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Modifiable fluorescent compound, synthesis method thereof and application of modifiable fluorescent compound as near-infrared II-region reporter molecule

A compound and near-infrared technology, applied in the field of fluorescent compounds, can solve problems such as biocompatibility, poor druggability, rare research reports, and no post-modification, etc., to improve water solubility and biocompatibility, good imaging effect, and broad field The effect of applying the foreground

Active Publication Date: 2014-08-13
武汉绿海棕生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the poor water solubility of its structure itself, it cannot be modified later, and its biocompatibility and druggability are poor. So far, there are few research reports on its use in fluorescence imaging.

Method used

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  • Modifiable fluorescent compound, synthesis method thereof and application of modifiable fluorescent compound as near-infrared II-region reporter molecule
  • Modifiable fluorescent compound, synthesis method thereof and application of modifiable fluorescent compound as near-infrared II-region reporter molecule
  • Modifiable fluorescent compound, synthesis method thereof and application of modifiable fluorescent compound as near-infrared II-region reporter molecule

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1: Synthesis (1a)

[0048]

[0049] Take 6.7g (13mmol) of compound (2a), 3.84g (10mmol) of compound (3), 0.5246g (2mmol) of triphenylphosphine, and 2.12g (20mmol) of sodium carbonate into a 50mL round bottom flask. Under nitrogen protection, 30 mL of toluene / water mixture (v / v, 8:2) was added. Nitrogen gas was passed into the reaction liquid, oxygen in the reaction liquid was excluded for 20 min, and tetrakis(triphenylphosphine) palladium 1.1556 g (1 mmol) was added, and nitrogen gas was continuously passed into the reaction liquid for 10 min. Under the protection of nitrogen, the reaction was heated to reflux for 24h. After the reaction, ethyl acetate (EA) (15 mL×3) was added for extraction three times, the organic phases were combined and washed twice with water (10 mL×2). The organic phase was dried with anhydrous magnesium sulfate for 1 h, filtered, and the filtrate was spin-dried and passed through a silica gel column to obtain 5.895 g of the reacti...

Embodiment 2

[0052] Embodiment 2: synthesis (1b)

[0053]

[0054] Take compound (2b) 7.53g (13mmol), compound (3) 3.84g (10mmol), triphenylphosphine 0.5246g (2mmol), sodium carbonate 2.12g, 20mmol into a 50mL round bottom flask. Under nitrogen protection, 30 mL of toluene / water mixture (v / v, 8:2) was added. Nitrogen gas was passed into the reaction solution, and the oxygen in the reaction solution was excluded for 20 minutes, then 1.1556 g (1 mmol) of tetrakis(triphenylphosphine) palladium was added, and nitrogen gas was continuously passed into the reaction solution for 10 minutes. Under the protection of nitrogen, the reaction was heated to reflux for 48h. After the reaction was completed, EA (15 mL×3) was added for extraction three times, the organic phases were combined and washed twice with water (10 mL×2). The organic phase was dried with anhydrous magnesium sulfate for 1 h, filtered, and the filtrate was spin-dried and passed through a silica gel column to obtain 6.724 g of a ...

Embodiment 3

[0057] Embodiment 3: synthesis (1c)

[0058]

[0059] Take 9.12g (13mmol) of compound (2c), 3.84g (10mmol) of compound (3), 0.5246g (2mmol) of triphenylphosphine, and 2.12g (20mmol) of sodium carbonate into a 50mL round bottom flask. Under nitrogen protection, 30 mL of toluene / water mixture (v / v, 8:2) was added. Nitrogen gas was passed into the reaction liquid, oxygen in the reaction liquid was excluded for 20 min, and tetrakis(triphenylphosphine) palladium 1.1556 g (1 mmol) was added, and nitrogen gas was continuously passed into the reaction liquid for 10 min. Under the protection of nitrogen, the reaction was heated to reflux for 6h. After the reaction was completed, EA (15 mL×3) was added for extraction three times, the organic phases were combined and washed twice with water (10 mL×2). The organic phase was dried with anhydrous magnesium sulfate for 1 h, filtered, and the filtrate was spin-dried and passed through a silica gel column to obtain 6.94 g of a reaction in...

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Abstract

The invention discloses a modifiable fluorescent compound with the maximum emission wavelength range of 1000-1600nm (the II region of a near infrared window) and a preparation method of the modifiable fluorescent compound. A modifiable group is introduced to a structural compound of a diazosulfide group (D-A-D), the increased modifiable site is connected with a bioactive substance, and furthermore, the water solubility and biological compatibility of the compound are improved. The modifiable fluorescent compound is an organic small-molecular compound and is nontoxic, good in absorbability, extremely good in biocompatibility, extremely high in developing sensitivity, capable of playing an important role in the future medical and optical check, and extremely favorable in application prospect. The compound disclosed by the invention can be used as an infrared window II-region reporter molecule for in-vitro detection and in-vivo imaging and can be used for detecting cell markers and tissue specimens and realizing early diagnosis of diseases, diseases staging, intraoperative navigation treatment, postoperative evaluation of therapeutic efficiency and the like.

Description

technical field [0001] The invention relates to a modifiable fluorescent compound with a maximum emission wavelength of 1000nm-1600nm (near-infrared window II region), which can be used for in vitro detection and in vivo imaging, and belongs to the field of fluorescent probe dyes in the second near-infrared region. Background technique [0002] According to statistics, in China and the world, cancer (also known as malignant tumor) is a major cause of abnormal death of human beings. According to the statistics of the World Health Organization (WHO), the number of cancer deaths in the world in 2007 reached 7.9 million (accounting for about 13% of all deaths). Dr. Bernard Stewart, head of WHO International Cancer Research Council (IARC), predicts that by 2020, the global tumor incidence rate will increase by 50%. What is even more worrying is that data shows that 20% of the world's new cancer patients are in China, and 24% of cancer deaths are in China. At present, only 13% of...

Claims

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Application Information

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IPC IPC(8): C07D513/04C09K11/06G01N21/64A61K49/00
CPCA61K49/0021C07D513/04C09K11/06C09K2211/1037G01N21/6486
Inventor 洪学传程震陈浩邓子新
Owner 武汉绿海棕生物科技有限公司
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