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Easily-modified near-infrared region II organic small molecule dye and synthetic method and application thereof

A near-infrared, small molecule technology, applied in the field of bioluminescence imaging, which can solve the problems of low yield and difficult synthesis

Inactive Publication Date: 2019-03-12
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of this type of molecule uses a large number of suzuki coupling methods, which is difficult to synthesize and the yield is low

Method used

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  • Easily-modified near-infrared region II organic small molecule dye and synthetic method and application thereof
  • Easily-modified near-infrared region II organic small molecule dye and synthetic method and application thereof
  • Easily-modified near-infrared region II organic small molecule dye and synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] The synthetic route of the small molecule dye 5H5 in the second near-infrared region is as follows:

[0071]

[0072]

[0073] 1) In a 500mL round bottom flask, dissolve p-hydroxyacetophenone (100mmol, 13.6g) in 200mL of methanol, add potassium hydroxide solution (50%W / W, 70mL) under ice-water bath conditions at 0°C, stir and mix Mix well to fully dissolve. Another benzaldehyde (100 mmol, 10.6 g) was dissolved in 30 mL of methanol, placed in a constant pressure dropping funnel and added dropwise to the above reaction solution. Stir at 0°C for 1 h, then turn to room temperature and stir the reaction overnight. The reaction was stopped, methanol was removed using a rotary evaporator, and 3M hydrochloric acid solution was added dropwise to the remaining solution until pH = 7, and a large amount of yellow solid was precipitated. The filter residue was collected by filtration, and recrystallized from methanol to obtain 18.8 g of light yellow crystals, which were 1-(4...

Embodiment 2

[0085] The synthetic route of the small molecule dye 5L5 in the second near-infrared region is as follows:

[0086]

[0087] 1) In a 100mL round bottom flask, add furochloric acid (10mmol, 1.68g) dissolved in 10mL ethanol. Aniline (22mmol, 2mL) was dissolved in 10mL of ethanol, dropped into the above solution through a constant pressure dropping funnel within 0.5h, and stirred at room temperature for 5h. The reaction solution was concentrated by rotary evaporation to 5 mL, and then poured into 100 mL of diethyl ether, a large amount of golden solid was precipitated, filtered, washed twice with 10 mL of ice ethanol, the filter residue was collected, and dried in vacuo to obtain 1.6 g of golden solid, which was compound 5b. Yield 62%.

[0088] 2) Compound 4a (0.02 mmol, 8.6 mg), compound 5b (0.01 mmol, 2.9 mg) and sodium acetate (0.02 mmol, 1.6 mg) were dissolved in 1 mL of acetic anhydride and reacted at 70°C for 2 h. After cooling to room temperature, the reaction solutio...

Embodiment 3

[0095] The synthesis route of the small molecule dye 6H6 in the second near-infrared region is as follows:

[0096]

[0097] 1) Dissolve cyclohexanone (10mmol, 1.03mL) and tetrahydropyrrole (10mmol, 0.84mL) in 20mL of benzene in a 25mL round bottom flask, connect it to a Dean-Stark trap, and reflux for 4 hours. The solvent was removed by rotary evaporation, the residue was dissolved in 1,4-dioxane, compound 2 (5 mmol, 1.31 g) was added, and the reaction was refluxed for 2 h. The reaction was cooled to room temperature, added water 30 mL, extracted with ethyl acetate (3x10 mL). The organic phases were combined and dried over anhydrous sodium sulfate. Spin dry and pass through a column (200-300 mesh silica gel column, n-hexane / ethyl acetate, 5 / 1, v / v). 1.23 g of compound 3b was obtained as a white solid. Yield 68%. Further HPLC preparation separated and purified two isomers, which were only used for NMR characterization.

[0098] 2) Dissolve compound 3b (2mmol, 0.36g) in...

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Abstract

The invention provides an easily-modified near-infrared region II organic small molecule dye and a synthetic method and application of the easily-modified near-infrared region II organic small molecule dye. The near-infrared region II fluorescent dye belongs to polymethenyl pyran or polymethenyl thiapyran salt organic small molecules, and is prepared by a condensation reaction of polymethenyl aniline salt with pyran or thiopyran salt. The synthetic raw materials are easy to obtain, the cost is low, the preparation process is simple, the yield is high, and large-amount synthesis can be achieved. The purpose of adjusting the fluorescence emission spectrum is achieved by changing an intramolecular polymethenyl chain and hetero atom species. The small molecule dye has the maximum emission wavelength range of 1000-1200 nm, and is high in fluorescence quantum yield, good in light stability and quite applicable to living imaging. The small molecule dye can be linked to groups with specific functions by click chemistry for a variety of bioimaging application. Near-infrared region II fluorescent living imaging achieves low background noise, strong fluorescence signal and high signal-to-noise ratio.

Description

technical field [0001] The invention belongs to the field of biological fluorescence imaging, and in particular relates to an easily modified near-infrared second region organic small molecule dye and its synthesis method and application. Background technique [0002] Optical fluorescence imaging uses fluorescence to image organisms. As a non-invasive and non-radioactive imaging method, it has a powerful ability to detect diseases and track the effects of disease treatments. Compared with other imaging methods, optical imaging has both high time resolution and spatial resolution, and can easily realize real-time dynamic long-term continuous observation of pathological processes. Its research cost is much lower than that of MRI or PET imaging, it has extremely high research value, and has been widely used in various biological imaging applications. [0003] Optical imaging, which uses fluorescence for imaging, has obvious shortcomings, but this shortcoming can be improved to...

Claims

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Application Information

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IPC IPC(8): C07D333/78C07D307/80C09K11/06C09B57/00A61K49/00G01N21/64
CPCA61K49/0021A61K49/0093C07D307/80C07D333/78C09B57/00C09K11/06C09K2211/1007C09K2211/1088C09K2211/1092G01N21/6428G01N2021/6432G01N2021/6439
Inventor 洪学传肖玉玲丁兵兵周晖
Owner WUHAN UNIV
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