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Modifiable second near-infrared window fluorescent imaging probe and preparation method and application thereof

A technology of fluorescent compounds and dichloromethane, which is applied in the fields of biomedical fluorescence imaging and biomedical materials, can solve problems such as interference with fluorescence imaging effects, and achieve broad application prospects, high yield, and the effect of increasing quantum yield.

Active Publication Date: 2017-07-25
武汉振豪生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Biological tissues have strong autofluorescence and severe light absorption in the range of <700nm, which will seriously interfere with the fluorescence imaging effect

Method used

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  • Modifiable second near-infrared window fluorescent imaging probe and preparation method and application thereof
  • Modifiable second near-infrared window fluorescent imaging probe and preparation method and application thereof
  • Modifiable second near-infrared window fluorescent imaging probe and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: the preparation of compound 4a

[0040] Take compound 2a (5.48g, 10mmol), compound 3a (4.81g, 10mmol) and potassium carbonate (3.45g, 25mmol) into a 500mL round bottom flask, add tetrahydrofuran-water (v / v, 5: 1) 300mL, feed argon into the reaction solution and bubble for 5min to get rid of oxygen in the system, add [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex (0.9 g, 1 mmol), heated to reflux in an oil bath at 75° C. for 14 hours under the protection of argon. After the reaction, cool to room temperature, remove THF by rotary evaporation, redissolve the residue in 200 mL of dichloromethane, wash with water (50 mL×3) three times, and wash with saturated brine (50 mL×3) three times. The organic phase was dried with anhydrous magnesium sulfate for 3 hours, filtered, and the filtrate was spin-dried to obtain 7.4 g of compound 4a. Yield: 90%.

[0041] The structure determination data of compound 4a are as follows:

[0042...

Embodiment 2

[0043] Embodiment 2: the preparation of compound 5a

[0044] Take compound 4a (7.4g, 9mmol), compound 3a (4.329g, 9mmol) and potassium carbonate (3.105g, 22.5mmol) into a 500mL round bottom flask, add tetrahydrofuran-water (v / v, 5 : 1) 270mL, in the reaction solution, pass into argon bubble 5min and get rid of oxygen in the system, add [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex ( 0.81g, 0.9mmol), under the protection of argon, heated to reflux in an oil bath at 75°C for 20 hours. After the reaction, cool to room temperature, remove tetrahydrofuran by rotary evaporation, redissolve the residue in 150mL dichloromethane, wash with water (30mL×3) three times, and wash with saturated brine (30mL×3) three times. The organic phase was dried with anhydrous magnesium sulfate for 3 hours, filtered, and the filtrate was spin-dried to obtain 9.08 g of compound 5a. Yield: 92%.

[0045] The structure determination data of compound 5a are as follows: ...

Embodiment 3

[0049] Embodiment 3: the preparation of compound 1a

[0050] Take compound 5a (9.08g, 8.28mmol), zinc powder (64.915g, 993.6mmol) and ammonium chloride (15.947g, 298.08mmol) into a 1000mL round bottom flask, add dichloromethane 300mL and methanol -Water (v / v, 9:1) 300mL mixed solvent, the reaction solution was mechanically stirred at 25°C for 4 hours. After the reaction was finished, filter through diatomaceous earth to remove insoluble solids, add 300mL dichloromethane to wash, collect the filtrate, wash three times with water (100mL×3), wash three times with saturated sodium bicarbonate solution (100mL×3), wash with saturated saline (100mL×3) After washing three times, the organic phase was dried with anhydrous magnesium sulfate for 3 hours, filtered, and the solvent was removed to obtain an intermediate. Under argon protection in a 250mL round bottom flask, the intermediate was added to 160mL of anhydrous pyridine, N-sulfinanilide (9.09g, 66.24mmol) and trimethylchlorosila...

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Abstract

The invention discloses a near-infrared window fluorescent imaging agent containing diazosulfide and a fluorene ring and a preparation method thereof. A modifiable group is introduced into the fluorene ring of the fluorescent compound, increased modifiable sites can be used for connection of different bioactive substances, water solubility and biological compatibility can be improved, and the application range in the biomedical field can be expanded. The fluorescent imaging agent has the advantages of high fluorescence intensity, no toxicity, good biocompatibility, and the like, and has excellent application prospects. The invention also discloses the application of the fluorescent imaging agent in the field of brain glioma, systemic angiography and sentinel lymph node dissection. In addition, the imaging agent has good modificability, and also can be used for in-vitro detection of various disease markers, in-vivo diagnosis and surgical navigation treatment of breast cancer, prostate cancer and colon cancer and other cancer, evaluation of curative effect after tumorectomy, and the like.

Description

technical field [0001] The invention belongs to the field of biomedical materials, and in particular relates to a class of modifiable near-infrared second-region fluorescent probes, a preparation method thereof, and an application in the field of biomedical fluorescence imaging. Background technique [0002] Cancer (also known as malignant tumor) is a serious threat to human health. Due to the limitation of medical technology level, there is currently no effective treatment for advanced cancer, so early diagnosis of cancer is particularly important for patients. Early detection and timely treatment can significantly improve the survival rate of cancer patients. The emergence of molecular imaging technologies such as non-invasive living animal fluorescence imaging technology has opened up a new development path for the early diagnosis of cancer. [0003] In addition, the initial tumor metastasis generally occurs in the sentinel lymph nodes. Sentinel lymph nodes are lymph no...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04C09K11/06A61K49/00
CPCA61K49/0021A61K49/0052A61K49/0054A61K49/0056C07D513/04C09K11/06C09K2211/1051C09K2211/1092
Inventor 田间洪学传曾小东丁明敏
Owner 武汉振豪生物科技有限公司
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