Polymerizable NIR (near infrared) fluorescent dye monomer as well as preparation method and application thereof

A technology of fluorescent dyes and dye monomers, applied in the field of near-infrared fluorescent functional dye monomers, can solve the problems of low quantum yield, biological system instability, low detection sensitivity, etc.

Active Publication Date: 2016-05-25
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this type of probe also has many obvious shortcomings, such as weak hydrophilicity, electrostatic copyability, low quantum yield, biological system instability and low detection sensitivity, etc., which directly affect their application in biological research. Applications
Recent design strategies have overcome some of the limitations of traditional near-infrared organic reagents, such as by encapsulating these near-infrared dyes into nanoparticles or binding to specific ligands, although these nanoparticles are a good platform for specific Versatile detection for imaging and cancer therapy, but it's still only in early clinical applications

Method used

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  • Polymerizable NIR (near infrared) fluorescent dye monomer as well as preparation method and application thereof
  • Polymerizable NIR (near infrared) fluorescent dye monomer as well as preparation method and application thereof
  • Polymerizable NIR (near infrared) fluorescent dye monomer as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0032] Add 105 mg of the compound fluoroborate dye and 84 μL of triethylamine into 20 mL of anhydrous tetrahydrofuran and stir to mix, and slowly add 39 μL of methacryloyl chloride diluted with 1 mL of anhydrous tetrahydrofuran dropwise in an ice-water bath. After 1 h, the ice-water bath was removed, and stirring was continued for 5 h at room temperature. Then the solvent is removed by vacuum rotary distillation, the solid is dissolved in dichloromethane and washed with saturated saline and distilled water, then dried with anhydrous sodium sulfate, the solvent is removed by distillation under reduced pressure, passed through a 200-300-mesh silica gel column, and then washed with a volume ratio of 1 :8 mixed solution of ethyl acetate and sherwood oil was eluted, and the eluate was collected and then distilled under reduced pressure to obtain the near-infrared fluorescent functional dye monomer NFM. Depend on image 3 As shown, the monomer in the solvent is tetrahydrofuran, the...

Embodiment 2

[0034] Applications of near-infrared fluorescent monomers

[0035] The macromolecular chain transfer agent PPEGMA is obtained by RAFT polymerization of poly(ethylene glycol) methacryloyl chloride (PEGMA). PEGMA (3087μL, 6.5mmol), CPDN (36mg, 0.13mmol) and AIBN (10.7mg, 6.5×10-2mmol) were added to the ampoule, and 2mL of 1,4-dioxane was added as a solvent. After deoxygenation, 60°C The reaction was stirred for 5h. Precipitate with a large amount of ice ether, centrifuge (10,000rpm, 13min) to obtain PPEGMA (Mn=20900g / mol). Then use PPEGMA (209mg, 0.010mol) as a macromolecular chain transfer agent, add the synthesized monomer NFM (6.5mg, 0.011mmol) and the hydrophobic monomer DBAM (69.1mg, 0.159mmol), then add AIBN (0.82mg, 0.005mmol) and 1mL of 1,4-dioxane ℃ stirring reaction for 11.75h, after precipitation with a large amount of n-hexane , and then centrifuged (10,000rpm, 13min) to obtain the polymer DDP, the molecular weight Mn=27700g / mol.

[0036] The polymer DDP (20 mg) a...

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Abstract

The invention discloses a polymerizable NIR (near infrared) fluorescent dye monomer as well as a preparation method and application thereof. The NIR fluorescent monomer (NFM) is synethized by firstly reacting a fluorine-boron fluorescent dye with methacryloy chloride and then purifying. The synthetized new NFM provides a new method for controllable synthesis and application of NIR fluorescent polymers and has wide application prospect in in-vivo NIR fluorescent imaging.

Description

technical field [0001] The invention belongs to the technical field of organic compounds and polymer materials, and specifically relates to a new class of monomers, namely NFM and its synthesized near-infrared fluorescent functional dye monomers. Background technique [0002] Near-infrared fluorescence imaging is currently a research hotspot in the field of photochemical molecular imaging. Cells, tissues, and organs are labeled with appropriate fluorescent probes, and fluorescent dyes are excited with red light of a specific wavelength to emit near-infrared fluorescence. Near-infrared fluorescence imaging equipment is used for imaging. Detection can directly detect the physiological process and pathological state occurring in the organism. Near-infrared (650-900nm) dyes are promising in chemical biology because they cause minimal photodamage to the organism, allow deep tissue probing, and minimize background autofluorescence. [0003] Traditional organic NIR dyes, because o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/06C09K11/06A61K49/00A61P35/00C08F283/06C08F230/06C08F220/04
CPCA61K49/0019C08F283/065C09B23/06C09K11/06C09K2211/104C09K2211/1096C08F230/06C08F220/04
Inventor 程振平陈利刘晓东张丽芬朱秀林
Owner SUZHOU UNIV
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