumors and photothermal therapy. (2) Background technology [0002] Accurate detection, diagnosis, and resection of tumors depend on precise imaging systems. Compared with traditional biological imaging techniques such as radiation imaging, ultrasound imaging, and magnetic resonance imaging, fluorescence imaging and photoacoustic imaging are more important in diagnosis and guided surgical resection. Its advantages such as high sensitivity and high specificity, low cost, non-invasiveness and better biological safety show great application potential. Many fluorescent materials have also been widely used in fluorescence imaging research, but most of them emit visible light and near-infrared (NIR-I, 750-900nm), which will be absorbed and absorbed to varying...

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): C09B23/01C09B23/10C07D209/90C09K11/06A61K41/00A61K49/00A61K49/22A61P35/00
CPCC07D209/90C09B23/0066C09B23/105C09K11/06A61K49/0021A61K49/226A61K41/0052A61P35/00C09K2211/1029
Inventor 唐龙光凌铭健
Owner THE FOURTH AFFILIATED HOSPITAL OF ZHEJIANG UNIV SCHOOL OF MEDICINE