A near-infrared fluorescent small molecule probe and its preparation and application

A small-molecule probe and near-infrared technology, applied in the field of near-infrared imaging, can solve the problems of complex operation, lack of targeting specificity, and high cost

Active Publication Date: 2022-06-24
NANJING POLYTECHNIC INSITUTE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the current MS diagnosis technology, it mainly relies on magnetic resonance imaging technology, which does not have target specificity, and has the disadvantages of complicated operation and high cost.

Method used

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  • A near-infrared fluorescent small molecule probe and its preparation and application
  • A near-infrared fluorescent small molecule probe and its preparation and application
  • A near-infrared fluorescent small molecule probe and its preparation and application

Examples

Experimental program
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Effect test

preparation example Construction

[0029] The method for preparing a near-infrared fluorescent small molecule probe is characterized in that the solvent described in the first step reaction is methanol, acetonitrile or tetrahydrofuran;

[0030] The method for preparing a near-infrared fluorescent small molecule probe is characterized in that the heating reaction temperature in the second step reaction is 70-120°C.

Embodiment 1

[0032] In the first step, 1.59 g (10 mmol) of 5-amino-1-naphthol (compound 1) was dissolved in 30 ml of methanol, 0.84 g of solid sodium bicarbonate was added, and 10 ml of methanol containing 1.42 g of methyl iodide was added dropwise with stirring The solution was first reacted at room temperature for half an hour, and then refluxed for 4 hours. After the reaction was completed, 5-methylamino-1-naphthol (Intermediate 2) was obtained after post-processing with a yield of 75%;

[0033] In the second step, 0.1 g of intermediate 2 was dissolved in 5 ml of DMF, and then 0.12 g of 5-diethylamino-2-nitrosophenol (compound 3) was added, and the reaction was heated at 70 ° C. After the reaction was completed, after-treatment The target product 4 was obtained with a yield of 55%; 1 H NMR (500MHz, Chloroform-d) δ 8.48 (d, J=9.3Hz, 1H), 8.20 (s, 1H), 7.67 (t, J=7.7Hz, 1H), 7.61 (d, J=9.1Hz) ,1H),7.55(d,J=7.6Hz,1H),6.67(dd,J=9.1,2.7Hz,1H),6.45(d,J=2.6Hz,1H),6.42(s,1H),3.49 (q,J=7.1Hz,4...

Embodiment 2

[0035] In the first step, 1.59 g (10 mmol) of 5-amino-1-naphthol (compound 1) was dissolved in 30 ml of acetonitrile, 0.84 g of solid sodium bicarbonate was added, and 10 ml of acetonitrile containing 1.42 g of methyl iodide was added dropwise with stirring The solution was first reacted at room temperature for half an hour, and then refluxed for 4 hours. After the reaction was completed, 5-methylamino-1-naphthol (intermediate 2) was obtained after post-processing with a yield of 83%;

[0036] In the second step, 0.1 g of intermediate 2 was dissolved in 5 ml of DMF, then 0.12 g of 5-diethylamino-2-nitrosophenol (compound 3) was added, and the reaction was heated at 100 ° C. After the reaction was completed, after-treatment The target product 4 was obtained with a yield of 66%; 1 H NMR (500MHz, Chloroform-d) δ 8.48 (d, J=9.3Hz, 1H), 8.20 (s, 1H), 7.67 (t, J=7.7Hz, 1H), 7.61 (d, J=9.1Hz) ,1H),7.55(d,J=7.6Hz,1H),6.67(dd,J=9.1,2.7Hz,1H),6.45(d,J=2.6Hz,1H),6.42(s,1H),3.49 (q, J=7...

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Abstract

The invention relates to the field of near-infrared imaging, in particular to a near-infrared fluorescent small molecule probe, its preparation, and its application in the field of myelin imaging. The structural formula of this small molecule probe is shown in the figure below. After the fluorescence performance test, its emission wavelength is greater than 650nm and enters the near-infrared region. At the same time, this small molecule probe can effectively combine with the myelin sheath and significantly enhance the imaging effect of the myelin sheath. Efficacy evaluation provides a new method.

Description

technical field [0001] The invention relates to the field of near-infrared imaging, in particular to a near-infrared fluorescent small molecule probe, a preparation method thereof, and its application in the field of myelin imaging. Background technique [0002] Fluorescence imaging technology has been widely used in many fields such as tumor diagnosis, biomolecular detection, drug distribution and metabolism due to its advantages of non-invasiveness, visualization, high temporal and spatial resolution, low cost, safety and rapidity. Some components of the organism (such as melanin, hemoglobin, cytochrome, etc.) have high absorption or scattering in the visible light band, which will lead to poor tissue penetration of visible light, and biological tissues have certain autofluorescence in this band. interference. In contrast, blood and human tissues have low absorption and scattering of near-infrared (NIR) light at 650-900 nm, so near-infrared fluorescence is easily transmit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D265/34C09K11/06G01N21/359G01N21/64
CPCC07D265/34C09K11/06G01N21/6428G01N21/6486G01N21/359C09K2211/1033
Inventor 李玉龙陈琳蒋蕻孙海燕孙宏顺张庆余施星浩刘莎莉李睿哲
Owner NANJING POLYTECHNIC INSITUTE
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