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Fluoro-boron formazan near-infrared-II fluorescent dye, preparation method and application

A fluorescent dye and fluorescent probe technology, applied in the field of preparing the fluorescent dye, can solve the problems of limited synthesis steps, high synthesis cost, low reaction yield and the like

Active Publication Date: 2021-07-06
ZHEJIANG PROVINCIAL PEOPLES HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the fluorescence emission spectra of traditional fluorescent dyes are mostly in the near-infrared region, which is limited by complex synthesis steps, high synthesis costs and low reaction yields, so they are not very competitive.

Method used

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  • Fluoro-boron formazan near-infrared-II fluorescent dye, preparation method and application
  • Fluoro-boron formazan near-infrared-II fluorescent dye, preparation method and application
  • Fluoro-boron formazan near-infrared-II fluorescent dye, preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0036] Synthesis of embodiment 1 formula (I) compound

[0037] The synthetic route is as follows:

[0038]

[0039] The specific operation steps are as follows:

[0040] (1) Choose a two-necked flask (500mL), dissolve 1-naphthylaminobenzene (10.96g, 50mmol) and potassium carbonate (13.79g, 100mmol) in dimethyl sulfoxide (200mL), add p-fluoronitrobenzene ( 5.30mL, 50mmol), protected under nitrogen atmosphere, heated and refluxed at 150°C for 48 hours, cooled to room temperature, extracted with ethyl acetate, washed with saturated brine to remove excess DMSO, and distilled under reduced pressure to obtain a brown oily crude product, which was chromatographed on silica gel Column purification (dichloromethane:petroleum ether=1:4) gave an orange oily semi-solid, i.e. intermediate (II) (5.78g, yield 34%), and its chemical structural formula is as follows:

[0041]

[0042](2) Select a 250mL two-necked flask, dissolve the intermediate (II) (4.68g, 13.76mmol) and Pd / C catalys...

Embodiment 2

[0047] Embodiment 2 formula (I) compound BDF-Na nanoparticle preparation

[0048] Dissolve the BDF-Na dye of the compound of formula (I) synthesized above in 1 mL of tetrahydrofuran, quickly inject it into the PBS (10 mL) solution containing the amphiphilic matrix poly(styrene)-block-poly(ethylene glycol), and sonicate for 10 minutes, stirred at room temperature for 12 hours, and removed the organic solvent to obtain nano-functionalized BDF-Na organic nanoparticles. as attached image 3 The dynamic light scattering test results of the organic nanomaterial BDF-Na nanoparticles shown show that the hydrated particle size is about 70nm, and the nanoparticles of this size can effectively penetrate the cell membrane and enter the cell smoothly.

Embodiment 3

[0049] Embodiment 3 adopts formula (I) compound BDF-Na photophysical performance test prepared by the present invention

[0050] Add formula (I) compound BDF-Na dichloromethane solution (2.5mL) in the quartz cuvette of ultraviolet test, concentration is 1 * 10 -5 M, test its UV absorption spectrum. The results are attached Figure 4 Shown, the maximum ultraviolet absorption wavelength of formula (I) compound BDF-Na is 770nm in the near-infrared absorption range;

[0051] Add formula (I) compound BDF-Na dichloromethane solution (2.5mL) in the quartz cuvette of fluorescence test, concentration is 1 * 10 -5 M, to test its fluorescence emission spectrum. as attached Figure 5 As shown, the maximum fluorescence emission wavelength of the compound BDF-Na of formula (I) is 1017nm, and it absorbs in the second near-infrared region. In addition, using IR1061 (1.7%, dichloromethane solution; Chem. Phys. Lett. 2003, 373, 372-378) as a reference, the measured fluorescence quantum yie...

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Abstract

The invention relates to a fluorine boron formazan near-infrared-II fluorescent dye, a preparation method and application. Particularly, the fluorescent dye has good photophysical properties, the maximum absorption wavelength of an ultraviolet absorption spectrum in a dichloromethane solution is 770nm, and the fluorescent dye has strong fluorescence emission between 900-1200nm. The fluorescent dye has the advantages of small molecular weight, good biocompatibility, long emission wavelength, high quantum efficiency, good targeting property, large imaging depth and the like, and can be applied to the aspects of biological imaging, fluorescent probes, laser dyes, fluorescent sensors, fluorescent labels, near-infrared photodynamics, photovoltaic cells, tumor treatment and the like.

Description

technical field [0001] The invention belongs to the technical field of biomaterials, and in particular relates to a fluoroboronformin-based near-infrared second-zone fluorescent dye used in biological imaging, fluorescent probes, laser dyes, fluorescent sensors, fluorescent labels, near-infrared photodynamics, photovoltaic cells and tumors. Application in therapy; the present invention also provides a method for preparing the fluorescent dye. Background technique [0002] At present, common molecular imaging techniques such as tomography imaging (CT), ultrasound imaging (US), X-ray and magnetic resonance imaging (MRI) are used for medical diagnosis of diseases, etc. However, these common methods still have defects, For example, the spatial resolution is poor, and dynamic real-time monitoring cannot be performed. Fluorescence imaging technology has been widely used in the fields of life science and medicine due to its characteristics of non-invasiveness, real-time, small amo...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06C09B57/00A61K41/00A61K49/00A61P35/00
CPCC07F5/022C09K11/06C09B57/00A61K49/0021A61K41/0057A61P35/00C09K2211/1085
Inventor 牟晓洲董晓臣邵进军屠越兴叶祥明蔡宇程子矜
Owner ZHEJIANG PROVINCIAL PEOPLES HOSPITAL
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