Preparation of near-infrared dye based on aza-fluoroborane and application

A near-infrared dye and heterofluoroborane technology is applied in the field of near-infrared dye azafluoroborane dyes and the preparation thereof, and achieves the effects of deep tissue penetration, convenient industrial production and abundant raw materials

Active Publication Date: 2018-06-01
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Azafluoroborane dyes are generally used in optical devices, biological imaging and other fields. So far, few people have reported that

Method used

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  • Preparation of near-infrared dye based on aza-fluoroborane and application
  • Preparation of near-infrared dye based on aza-fluoroborane and application
  • Preparation of near-infrared dye based on aza-fluoroborane and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1: Synthesis of Azafluoroborane Photothermal Dye C

[0037]

[0038] Synthesis of compound 1

[0039] Take a clean two-necked bottle, add magneton, 2.44g of p-hydroxybenzaldehyde (about 20mmol), 19.31g of bromooctane (about 100mmol), 13.82g of potassium carbonate and 50ml of anhydrous magnetic stirring, and react at 80°C 24h. After the reaction was completed, water / dichloromethane was extracted several times, and the organic phases were combined. After separation by chromatography column, 4.68 g of light yellow liquid was obtained (the yield was about 99%).

[0040] Synthesis of Compound 2

[0041] Take a clean two-necked bottle, add magneton, 4.68g of 1 (about 20mmol), 4.1g of 2-bromoacetylthiophene (about 20mmol) and 40ml of ethanol solution. Stir until all the solids are dissolved, then slowly add 5ml of sodium hydride solution (containing 1.00g of sodium hydroxide). The reaction was stirred at room temperature for 24 h, and a yellow solid was precipi...

Embodiment 2

[0053] Example 2: Synthesis of Azafluoroborane Photothermal Dye D

[0054] Synthesis of Compound D

[0055] Take a clean 50ml one-mouth bottle, add magneton, 0.14g (0.15mmol) 5, and 10mL dry dichloromethane to dissolve. At 0°C, after adding 0.107g (0.60mmol) NBS, stir for 6h. After the reaction, the mixed solution was washed with water, washed with saturated sodium chloride, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography to obtain 0.13 g Blue solid product (~80% yield).

[0056] 1 H NMR (400MHz, CDCl 3 ): δ (ppm) = 7.91 (d, J = 4.4Hz, 2H), 7.80 (d, J = 8.8 Hz, 4H), 7.21 (d, J = 4.4Hz, 2H), 6.95 (d, J = 8.8 Hz,4H),4.02(t,J=6.8Hz,4H), 1.86-1.79(m,4H),1.52–1.45(m,4H),1.38–1.29(m,16H),0.92-0.88(m, 6H).

[0057] 13 C NMR (100MHz, CDCl 3 ):δ(ppm)=160.64,148.03,144.68,142.52,135.53,132.51,131.87,131.10,122.87,121.21,114.13,108.82,68.20,33.85,31.90,31.52,30.15,29.56,29.26,26.09,22.69,14.13

[0058] 19 F NMR (37...

Embodiment 3

[0059] Embodiment 3: the test of the molecular weight of C

[0060] Take a small amount of sample C, mix it with the matrix, then apply the sample, and measure it with MALDI-TOF / TOF, as shown in Figure 1, which preliminarily proves the correctness of the C molecule.

[0061] [m / e] (M, MALDI-TOF) theoretical value: 923.62, experimental value: 923.63

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Abstract

The invention discloses preparation of near-infrared dye based on aza-fluoroborane and application. The near-infrared dye is prepared from thiophene-containing groups and a basic aza-fluoroborane framework. The aza-fluoroborane dye is prepared by the following steps: (1) synthesis of ketene: the ketene is obtained by addition-elimination reaction of aldehyde and ketone under an alkali condition; (2) ketene and nitromethane conduct addition reaction under the alkali condition; (3) ring-forming reaction: under the condition with existence of an ammonia source, two times of equivalent ketene andnitromethane conduct ring-forming reaction; (4) coordination reaction: products obtained in the step (3) and metal or boron difluoride are coordinated to obtain a target product. The preparation and the application disclosed by the invention have the advantages that the target dye has strong near-infrared absorption (the molar light absorption coefficient is more than 100000M<-1>cm<-1>), high singlet oxygen yield and good photothermal effect, and can be used for photodynamic and photothermal synergy with single-wavelength excitation for tumor treatment under the guidance of photothermal imaging, photoacoustic imaging and fluorescence imaging.

Description

technical field [0001] The invention belongs to the field of organic photoelectric material technology and biology. It specifically relates to a near-infrared dye azafluoroborane dye with photodynamic and photothermal effects, its preparation method and its application in the fields of fluorescence imaging, photothermal imaging, photoacoustic imaging, photothermal therapy, photodynamic therapy, etc. Applications. Background technique [0002] Cancer threatens human health. Traditional tumor treatment methods, such as surgery, chemotherapy, and radiotherapy, are often accompanied by side effects. Photodynamic therapy and photothermal therapy have attracted widespread attention as non-invasive tumor treatment methods. Image-guided photodynamic therapy and photothermal therapy can precisely treat tumor sites in real time. Greatly improved the effect of tumor treatment. The selection of materials for tumor treatment plays a decisive role in the treatment effect of tumors. ...

Claims

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Application Information

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IPC IPC(8): C09B57/00C09K11/06G01N21/64A61K41/00A61P35/00
CPCA61K41/0052A61K41/0057C09B57/00C09K11/06C09K2211/1055G01N21/64
Inventor 赵强黄维徐云剑刘淑娟赵梦龙冯腾
Owner NANJING UNIV OF POSTS & TELECOMM
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