Non-peripheral quaternary ammonium group modified zinc phthalocyanine as well as preparation method and application thereof

A zinc phthalocyanine, non-peripheral technology, which is applied in the field of non-peripheral quaternary ammonium group modified zinc phthalocyanine and its preparation, can solve the problems of insufficient research on the structural characteristics of photosensitizers, lack of combined photosensitizers, clinical application limitations, etc. The effect of kinetic anticancer activity, clear structure, and improved tissue penetration ability

Active Publication Date: 2020-04-28
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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

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  • Non-peripheral quaternary ammonium group modified zinc phthalocyanine as well as preparation method and application thereof
  • Non-peripheral quaternary ammonium group modified zinc phthalocyanine as well as preparation method and application thereof
  • Non-peripheral quaternary ammonium group modified zinc phthalocyanine as well as preparation method and application thereof

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-bottom flask containing 10 ml of anhydrous DMF under ultrasound, and 2000 mg CH was slowly added after cooling to 0°C 3 I. After stirring for 30 min, react 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. Vacuum and spin dry the solvent, dissolve it with 1ml DMF, pass the S-X1 gel column and use DMF as the eluent to collect the forefront blue-green components. Vacuum and spin dry the solvent, dissolve it with EA and pass it through a 100-200 mesh silica gel column (eluent is EA:DM...

Embodiment 2

[0034] The reaction solvent of Example 1 is replaced with 6ml or 60ml of anhydrous DMF, and other conditions remain unchanged, and 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%...

Embodiment 3

[0036] The 2000mg CH of Example 1 3 I, replace 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 = 23.3Hz, 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%...

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Abstract

The invention discloses non-peripheral quaternary ammonium group modified zinc phthalocyanine as well as a preparation method and application thereof, and belongs to the field of preparation of photodynamic medicines or photosensitizers. The non-peripheral quaternary ammonium group modified zinc phthalocyanine provided by the invention can be used as a photosensitizer for photodynamic therapy andphotodynamic diagnosis, and can also be used for photodynamic-immune synergistic therapy. The unique structure of the polypeptide enables the polypeptide to be combined with an immune checkpoint blocking agent for use, so that the polypeptide has an excellent synergistic anti-tumor effect and has a remarkable application prospect in treatment of metastatic tumors.

Description

Technical field [0001] The invention belongs to the technical field of photodynamic drugs and photosensitizers, and specifically 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 oxidation catalysts, desulfurization catalysts, nonlinear optical materials, photosensitive drugs, liquid crystal materials, optical recording materials or photoconductive materials, but how to control the substituents and central ions To obtain the target functional compound, it requires creative work. [0003] Phthalocyanine complexes as photosensitizers in Photodynamic Therapy (PDT) application prosp...

Claims

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Application Information

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Patent Type & Authority Applications(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
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