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A kind of phthalocyanine metal complex and its preparation method and application

A metal complex, phthalocyanine technology, applied in the field of phthalocyanine metal complex and its preparation, can solve the problems of unstable mixture composition, low dark toxicity, easy aggregation, etc., achieve high singlet oxygen quantum yield, improve light Kinetic activity, the effect of large molar absorption coefficient

Active Publication Date: 2017-01-18
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 shortcomings: the maximum absorption wavelength (380-420nm) is not in the red light region (650-800nm) with better transmittance to human tissue, and the skin is phototoxic. And the composition of the mixture is unstable, so its clinical application is limited
[0006]Phthalocyanine metal complexes have the characteristics of the maximum absorption wavelength in the red light region that is easy to pass through human tissue, and low dark toxicity, but the currently reported biologically active Phthalocyanine complexes still have deficiencies, such as easy aggregation in water, or complex synthetic routes, or poor bioselectivity, etc., which need further improvement

Method used

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  • A kind of phthalocyanine metal complex and its preparation method and application
  • A kind of phthalocyanine metal complex and its preparation method and application
  • A kind of phthalocyanine metal complex and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0041] 1(4), 8(11), 15(18), 22(25)-tetrakis[2,4,6-tris(N,N-dimethylaminomethyl)-phenoxy]zinc phthalocyanine, Or the synthesis of four-alpha-[2,4,6-tri(N,N-dimethylaminomethyl)-phenoxy]zinc phthalocyanine comprises the following steps:

[0042] 1) With 25mmol 3-nitrophthalonitrile and 13.5mmol 2,4,6-tris(dimethylaminomethyl)-phenol as reactants, 50mL N-N-dimethylformamide as solvent A, separate After three batches of 50mmol potassium carbonate were added, under the protection of nitrogen, the reaction was stirred at 45°C for 24 hours, and monitored by thin-layer chromatography. When the 3-nitrophthalonitrile was consumed, the reaction was terminated, the reaction mixture was suction filtered, and the filtrate was collected. , evaporate the solvent to dryness, dissolve the solid with hydrochloric acid aqueous solution, remove the insolubles by suction filtration, add sodium hydroxide to the filtrate, let stand after a large amount of precipitation, suction filtration, wash the f...

Embodiment 2

[0052] 1,8(11),15(18),22(25)-tetrakis[2,4,6-tris(N,N,N-trimethylammoniomethyl)-phenoxy]phthalocyanine zinc dodecaiodide Salt, or the synthesis of four-alpha-[2,4,6-three (N,N,N-trimethylammonium methyl)-phenoxy] phthalocyanine zinc dodecaiodide salt, comprises the following steps:

[0053] 1) Prepare zinc tetrakis-α-(2,4,6-tris(N,N-dimethylaminomethyl)-phenoxy)phthalocyanine according to the method described in Example 1;

[0054] 2) Add 0.035mmol tetrakis-α-[2,4,6-tris(N,N-dimethylaminomethyl)-phenoxy]zinc phthalocyanine and 7.9mmol methyl iodide to 15mL chloroform, Stir and react at 25°C for 30 hours. After the reaction, filter with suction, rinse the filter cake with chloroform, and dry the obtained solid in vacuum to obtain 107 mg of the blue target product with a yield of 91.8%. Its structural formula is as follows:

[0055] .

[0056] The characterization data of product are as follows: IR (KBr, cm -1 ): 3010 (Ar-H); 2951, 2858 (CH 3 , CH 2 ); 1614, 1468 (benzene,...

Embodiment 3

[0060]The product tetrakis-α-[2,4,6-tri(N,N-dimethylaminomethyl)-phenoxy]zinc phthalocyanine obtained in Example 1 and the product tetrakis-α-[2, 4,6-tris(N,N,N-trimethylammoniomethyl)-phenoxy]phthalocyanine zinc dodecaiodide salt wavelength scan in the range of 300-800nm, and the concentration-absorption value of each complex See the relationship diagram respectively figure 1 and figure 2 , the solvents used for the two complexes are N-N-dimethylformamide and water, respectively.

[0061] It can be seen from the figure that the zinc tetra-α-[2,4,6-tri(N,N-dimethylaminomethyl)-phenoxy]phthalocyanine has the largest The absorption wavelength is 700nm, and the molar absorptivity is 2.60×10 5 (M -1 cm -1 ); the maximum absorption wavelength of four-α-[2,4,6-tri(N,N,N-trimethylammoniomethyl)-phenoxy]phthalocyanine zinc dodecaiodide salt in water is 694nm, and the concentration It has a linear relationship with the absorption value, and the molar absorptivity is 2.52×10 5 (...

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Abstract

The invention discloses a phthalocyanine metal complex as well as a preparation method and an application of the phthalocyanine metal complex. 3-[2,4,6-tri(dimethylamino methyl)-phenoxyl] phthalonitrile is prepared by using 2-phthalonitrile nitryl and 2,4,6-tri(dimethylamino methyl)-phenol as reactants, and further, the phthalocyanine metal complex substituted with amido or amido alpha bit is prepared. The phthalocyanine metal complex has the characteristics of high photosensitive activity and high water solubility; the phthalocyanine metal complex exists in water in a monomer mode, so that the photodynamic activity is facilitated in the water; the phthalocyanine metal complex is subjected to absorption spectroscopic redshift and shifted to a near-infrared area where is beneficial for penetrating through human tissues. The phthalocyanine metal complex is specially high in photodynamic antifungal activity and can be used for preparing photosensitizers or photodynamic medicines or photosensitive medicaments.

Description

technical field [0001] The invention belongs to the field of preparation of photodynamic drugs or photosensitizers, and in particular relates to a phthalocyanine metal complex containing an amino group or an ammonium substituent group and a preparation method and application thereof. Background technique [0002] Photodynamic therapy (or photodynamic therapy) is essentially the application of photosensitization reactions of photosensitizers (or photosensitizers) in the medical field. Its action process is to inject the photosensitizer into the body first, and after a period of time (after the drug is relatively enriched in the target body), the target body is irradiated with light of a specific wavelength (for the target in the body cavity, the light source can be introduced with the help of optical fiber and other interventional technologies. ), the photosensitizer enriched in the target body, under light excitation, inspires a series of photophysical and photochemical reac...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K31/409A61K41/00A61K49/00A61P35/00A61P35/02A61P31/10A01N43/90A01P1/00
CPCA61K41/0071C07D487/22
Inventor 黄剑东李兴淑柯美荣
Owner FUZHOU UNIV
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