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Targeting material based on indolium squarine dye, preparation method thereof, fluorescent nano-particle, and preparation method of fluorescent nano-particle

An indole squaraine, fluorescent nanotechnology, applied in the field of biomedicine, can solve the problems of weak application in the field of cancer photodiagnosis, lack of specific tumor targeting ability and cancer treatment ability, etc., and achieves good product stability, biological The effect of high safety and high tumor inhibition rate

Active Publication Date: 2018-12-18
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Targeting material based on indolium squarine dye, preparation method thereof, fluorescent nano-particle, and preparation method of fluorescent nano-particle
  • Targeting material based on indolium squarine dye, preparation method thereof, fluorescent nano-particle, and preparation method of fluorescent nano-particle
  • Targeting material based on indolium squarine dye, preparation method thereof, fluorescent nano-particle, and preparation method of fluorescent nano-particle

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 human liver cancer in vitro cell (BEL-7402) tumor model of 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, and 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 sacrific...

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Abstract

The invention provides a targeting material based on an indolium squarine dye, a preparation method thereof, a fluorescent nano-particle, and a preparation method of the fluorescent nano-particle. Bromine, hydrogen or methyl-substituted indolium squarine is coupled with targeting polypeptide RGD molecules or is respectively coupled with RDG molecules and an anticancer drug camptothecin to obtain amphiphilic diagnosis and treatment molecules. The molecules can be self-assembled in water to form the stable nano-particle with a uniform size. The nano-particle prepared in the invention can emit near infrared fluorescence, and can reduce the interference of background fluorescence and increase the signal penetrating depth in an in-vivo imaging process; the nano-particle has a tumor targeting performance, can be efficiently enriched in a tumor tissue are and can realize accurate in-vivo tumor fluorescence imaging; and the nano-particle has photodynamic properties, and can achieve effective photodynamic therapy or photodynamic therapy-chemotherapy combined therapy for tumors. So the nano-particle prepared in the invention has a good application prospect in the field of accurate diagnosisand treatment of cancers.

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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IPC IPC(8): A61K41/00A61K49/00A61K47/64A61K9/16A61P35/00A61K31/4745
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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