Fluorescent probe for tumor diagnosis and treatment as well as preparation method and application of fluorescent probe

A fluorescent probe and tumor technology, applied in preparations for in vivo experiments, chemical instruments and methods, medical preparations containing active ingredients, etc., can solve the problem of poor tumor targeting effect, reduced application, and metabolism of mesoporous nanomaterials Poor ability and other issues

Inactive Publication Date: 2019-03-01
SHENZHEN INST OF ADVANCED TECH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, if you want to use nanosystems for clinical diagnosis and treatment in a safer, more reliable, efficient and low-toxicity way, you need to conduct in-depth exploration of many basic issues in nanosystems to overcome the bottleneck problems faced by common nanomaterials, such as: quantum Nano-gold/silver particles are inorganic heavy metal materials, which are easy to accumulate in living organisms and difficult to degrade; nano-gold/silver particles have a great impact on normal cell activities and metabolism in vivo, and the particle size and shape are greatly affected by the environment, which greatly reduces Its application in the field of tumor diagnosis an...

Method used

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  • Fluorescent probe for tumor diagnosis and treatment as well as preparation method and application of fluorescent probe
  • Fluorescent probe for tumor diagnosis and treatment as well as preparation method and application of fluorescent probe
  • Fluorescent probe for tumor diagnosis and treatment as well as preparation method and application of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0113] Dissolve ethylenediamine (0.67mL, 10mmol) in 10mL ethanol, and heat to reflux;

[0114] 4-(Bromomethyl)pyridinium bromate (1.27 g, 5 mmol) was slowly added to the above solution, heated to reflux for 12 hours, and the solvent was spin-dried, and the obtained solid was dissolved in DMF (20 mL);

[0115] Then, add IR-783 (3.2g, 5mmol), triethylamine (2.77mL, 20mmol), heat to 40°C, and react for 5 hours under nitrogen protection;

[0116] Rotate off the solvent, dry in vacuo for 12 hours, pass through a silica gel column, dichloromethane:methanol=20:1, gradient elution, remove the solvent to obtain 12.06 mg of a dark blue solid product, which is the target product IR-PY, with a yield of 32%.

[0117] The synthetic route of embodiment 1 is referred to as follows:

[0118]

[0119] Example 1 product nuclear magnetic detection collection spectrum is as figure 1 As shown, among them, 1 HNMR (400MHz, CDCl 3 );δ=8.57(d,J=5.5Hz,2H),7.72(d,J=13.1Hz,2H),7.52(d,2H),7.29(s,2H)...

Embodiment 2

[0122] Dissolve ethylenediamine (1.34mL, 20mmol) in 20mL ethanol and heat to reflux;

[0123] 4-(Bromomethyl)pyridinium bromide (2.53 g, 10 mmol) was slowly added to the above solution, heated to reflux for 18 hours, and the solvent was spin-dried, and the obtained solid was dissolved in DMF (40 mL);

[0124] Then, add IR-783 (6.4g, 10mmol), triethylamine (4.54mL, 40mmol), heat to 50°C, and react for 8 hours under nitrogen protection;

[0125] Rotate off the solvent, dry in vacuo for 12 hours, pass through a silica gel column, dichloromethane: methanol = 20:1, gradient elution, remove the solvent, and obtain 20.35 mg of a dark blue solid product with a yield of 27%.

Embodiment 3

[0127] Dissolve ethylenediamine (6.7mL, 100mmol) in 100mL ethanol and heat to reflux;

[0128] 4-(Bromomethyl)pyridinium bromide (12.7 g, 50 mmol) was slowly added to the above solution, heated to reflux for 24 hours, and the solvent was spin-dried, and the obtained solid was dissolved in DMF (100 mL);

[0129] Then, add IR783 (32g, 50mmol), triethylamine (27.7mL, 200mmol), heat to 40°C, and react under nitrogen protection for 24 hours;

[0130] The solvent was spun off, dried in vacuo for 12 hours, passed through a silica gel column, dichloromethane:methanol=20:1, gradient elution, and the solvent was removed to obtain 86.68 mg of a dark blue solid product with a yield of 23%.

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Abstract

The invention provides a fluorescent probe for tumor diagnosis and treatment as well as a preparation method and an application of the fluorescent probe. In the fluorescent probe, an azacyclo structure base is taken as an H<+> receptor, a near infrared fluorescent dye with high extinction coefficient and tumor targeting effect is taken as a fluorophore, then the OFF-ON type probe capable of regulating fluorescence intensity by rapid PET (photoinduced electron transfer) process is formed, fluorescence of the probe is strengthened in a slightly acidic environment of tumor, tumor detection is realized, the probe has strong PA (photoacoustic) signals at the tumor while fluorescence imaging is performed, and tumor boundary can be determined accurately by NIRF/PA bimodal imaging. The fluorescentprobe also has good photo-thermal treatment effect on the tumor and can be used for preparing corresponding tumor treatment drugs.

Description

technical field [0001] The present invention relates to the field of drugs for tumor diagnosis and treatment, in particular to a fluorescent probe for tumor diagnosis and treatment as well as its preparation method and application. Background technique [0002] Cancer is one of the biggest killers threatening human life around the world, and it is also a major challenge in the field of current medical research. How to effectively prevent and treat cancer has become a top priority in scientific research. [0003] Clinically, cancer is mainly treated by three methods: surgery, radiation therapy and chemotherapy. However, surgical treatment has defects such as high risk, large trauma, and prone to complications; while radiotherapy and chemotherapy kill cancer cells, they will also cause serious damage to normal cells in the human body, greatly reducing the survival of patients. quality. Therefore, the development of efficient and low-toxic treatment methods is of great signi...

Claims

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Application Information

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IPC IPC(8): C07D401/14C09K11/06A61K49/00A61K49/22A61K41/00
CPCA61K41/0052A61K49/0021A61K49/22C07D401/14C09K11/06
Inventor 蔡林涛孟晓青龚萍孙枝红
Owner SHENZHEN INST OF ADVANCED TECH CHINESE ACAD OF SCI
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