Water-soluble dual-targeting near-infrared fluorescent probe and preparation method thereof

A fluorescent probe and near-infrared technology, applied in the field of near-infrared fluorescent probes, can solve the problems of inability to achieve water solubility, insufficient targeting of intracellular substructures, etc., to ensure biocompatibility and use effects, and simple synthesis steps. , the effect of a simple synthesis route

Active Publication Date: 2021-12-10
西安交通大学口腔医院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

None of the above near-infrared fluorescent molecules can achieve effective water solubility, and there are also deficiencies in targeting intracellular substructures

Method used

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  • Water-soluble dual-targeting near-infrared fluorescent probe and preparation method thereof
  • Water-soluble dual-targeting near-infrared fluorescent probe and preparation method thereof
  • Water-soluble dual-targeting near-infrared fluorescent probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] A method for preparing a water-soluble dual-target near-infrared fluorescent probe, the steps are as follows:

[0045] 1) Synthesis of 1,4-dibromo-2,5-dicarbenyl

[0046] To a suspension of 11.4mmol 1,4-dibromo-2,5-xylene, 15mL acetic acid and 30mL acetic anhydride was slowly added dropwise 11mL concentrated sulfuric acid and 45mmol CrO 3 Granules, the resulting mixture was stirred at 0°C for 8 h, poured into ice water and filtered, the obtained white solid was hydrolyzed with a mixture of 15 mL of water, 15 mL of ethanol and 1.5 mL of sulfuric acid under reflux overnight, and then recrystallized by dichloromethane / n-hexane , to obtain the light yellow solid product 1,4-dibromo-2,5-dicarbenyl, and the synthetic route is shown in the following formula.

[0047]

[0048] The 1,4-dibromo-2,5-dicarboxylate prepared in Example 1, that is, the compound 1 1 The H NMR nuclear magnetic pattern is as follows figure 1 as shown, 1 H NMR (400MHz, CDCl 3 ,295K) δ10.39(s,2H),8...

Embodiment 2

[0064] A method for preparing a water-soluble dual-target near-infrared fluorescent probe, the steps are as follows:

[0065] 1) Synthesis of 1,4-dibromo-2,5-dicarbenyl (1)

[0066] To a suspension of 11.8mmol 1,4-dibromo-2,5-xylene, 15.5mL acetic acid and 31mL acetic anhydride was slowly added dropwise 11.4mL concentrated sulfuric acid and 46.5mmol CrO 3 particles. The resulting mixture was stirred at 0 °C for 9 h, poured into ice water and filtered. A mixture of the obtained white solid and 15.5 mL of water, 15.5 mL of ethanol and 1.55 mL of sulfuric acid was hydrolyzed under reflux overnight, and then recrystallized by dichloromethane / n-hexane to obtain a pale yellow solid product 1,4-dibromo-2, 5-two Tsuen base.

[0067]

[0068] 2) Synthesis of compound 2

[0069] 3.1mmol 1,4-dibromo-2,5-dicarboxylate and 6.8mmol 2-(pyridin-4-yl)acetonitrile hydrochloride were dissolved in a mixed solution of 20.5mL ethanol and 20.5mL dichloromethane, then 13.5 mmol of triethylami...

Embodiment 3

[0078] A method for preparing a water-soluble dual-target near-infrared fluorescent probe, the steps are as follows:

[0079] 1) Synthesis of 1,4-dibromo-2,5-dicarbenyl (1)

[0080] To a suspension of 11.6mmol 1,4-dibromo-2,5-xylene, 15.2mL acetic acid and 30.5mL acetic anhydride was slowly added dropwise 11.2mL concentrated sulfuric acid and 46mmol CrO 3 (4.5~4.65g, 45~46.5mmol) granules. The resulting mixture was stirred at 0 °C for 8.5 h, poured into ice water and filtered. A mixture of the obtained white solid and 15.2 mL of water, 15.2 mL of ethanol and 1.52 mL of sulfuric acid was hydrolyzed under reflux overnight, and then recrystallized by dichloromethane / n-hexane to obtain a pale yellow solid product 1,4-dibromo-2, 5-two Tsuen base.

[0081]

[0082] 2) Synthesis of Compound 2

[0083] Dissolve 3.15mmol 1,4-dibromo-2,5-dicarboxylate, 6.93mmol 2-(pyridin-4-yl)acetonitrile hydrochloride in a mixed solution of 21mL ethanol and 21mL dichloromethane, and then add 13...

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Abstract

The invention discloses a water-soluble dual-targeting near-infrared fluorescent probe and a preparation method thereof, and belongs to the field of near-infrared fluorescent probes. According to the water-soluble dual-targeting near-infrared fluorescent probe, stilbene is taken as a structural unit and is modified with cyano groups with electron withdrawing capability, and morpholine groups with electron donating capability are conjugated and linked to two sides of a central benzene ring, so an A-pi-D-pi-A structure is formed in a fluorescent molecule, and the molecule has obvious near-infrared fluorescence emission. The near-infrared fluorescent probe disclosed by the invention is large in Stokes shift, has the characteristics of water solubility and lysosome and DNA dual targeting, and has an important application prospect in the aspects of biological imaging and near-infrared fluorescent probes. The near-infrared fluorescent probe provided by the invention has good water solubility, solves the problem of hydrophobicity of most near-infrared molecules, and can effectively ensure the biocompatibility and use effect of the probe in the use process.

Description

technical field [0001] The invention belongs to the field of near-infrared fluorescent probes, in particular to a water-soluble double-targeting near-infrared fluorescent probe and a preparation method thereof. Background technique [0002] After entering the 21st century, cancer has become one of the major diseases threatening human health. How to effectively realize the imaging of tumor is very critical to the treatment of cancer. Fluorescence imaging technology is a non-invasive, non-radiation-hazardous, high-sensitivity, high-selectivity, and visual detection technology that can be imaged in real time, so it is widely used in the field of biomedical imaging. Compared with fluorescent molecules whose emission range is in the visible region, near-infrared fluorescent molecules have the advantages of deep penetration depth, low background noise, and small tissue damage, and have gradually become the focus of research in the field of fluorescence imaging. [0003] Consider...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/57C09K11/06G01N21/64
CPCC07D213/57C09K11/06G01N21/64C09K2211/1029C09K2211/1033
Inventor 孙俊毅张明明宋忠孝马凌志
Owner 西安交通大学口腔医院
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