Arginine-substituted phthalocyanine derivatives, and synthesis method and application thereof

A technology of phthalocyanine derivatives and arginine, which is applied in the field of photosensitizers, can solve the problems of no targeting of tumor cells and no specific targeting of tumor tissues, and achieve inhibition of adhesion and proliferation, good application prospects, and dark toxicity low effect

Active Publication Date: 2016-11-09
NANJING NORMAL UNIVERSITY
View PDF2 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, generally positively charged phthalocyanines are in the form of quaternary ammonium salts, and the preparation process requires the use of highly toxic methylating reagents (such as methyl iodide), and the prepared quaternary ammonium phthalocyanines have no target for tumor cells. sex
Protonated am

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
  • Arginine-substituted phthalocyanine derivatives, and synthesis method and application thereof
  • Arginine-substituted phthalocyanine derivatives, and synthesis method and application thereof
  • Arginine-substituted phthalocyanine derivatives, and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] (1) Under the protection of nitrogen, 4-nitrophthalonitrile, 4-hydroxybenzoic acid and basic catalyst are stirred and reacted at a molar ratio of 1:1:2, and DMF is used as a solvent, and the reaction is carried out at 40°C for 6 hours to obtain ortho Phthalonitrile intermediate 1;

[0043] (2) Under nitrogen protection, with n-amyl alcohol as solvent, Zn(OAc) 2 , The molar ratio of phthalonitrile intermediate 1 to DBU is 1:2:3; the reaction temperature is 120°C-140°C, the reaction time is 24h, the reaction solution is cooled to room temperature, and the solvent is distilled off under reduced pressure. The solid was dissolved with KOH aqueous solution, treated under reflux for 6 h and then cooled to room temperature. The filter cake was collected by filtration. The filter cake was dissolved with alkali again, and the insoluble part was removed by filtration. The pH of the filtrate was adjusted to be acidic to precipitate the product. The solid was collected after rep...

Embodiment 2

[0047] (1) Under the protection of nitrogen, 4-nitrophthalonitrile, 4-hydroxybenzoic acid and basic catalyst are stirred and reacted in a molar ratio of 1:3:4, and DMF is used as a solvent, and the reaction is carried out at 40°C for 6h to obtain ortho Phthalonitrile intermediate 1;

[0048] (2) Under the protection of nitrogen, with n-amyl alcohol as solvent, Cu(Ac) 2 , The molar ratio of phthalonitrile intermediate 1 to DBU is 1:2:4; the reaction temperature is 120°C-140°C, the reaction time is 24h, the reaction solution is cooled to room temperature, and the solvent is distilled off under reduced pressure. The solid was dissolved with KOH aqueous solution, treated under reflux for 6 h and then cooled to room temperature. The filter cake was collected by filtration. The filter cake was dissolved with alkali again, and the insoluble part was removed by filtration. The pH of the filtrate was adjusted to be acidic to precipitate the product. The solid was collected after re...

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

No PUM Login to view more

Abstract

The invention discloses arginine-substituted phthalocyanine derivatives and a synthesis method thereof, and application of the arginine-substituted phthalocyanine derivatives in photodynamic therapeutics. The structure of the arginine-substituted phthalocyanine derivatives is disclosed as the following formula in the specification. The synthesis method of the arginine-substituted phthalocyanine derivatives is simple, and does not need any toxic methylation reagent; and the arginine-substituted phthalocyanine derivatives are positively charged under physiological conditions, have the advantages of high active oxygen generation capacity, favorable photosensitive antineoplastic activity and low dark toxicity, and thus, have favorable application prospects in photodynamic therapeutics.

Description

technical field [0001] The invention belongs to the technical field of photosensitizers with photodynamic activity, and relates to a phthalocyanine derivative, in particular to an arginine-substituted phthalocyanine derivative, its synthesis method and its application in photodynamic therapy. Background technique [0002] Photodynamic therapy (PDT), also known as photosensitive therapy and photochemotherapy, is a new method developed in recent years to treat tumors with photochemical reactions. The treatment process is as follows: the photosensitizer is injected into the patient's body, transmitted through the blood, and after a period of metabolism, the photosensitizer is selectively retained in the diseased tissue. Then, the lesion tissue is irradiated with light that matches the wavelength of the photosensitizer, and the photosensitizer undergoes a photodynamic reaction with the participation of oxygen, thereby exerting curative effect and finally killing tumor cells. PD...

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
IPC IPC(8): C07D487/22A61K41/00A61P35/00
CPCA61K41/0076C07D487/22
Inventor 魏少华周蓉蓉王傲周林周家宏
Owner NANJING NORMAL UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap