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

A kind of non-peripheral quaternary ammonium group modified zinc phthalocyanine and its preparation method and application

A technology of zinc phthalocyanine and quaternary ammonium group, which is applied in the field of non-peripheral quaternary ammonium group modified zinc phthalocyanine and its preparation. It can solve the problems of in-depth research on the structural characteristics of photosensitizers, lack of joint photosensitizers, and clinical application limitations, etc., and achieve good photodynamics. Anticancer activity, structural elucidation, efficacy in orthotopic tumor clearance

Active Publication Date: 2022-07-01
FUZHOU UNIV
View PDF9 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Hematoporphyrin derivatives have shown certain curative effects, but also exposed serious disadvantages: the maximum absorption wavelength (380-420nm) is not in the red light region (650-800nm) with better transmittance to human tissue, and the skin has high phototoxicity. It is a mixture and its composition is unstable, so its clinical application is limited, so the development of a new generation of photodynamic drugs (photosensitizers) is an international research hotspot
[0010] However, there is still a lack of effective combined photosensitizers, and no photosensitizers with high efficiency and synergy with ICB have been approved for clinical application.
There are also no reports on the combination of phthalocyanine photosensitizers and PD-L1 antibodies. In particular, the structural characteristics of photosensitizers that can be used in combination with ICB therapy to obtain highly effective synergistic anti-tumor metastasis effects have not been studied in depth, so the development of highly effective synergistic drugs with ICB The combined phthalocyanine photosensitizer has great value

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
  • A kind of non-peripheral quaternary ammonium group modified zinc phthalocyanine and its preparation method and application
  • A kind of non-peripheral quaternary ammonium group modified zinc phthalocyanine and its preparation method and application
  • A kind of non-peripheral quaternary ammonium group modified zinc phthalocyanine and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Non-peripheral quaternary ammonium group-modified zinc phthalocyanine (1-[4-(N,N,N-trimethyl-2-aminoethyl)phenoxy]zinc phthalocyanine iodide), the structure is shown in the following formula:

[0030]

[0031] Weigh 20 mg (28.5 μmol) of 1-[4-(aminoethyl)phenoxy]zinc phthalocyanine and K 2 CO 3 (168.28 μmol) was dissolved in a single-neck round-bottomed flask containing 10 ml of anhydrous DMF by sonication, cooled to 0 °C and slowly added with 2000 mg CH 3 1. After stirring for 30 min, the reaction was carried out at room temperature. TLC spot plate, stop the reaction after 24 h, spin dry the reaction solvent, dissolve the reactant with 5 ml DMF and filter with a 0.22 μm syringe filter to remove insoluble matter. The solvent was spun dry in vacuo, dissolved in 1 ml of DMF, and passed through an S-X1 gel column with DMF as the eluent, and the blue-green components at the forefront were collected. Vacuum and spin dry the solvent, dissolve it with EA and pass through ...

Embodiment 2

[0034] The target product can also be obtained by replacing the reaction solvent of Example 1 with 6 ml or 60 ml of anhydrous DMF, and other conditions remain unchanged. The structural characterization data of the product are as follows: 1 H NMR (400 MHz, DMSO) δ 9.23 (d, J = 23.3 Hz, 6H), 8.83 (s, 1H), 8.16 (s, 6H), 7.77 (d, J = 6.2 Hz, 1H), 7.44 (s, 2H), 7.37 (s, 2H), 7.09 (s, 1H), 3.90 (s, 2H), 2.74 (s, 2H), 1.50 (s, 2H), 1.26 (s, 4H),0.84 (s, 3H). HRMS (ESI) m / z calcd for C 43 H 32 N 9 OZn [M-I] + : 754.2016; found: 754.2042. HPLC (674 nm): > 95%..

Embodiment 3

[0036] 2000mg CH of Example 1 3 I, replaced with 1000mg CH 3 I or 4000mg CH 3 I, other conditions remain unchanged, the target product can also be obtained. The structural characterization data of the product are as follows: 1 H NMR (400 MHz, DMSO) δ 9.23 (d, J =23.3 Hz, 6H), 8.83 (s, 1H), 8.16 (s, 6H), 7.77 (d, J = 6.2 Hz, 1H), 7.44 (s, 2H), 7.37 (s, 2H), 7.09 (s, 1H), 3.90 (s, 2H), 2.74 (s, 2H), 1.50 (s, 2H), 1.26 (s, 4H), 0.84 (s, 3H). HRMS (ESI) m / z calcd for C 43 H 32 N 9 OZn [M-I] + : 754.2016; found: 754.2042. HPLC (674 nm): > 95%..

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 a non-peripheral quaternary ammonium group-modified zinc phthalocyanine, a preparation method and application thereof, and belongs to the field of preparation of photodynamic drugs or photosensitizers. The non-peripheral quaternary ammonium modified zinc phthalocyanine provided by the invention can be used as a photosensitizer for photodynamic therapy and photodynamic diagnosis, and can also be used for photodynamic-immune synergistic therapy. Its unique structure enables it to be used in combination with immune checkpoint blockers, has excellent synergistic anti-tumor effect, and has significant application prospects in the treatment of metastatic tumors.

Description

technical field [0001] The invention belongs to the technical field of photodynamic drugs and photosensitizers, and particularly relates to a non-peripheral quaternary ammonium group modified zinc phthalocyanine and a preparation method and application thereof. Background technique [0002] Phthalocyanine complexes are an important class of functional materials, which can be developed into functional materials for different purposes through different structural modifications. By introducing suitable substituents and central ions on the phthalocyanine ring, it is possible to develop into oxidation catalysts, desulfurization catalysts, nonlinear optical materials, photosensitizing drugs, liquid crystal materials, optical recording materials or photoconductive materials, but how to control the substituents and central ions To obtain the target functional compounds, it requires creative work. [0003] The application prospect of phthalocyanine complexes as photosensitizers in p...

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 Patents(China)
IPC IPC(8): C07D487/22A61K39/395A61K41/00A61K49/00A61P35/00
CPCC07D487/22A61K41/0071A61K39/3955A61K49/0036A61P35/00A61K2300/00A61P17/00A61K31/555C07K16/2827A61K2039/505C09B57/00
Inventor 黄剑东郑碧远柯美荣
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