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A targeting material based on indole squaraine dye and its preparation method, fluorescent nanoparticles and its preparation method

A technology of indole squaraine and fluorescent nanotechnology, applied in the field of biomedicine, can solve the problems of weak application in the field of cancer photodiagnosis and treatment, lack of specific tumor targeting ability and cancer treatment ability, and achieve good product stability and biological High safety and high tumor suppression rate

Active Publication Date: 2021-07-13
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the application of indole squaraine dyes in the field of cancer photodiagnosis and therapy is relatively weak due to the lack of specific tumor targeting ability and cancer treatment ability.

Method used

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  • A targeting material based on indole squaraine dye and its preparation method, fluorescent nanoparticles and its preparation method
  • A targeting material based on indole squaraine dye and its preparation method, fluorescent nanoparticles and its preparation method
  • A targeting material based on indole squaraine dye and its preparation method, fluorescent nanoparticles and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: Synthesis of indole squaraine dye ICy5-CPT-RGD for targeted diagnosis and treatment

[0043] 1. Add 2.23g (10mmol) of 4-bromophenylhydrazine hydrochloride and 0.86g (10mmol) of 3-methyl-2-butanone into 10mL of glacial acetic acid, reflux for 12 hours, and evaporate to remove the solvent. Dissolve with dichloromethane and wash with saturated NaHCO3 The aqueous solution was washed repeatedly until the aqueous phase was colorless and the pH was neutral, and the organic phase was removed by rotary evaporation to obtain 1.88 g (7.9 mmol) of 5-bromo-2,3,3-trimethyl-3H-ylindole with a yield of 79%. ;

[0044] 1 H NMR (400MHz, CDCl 3 )δ7.40(s,3H),2.27(s,3H),1.30(s,6H).

[0045] 2. Add 1.19g (5mmol) of 5-bromo-2,3,3-trimethyl-3H-ylindole and 1.08g (5mmol) of p-benyl bromobenzoic acid to 15mL of acetonitrile, reflux for 20 hours, and remove by rotary evaporation After the solvent was precipitated with ether and washed several times, 1.72 g (3.8 mmol) of the interme...

Embodiment 2

[0055] Example 2: ICy5-CPT-RGD prepares nanoparticle PTN by self-assembly method

[0056] Dissolve 2.1 mg of indole squaraine dye ICy5-CPT-RGD in 1 mL of DMSO (1×10 -3 M), 0.1 mL of the dye solution was dropped into 10 mL of water (50° C.), stirred rapidly for 5-10 minutes, and then DMSO was removed by dialysis to obtain an aqueous solution of PTN.

Embodiment 3

[0057] Example 3: PTN nanoparticles for targeted fluorescence imaging of living tumors

[0058] A tumor model of human liver cancer in vitro (BEL-7402) in Balb / c nude mice was established to evaluate the targeting imaging ability and anti-tumor effect of PTN in vivo. The cultured BEL-7402 cells were mixed with 3×10 6 Cells / 100 μL were inoculated subcutaneously at the lower right of the back of nude mice, and cultured until the tumor volume (0.5 × length × width 2 ) is 100mm 3 about. The tumor-bearing mice were injected with 200 μL of PTN (1 mg / mL) solution through the tail vein, and the control group was injected with 200 μL of normal saline. The mice were placed in an IVIS light-shielding incubator, then the mice were anesthetized with 2.5% isoflurane, and images were collected using the IVIS small animal in vivo imaging system (PerkinElmer Co.). The time points for collecting images were 0, 0.5, 1, 3, 6, 12, 18, and 24 hours. After 24 hours, the mice were sacrificed, an...

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Abstract

The invention provides a targeting material based on indole squaraine dye, a preparation method thereof, fluorescent nanoparticles and a preparation method thereof. In the present invention, indole squaraine substituted with bromine, hydrogen or methyl is coupled with targeting polypeptide RGD molecule or with RGD molecule and anticancer drug camptothecin respectively to obtain amphiphilic diagnosis and treatment molecules. Such molecules can self-assemble in water to form stable nanoparticles with uniform size. The nanoparticles prepared by the present invention have near-infrared fluorescence emission, which can reduce the interference of background fluorescence and increase the signal penetration depth during the in vivo imaging process; the nanoparticles have tumor targeting properties, can be efficiently enriched in tumor tissue regions and realize precise in vivo Tumor fluorescence imaging; Nanoparticles have photodynamic properties, which can realize effective photodynamic therapy or combined photodynamic-chemotherapy for tumors. Therefore, the nanoparticles prepared by the present invention have good application prospects in the field of precise diagnosis and treatment of cancer.

Description

technical field [0001] The invention belongs to the field of biomedical technology, and specifically relates to a targeting material based on indole squaraine dye, and targeted fluorescent nanoparticles obtained through molecular self-assembly based on the indole squaraine dye, which can be used in tumor targeting therapy. Background technique [0002] Since the 20th century, the incidence of major diseases represented by cardiovascular and cerebrovascular diseases and malignant tumors has remained high. The prevention and control of major diseases is a very serious and arduous task before us. Among them, China's annual new cancer cases and deaths rank first in the world. Traditional methods of fighting cancer include surgery, chemotherapy and radiotherapy. One of the disadvantages of these methods is the poor selectivity to tumor cells, which often causes additional damage to normal cells, and cancer patients have suffered great physical and mental pain. In recent years,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/66A61K47/64A61K41/00A61K49/00A61K9/16A61P35/00A61K31/4745
CPCA61K9/1617A61K31/4745A61K41/0057A61K49/0021A61K49/0056A61K49/0093A61P35/00A61K2300/00
Inventor 尹梅贞冀辰东尹文艳
Owner BEIJING UNIV OF CHEM TECH
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