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pH fluorescent probe based on near-infrared fluorescent dye and its preparation method and application

A technology of fluorescent dyes and fluorescent probes, applied in fluorescence/phosphorescence, luminescent materials, chemical instruments and methods, etc., can solve the problems of slow assembly-disassembly of nanomaterials, difficult adjustment of pH response range, long-term tumor tissue, etc. Accurate and stable imaging effect, good light stability, and the effect of reducing light damage

Active Publication Date: 2022-03-18
NANTONG UNIVERSITY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, these two methods have their own problems. The first method usually uses the assembly-disassembly of nanomaterials to regulate the hydrophilicity and hydrophobicity of nanomaterials to regulate the luminescent properties of small molecule materials. Although this method is very sensitive, However, the assembly-disassembly process of nanomaterials is usually too slow, and it takes a long time to realize the visualization of tumor tissue
Although there are many reports on the second method of constructing pH-responsive probes, so far, the luminescence wavelengths of such probes are mostly concentrated in the visible light band, and there are relatively few small-molecule pH fluorescent probes with luminescence wavelengths above 700nm.
Moreover, most of these probes have low quantum efficiencies, and the pH response range is not easy to control, which limits their application in in vivo imaging.

Method used

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  • pH fluorescent probe based on near-infrared fluorescent dye and its preparation method and application
  • pH fluorescent probe based on near-infrared fluorescent dye and its preparation method and application
  • pH fluorescent probe based on near-infrared fluorescent dye and its preparation method and application

Examples

Experimental program
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Effect test

example 1

[0056] Example 1: Synthesis of near-infrared pH fluorescent probe Rh-SQ1.

[0057] Concrete reaction formula is as follows:

[0058]

[0059] step 1:

[0060] Add 0.5 mmol of rhodamine precursor compound a, squarylium (0.5 mmol) and 0.05 mmol of triethylamine to a three-necked flask equipped with a water separator, add solvent toluene, and heat to reflux for 24 hours under nitrogen protection. The solution turned from yellow to light blue. Stop the heating after the reaction, cool to room temperature, remove the solvent toluene by rotary evaporation, and purify and separate the obtained crude product by column chromatography to obtain rhodamine squarylium intermediate compound b. Wherein the column chromatography developing agent in the column chromatography purification and separation is composed of dichloromethane and petroleum ether with a volume ratio of 1:10.

[0061] The yield of compound b was 75%.

[0062] The NMR of compound b is as follows: 1H NMR (400MHz, CD3...

example 2

[0072] Example 2. Synthesis of near-infrared pH fluorescent probe Rh-SQ2.

[0073] step 1:

[0074] Compound b was synthesized according to the method of Step 1 in Example 1.

[0075] Step 2:

[0076] Mix 2,3,3-trimethylbenzindole, ethyl iodide and potassium carbonate solids and dissolve them in toluene, reflux reaction under nitrogen protection, after the reaction, cool the reaction liquid to room temperature, and filter to obtain the solid phase , and then the solid phase was washed with petroleum ether and then dried to obtain N-ethyl-2,3,3-trimethylbenzindole iodide compound d.

[0077] The yield of compound d was 93%.

[0078] The NMR of compound d is as follows: 1H NMR (400MHz, CDCl3, δ) 8.118(d, J=8.8Hz, 1H), 8.086(d, J=8.8Hz, 1H), 8.058(d, J=8.0Hz, 1H) ,7.822(d,J=8.8Hz,1H),7.752(m,1H),7.684(m,1H),4.872(q,J=7.2Hz,14.8Hz,2H),3.251(s,3H),1.889 (s, 6H), 1.684 (t, J = 7.2Hz, 3H).

[0079] Step 3:

[0080] Add 1mmol rhodamine squarylium intermediate compound b, 1mmol ...

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Abstract

A pH fluorescent probe based on a near-infrared fluorescent dye and a preparation method and application thereof belong to the technical field of analytical chemistry. The fluorescent probe is obtained through a chemical synthesis method, and the invention also discloses the application of the fluorescent probe to selectively detect pH in aqueous solution, cell system, and mouse tumor model. The fluorescent probe of the present invention utilizes the characteristic of rhodamine as a response mechanism that the switch ring is affected by pH, and has the characteristics of near-infrared emission, high sensitivity, fast response speed, good photostability and the like.

Description

technical field [0001] The invention belongs to the technical field of fluorescence imaging. Background technique [0002] Malignant tumors, which are commonly referred to as "cancer", usually start from the mutation of single cells. Along with the canceration of cells to form tumors, these cells are constantly changing themselves and their surrounding growth environment, gradually forming an environment with unique physiological characteristics of tumor tissue, which is usually called the tumor microenvironment. The tumor microenvironment includes not only tumor cells themselves, but also vascular endothelial cells, lymphatic endothelial cells, mesenchymal cells, immune cells, and extracellular matrix. Factors such as abnormal tumor proliferation and hypoxia cause the increase of anaerobic metabolism of tumor cells, which in turn generates a large amount of lactic acid in the cells and causes the imbalance of pH homeostasis in the tumor microenvironment. It is also a hall...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D405/08G01N21/64A61K49/00
CPCC09K11/06C07D405/08G01N21/6428A61K49/0032C09K2211/1007C09K2211/1029C09K2211/1088
Inventor 周晓波吴丽冀海伟刘金霞秦玉岭
Owner NANTONG UNIVERSITY
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