Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Phthalocyanine-artemisinin conjugate used as sonodynamic/photodynamic sensitizer as well as preparation method and application of phthalocyanine-artemisinin conjugate

A conjugate, artemisinin technology, applied in chemical instruments and methods, compounds of Group 4/14 elements of the periodic table, medical preparations of inactive ingredients, etc. Dynamic therapy needs to be improved to achieve good anti-tumor effect, excellent synergistic anti-tumor, and excellent tumor targeting effect

Active Publication Date: 2021-12-14
FUZHOU UNIV
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, organic sonosensitizers mainly come from photosensitizers, such as hematoporphyrin monomethyl ether (HMME), protoporphyrin IX (PpIX), chloroporphyrin e6 (Ce6), porphyrin sodium (DVDMS), phthalocyanine, etc. , but the sonosensitization effect of these photosensitizers needs to be improved, and the sonodynamic therapy itself needs to be improved

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Phthalocyanine-artemisinin conjugate used as sonodynamic/photodynamic sensitizer as well as preparation method and application of phthalocyanine-artemisinin conjugate
  • Phthalocyanine-artemisinin conjugate used as sonodynamic/photodynamic sensitizer as well as preparation method and application of phthalocyanine-artemisinin conjugate
  • Phthalocyanine-artemisinin conjugate used as sonodynamic/photodynamic sensitizer as well as preparation method and application of phthalocyanine-artemisinin conjugate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] (1) 3-(2-(2-hydroxyethoxy)ethoxy)ethoxyphthalonitrile ( )Synthesis:

[0043] Add (5~50 mmol, 10 mmol in this example) triethylene glycol and potassium carbonate (10~40 mmol, 20 mmol in this example) into DMF (10~50 mL, 35 mL in this example), Stir for 10 minutes (under the protection of nitrogen, slow down the flow rate and stirring speed), then add 3-nitrophthalonitrile (5 mmol), and stir at room temperature for 12 h under the protection of nitrogen. TLC detection reflected the situation. After the reaction was completed, the reaction solution was concentrated by rotary evaporation, and the concentrated solution was added to ice water to precipitate a light yellow solid. The filter cake was collected by suction filtration with a Buchner funnel and dried in a vacuum oven to obtain a solid product. The yield was 54.35%.

[0044] Characterization data: 1 H NMR (400 MHz, CDCl 3 ) δ 7.66 (t, J = 8.2 Hz, 1H), 7.38 (d, J = 7.7 Hz, 1H), 7.32 (d, J = 8.7 Hz, 1H), 4.41...

Embodiment 2

[0049] (1) 3-(2-hydroxyethoxy)ethylmercaptophthalonitrile ( )Synthesis:

[0050] Add (5~50 mmol, 10 mmol in this example) 2-mercaptoethoxyethanol and potassium carbonate (10~40 mmol, 20 mmol in this example) to DMF (10~50 mL, choose in this example 35mL), stirred for 10 minutes (nitrogen protection, slow flow and stirring speed), then added 3-nitrophthalonitrile (5mmol), stirred at room temperature for 12-24h under nitrogen protection. TLC detection reflected the situation. After the reaction was completed, the reaction solution was concentrated by rotary evaporation, and the concentrated solution was added to ice water to precipitate a yellow solid. The filter cake was collected by suction filtration with a Buchner funnel and dried in a vacuum oven to obtain a solid product. The yield was 86.65%.

[0051] Characterization data: 1 H NMR (400 MHz, DMSO- d 6) δ 7.74 (dd, J = 7.6, 1.3 Hz, 1H),7.65-7.57 (m, 2H), 3.78 (t, J = 6.2 Hz, 2H), 3.73-3.70 (m, 2H), 3.61-3.57 (m,2H)...

Embodiment 3

[0056] (1) 3,6-bis-(2-(2-hydroxyethoxy)ethoxy)ethoxyphthalonitrile ( )Synthesis:

[0057] Measure triethylene glycol (100~300 mmol, choose 180 mmol in this example), triethylamine (2~10 mL, choose 5 mL in this example) 20 mL for the example) and stirred at 0°C for 20 min; weigh p-toluenesulfonyl chloride (30 mmol) plus dichloromethane (5~30 mL, 20 mL for this example) ) dissolved, slowly added to the constant pressure dropping funnel (keep 0 °C reaction conditions), after the dropwise addition, the temperature of the system was slowly raised to room temperature, and the reaction was continued for 12-48 hours with stirring, preferably 18 hours. Stop the reaction, wash with water, extract with DCM three times, collect the organic phase, add anhydrous sodium sulfate to dry, filter sodium sulfate, and rotary evaporate to dry to obtain the product. After further purification with silica gel (ethyl acetate:dichloromethane=8:2), the target product was collected and concentrated by...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
particle diameteraaaaaaaaaa
Login to View More

Abstract

The invention discloses a phthalocyanine-artemisinin conjugate used as a sonodynamic / photodynamic sensitizer as well as a preparation method and application of the phthalocyanine-artemisinin conjugate. The phthalocyanine-artemisinin can be self-assembled in water. In water, the conjugate efficiently generates active oxygen under an ultrasonic action, and can be used as a sonosensitizer. Meanwhile, the conjugate and the self-assembly thereof can generate active oxygen under the action of light, and can also be used as a photosensitizer. The phthalocyanine-artemisinin conjugate obtained by the invention can generate an effective sonodynamic therapy anti-tumor effect, also has a remarkable sonodynamic and photodynamic synergistic anti-tumor effect, and has a remarkable application prospect in the aspect of preparing sonodynamic therapy and sonodynamic / photodynamic synergistic therapy drugs.

Description

technical field [0001] The invention belongs to the field of functional materials and medicines, and in particular relates to a phthalocyanine-artemisinin conjugate used as a sonodynamic / photodynamic sensitizer, a preparation method and application thereof. Background technique [0002] Derived from photodynamic therapy (PDT), sonodynamic therapy (SDT) has emerged as a novel non-invasive cancer treatment modality that uses low-intensity ultrasound instead of light used in PDT as an excitation source to induce the activation of sonosensitizers , generate reactive oxygen species (ROS), causing damage to cancer cells and tumor tissues. In addition to being non-invasive and specific targeting selectivity like PDT, SDT also benefits from the high penetration depth of ultrasound into tissues, which can directly reach and Treat deep tumor tissue, and treatment depth is one of the Achilles' heels of PDT. [0003] The therapeutic effect of SDT largely depends on the performance of s...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C07F7/10A61K41/00A61K47/55A61K31/357A61P35/00
CPCC07D519/00C07F7/10A61K41/0076A61K47/55A61K41/0033A61K31/357A61P35/00A61K2300/00
Inventor 黄剑东柯美荣赵鹏辉郑碧远
Owner FUZHOU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com