Novel fluorescent dye synthetic method with aggregation-induced emission phenomenon

A technology of aggregation-induced luminescence and fluorescent dyes, applied in the field of high-performance functional compounds and their preparation, can solve the problems of unfavorable fluorescence sensing and imaging, improving the difficulty of biomolecular tracking analysis, and reducing the sensitivity of probes

Inactive Publication Date: 2018-09-21
天津市第一中心医院 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no doubt that the ACQ effect is not conducive to fluorescence sensing and imaging. It forces researchers to use only relatively dilute probe solutions in biosensing and imaging research, which leads to a decrease in probe sensitivity and improves the sensitivity of the probe. Difficulty in Tracking and Analysis of Biomolecules

Method used

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  • Novel fluorescent dye synthetic method with aggregation-induced emission phenomenon
  • Novel fluorescent dye synthetic method with aggregation-induced emission phenomenon
  • Novel fluorescent dye synthetic method with aggregation-induced emission phenomenon

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (E)-2-((2-(2-(5-((4'-(2,2-bis(4-methoxyphenyl)-1-phenylvinyl)-[1,1'-biphenyl]-4-yl Synthesis of )methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetamido)ethyl)disulfanyl)ethylnitrate

[0027]

[0028] (1) Synthetic intermediate

[0029] 4,4'-(2-(4-bromophenyl)-2-phenylethene-1,1-diyl)bis(methoxybenzene) [1a]:

[0030] Suspend 24.2g (372mmol) of zinc powder in 250mL of tetrahydrofuran (THF) into a 1L three-necked flask, stir with a magnet and blow in argon. The system was lowered to 0°C and 21mL (186mmol) of titanium tetrachloride was added dropwise. After the dropwise addition, the system was returned to room temperature and reacted for 30min, then heated in an oil bath to 70°C for 3h. Then it was lowered to 0°C again, and 7.4g (93mmol) of pyridine was added dropwise first, and then 9g (37.2mmol) of 4,4'-dimethoxybenzophenone dissolved in 200mL tetrahydrofuran (THF) and 4-bromo 12.6 g (48.4 mmol) of benzophenone, after the dropwise addition, the temperature of the oil...

Embodiment 2

[0061] (E)-2-(2-(2-(7-(4-(2,2-bis(4-methoxyphenyl)-1-phenylvinyl)phenyl)-2,3-dihydrothieno[3,4-b][ 1,4]dioxin-5-yl)vinyl)-4H-chromen-4-ylidene)malononitrile synthesis:

[0062]

[0063](1) Synthetic intermediate 2,3-dihydrothieno[3,4-b][1,4]dioxine-5-carbaldehyde [2a]:

[0064] Dissolve 5g (35.21mmol) of 3,4-ethylenedioxythiophene in 70mL of N,N-dimethylformamide (DMF) into a two-neck flask, stir with a magnet and blow in argon. The reaction system was lowered to 0° C., and 10.8 g (70.42 mmol) of phosphorus oxychloride was added dropwise to the system. The system was slowly restored to room temperature for 8 hours overnight. After the reaction is complete, use a rotary evaporator to spin dry the DMF, lower the system to 0°C and add 50 mL of saturated sodium bicarbonate solution to quench the excess phosphorus oxychloride, use 3*50 mL of dichloromethane to extract and separate the liquid, and spin dry the organic Mutually. The sample was mixed with silica gel and passed ...

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Abstract

The invention relates to a novel fluorescent dye synthetic method with an aggregation-induced emission phenomenon, which relates to the field of material science. A general formula of the obtained fluorescent dye structure is one of the following formulas: (shown in the description). Compared with the traditional fluorescent dye, the novel dye in the invention not only can solve the problem of theaggregation-induced quenching under high concentration, and can perform the tracing monitoring on a release process of functional groups such as NO connected onto the dye by virtue of the regeneration of fluorescent molecules; and meanwhile, a cancer part can be treated by virtue of ROS generated by fluorescent molecules, so that a multifunctional purpose of the dye can be realized.

Description

technical field [0001] The invention relates to the field of material science, in particular to a tetraphenylethylene structure-containing high-performance functionalized compound (especially a compound with singlet oxygen generation ability) for synthesizing aggregation-induced luminescent phenomenon and a preparation method thereof. Background technique [0002] Malignant tumors seriously endanger the life and health of our people. The 2017 China Cancer Statistics Report pointed out that the morbidity and mortality of cancer in my country continue to rise, and it has become the most important cause of disease death; new cancer cases in China account for a quarter of the world. Therefore, improving the level of early diagnosis and precise diagnosis and treatment of cancer is in line with the major strategic needs of our country today. Molecular imaging is a new discipline produced by the combination of traditional medical imaging technology and modern molecular biology. I...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/36C07D495/04C09K11/06C09B23/14A61K49/00A61K41/00A61P35/00G01N21/64
CPCA61K41/0057A61K49/0021A61P35/00C07D277/36C07D495/04C09B23/14C09K11/06C09K2211/1007C09K2211/1037C09K2211/1088C09K2211/1092G01N21/6428G01N2021/6432
Inventor 刘谦倪翔丁丹高贺麒
Owner 天津市第一中心医院
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