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A kind of 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 insufficient substructure in targeted cells and inability to achieve water solubility, achieve simple synthesis steps, ensure biocompatibility and use effects , the effect of a simple synthesis route

Active Publication Date: 2022-07-01
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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  • A kind of water-soluble dual-targeting near-infrared fluorescent probe and preparation method thereof
  • A kind of water-soluble dual-targeting near-infrared fluorescent probe and preparation method thereof
  • A kind of water-soluble dual-targeting near-infrared fluorescent probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] A preparation method of a water-soluble dual-targeting near-infrared fluorescent probe, the steps are as follows:

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

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

[0047]

[0048] The 1,4-dibromo-2,5-dialdehyde benzene prepared in Example 1 is the compound 1 1 H NMR nuclear magnetic map such as figure 1 shown, 1 H NMR (400MHz, CDCl 3 ,295K)δ10.39(s,2H),8.19(s,2H)....

Embodiment 2

[0064] A preparation method of a water-soluble dual-targeting near-infrared fluorescent probe, the steps are as follows:

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

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

[0067]

[0068] 2) Synthesis of compound 2

[0069] 3.1 mmol of 1,4-dibromo-2,5-dialdehyde benzene and 6.8 mmol of 2-(pyridin-4-yl)acetonitrile hydrochloride were dissolved in a mixed solution of 20.5 mL of ethanol and 20.5 mL of di...

Embodiment 3

[0078] A preparation method of a water-soluble dual-targeting near-infrared fluorescent probe, the steps are as follows:

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

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

[0081]

[0082] 2) Synthesis of compound 2

[0083] Dissolve 3.15 mmol of 1,4-dibromo-2,5-dialdehyde benzene and 6.93 mmol of 2-(pyridin-4-yl)acetonitrile hydrochloride in a mixed solution of 21 mL of etha...

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Abstract

The invention discloses a water-soluble double-targeting near-infrared fluorescent probe and a preparation method thereof, and belongs to the field of near-infrared fluorescent probes. The water-soluble double-targeted near-infrared fluorescent probe of the invention takes stilbene as a structural unit, is modified with a cyano group with electron-pulling ability, and is conjugated on both sides of the central benzene ring to link a morpholino group with electron-pulling ability A-π-D-π-A structure is formed in the fluorescent molecule, so that the molecule has obvious near-infrared fluorescence emission. The near-infrared fluorescent probe of the invention has the characteristics of large Stokes shift, water solubility, and dual targeting of lysosomes and DNA, and has important application prospects in biological imaging and near-infrared fluorescent probes. The near-infrared fluorescent probe of the present 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 during use.

Description

technical field [0001] The invention belongs to the field of near-infrared fluorescent probes, in particular to a water-soluble double-targeted 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 tumor imaging is very important for cancer treatment. Fluorescence imaging technology is a non-invasive, non-radiative hazard, high-sensitivity, high-selectivity and real-time imaging visualization detection technology, so it is widely used in the field of biomedical imaging. Compared with fluorescent molecules whose emission range is in the visible light 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] Considering the environmen...

Claims

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Application Information

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Patent Type & Authority Patents(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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