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Near-infrared fluorescent small molecular probe and preparation and application thereof

A small molecule probe, near-infrared technology, applied in the field of near-infrared imaging, can solve the problems of no target specificity, complicated operation, high cost and so on

Active Publication Date: 2020-04-28
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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  • Near-infrared fluorescent small molecular probe and preparation and application thereof
  • Near-infrared fluorescent small molecular probe and preparation and application thereof
  • Near-infrared fluorescent small molecular probe and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0029] The preparation method of a kind of 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 preparation method of 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 under 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 by 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, post-treatment The target product 4 was obtained with a yield of 55%; 1 H NMR (500MHz, Chloroform-d) δ8.48(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, 4H), 3....

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 sodium bicarbonate solid was added, and 10 ml of acetonitrile containing 1.42 g of methyl iodide was added dropwise under 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 by post-processing, with a yield of 83%;

[0036] In the second step, dissolve 0.1g of intermediate 2 in 5ml of DMF, then add 0.12g of 5-diethylamino-2-nitrosophenol (compound 3), and heat the reaction at 100°C. After the reaction is completed, post-treatment The target product 4 was obtained with a yield of 66%; 1 H NMR (500MHz, Chloroform-d) δ8.48(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, 4H), 3.26(s, 3H), 1.27(t,...

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Abstract

The invention relates to the field of near-infrared imaging, in particular to a near-infrared fluorescent small molecular probe and preparation thereof and application of the near-infrared fluorescentsmall molecular probe in the field of myelin sheath imaging. The structural formula of the small molecular probe is shown in the following figure, and fluorescence performance tests show that the emission wavelength of the small molecular probe is greater than 650nm, and the small molecular probe enters a near-infrared region. Meanwhile, the small molecular probe can be effectively combined witha myelin sheath part, the imaging effect of the myelin sheath part is remarkably enhanced, the small molecular probe can be applied to myelin sheath imaging under the near-infrared condition, and a brand-new method can be provided for diagnosis and curative effect evaluation of central nervous system diseases such as multiple sclerosis.

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 an application thereof 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 spatial and temporal resolution, low cost, safety and speed. Some components of organisms (such as melanin, hemoglobin, cytochrome, etc.) have higher absorption or scattering of visible light bands, which will lead to poor tissue penetration of visible light, and biological tissues in this band have certain autofluorescence interference. In contrast, blood and human tissue have low absorption and scattering of 650-900nm near-infrared (NIR) light, so near-infrared fluorescence can easily pass through ...

Claims

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Application Information

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Patent Type & Authority Applications(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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