Amphiphilic zinc phthalocyanine and preparation method and application thereof

A zinc phthalocyanine, amphiphilic technology, applied in the field of photosensitizers, can solve the problem of unsatisfactory site specificity and achieve good singlet oxygen generation rate, high anti-tumor activity, and reduce the degree of aggregation Effect

Inactive Publication Date: 2016-04-06
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still many problems with phthalocyanine derivatives as photosensitizers, including solubility, aggregation, targeting, etc., and the specificity of the site of action has not yet achieved satisfactory results.

Method used

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  • Amphiphilic zinc phthalocyanine and preparation method and application thereof
  • Amphiphilic zinc phthalocyanine and preparation method and application thereof
  • Amphiphilic zinc phthalocyanine and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] A preparation method of an amphiphilic zinc phthalocyanine photosensitizer, the steps are as follows:

[0042] (1) Under nitrogen protection, 4-nitrophthalonitrile, p-hydroxybenzylamine and K 2 CO 3 Add it into the reaction flask at a molar ratio of 1:1.5:2, use 10ml of anhydrous DMF as a solvent, and react at 40-50°C for 5h to obtain phthalonitrile intermediate 1.

[0043] (2) Under the protection of nitrogen, the phthalonitrile intermediate 1 was stirred and dissolved in absolute ethanol, and mixed with 1,3-propane sultone at a molar ratio of 1:1.3 at room temperature for 1 hour, and then heated to 80 After reacting at ℃ for 6 hours, 15 ml of acetone was added to continue stirring for 3 hours, and the phthalonitrile intermediate 2 was obtained by filtration.

[0044] (3) Under the protection of nitrogen, phthalonitrile intermediate 2, zinc acetate and DBU were added to n-pentanol in a molar ratio of 4:2.5:2.5, refluxed for 24 hours, and poured into acetone after coo...

Embodiment 2

[0047] A preparation method of an amphiphilic zinc phthalocyanine photosensitizer, the steps are as follows:

[0048] (1) Under nitrogen protection, 4-nitrophthalonitrile, p-hydroxybenzylamine and K 2 CO 3 Add it into the reaction flask at a molar ratio of 1:1:1.5, use 10ml of anhydrous DMF as a solvent, and react at 50-60°C for 5h to obtain phthalonitrile intermediate 1.

[0049] (2) Under the protection of nitrogen, the phthalonitrile intermediate 1 was stirred and dissolved in absolute ethanol, and mixed with 1,3-propane sultone at a molar ratio of 1:1.1 at room temperature for 1 hour, and then heated to 80 After reacting at ℃ for 6 hours, 15 ml of acetone was added to continue stirring for 3 hours, and the phthalonitrile intermediate 2 was obtained by filtration.

[0050] (3) Under the protection of nitrogen, phthalonitrile intermediate 2, zinc acetate and DBU were added to n-pentanol in a molar ratio of 4:2.5:2.5, refluxed for 24 hours, and poured into acetone after cooli...

Embodiment 3

[0052] The amphiphilic zinc phthalocyanine and hematoporphyrin aqueous solution containing ADPA were irradiated with 665nm LED lamp respectively, and by detecting its ultraviolet-visible absorption spectrum, it can be found that with the prolongation of the illumination time, the characteristic of ADPA in the two solutions is located at 378nm. The peak intensity of the absorption peak is continuously decreasing, and the relationship curve of the decline value of the characteristic absorption peak of ADPA at 378nm is obtained as the light time changes. By comparison, it is found that the singlet oxygen production rate of the amphiphilic zinc phthalocyanine is higher than that of hematoporin phylloline.

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Abstract

The present invention discloses an amphiphilic zinc phthalocyanine and preparation method and application thereof in the photodynamic therapy. The amphiphilic zinc phthalocyanine (structural formula shown as below) is simple for preparation, has high anti-tumor activity and interaction with calf thymus DNA, and can effectively break the calf thymus DNA. Therefore, the amphiphilic zinc phthalocyanine hasy with good application prospects in photodynamic therapy.

Description

technical field [0001] The invention belongs to the technical field of photosensitizers with photodynamic activity, relates to a phthalocyanine and its preparation and application, in particular to a novel amphiphilic zinc phthalocyanine 2(3), 9(10), 16(17) , 23(24)-Tetrakis-(((2-aminopropane-1-sulfonic acid)methyl)phenoxy)zinc(II)phthalocyanine, and its preparation and use. Background technique [0002] Photodynamic therapy (PDT for short) is a new disease treatment method based on the interaction of light, photosensitizer and oxygen, which has developed rapidly in recent years. PDT is mainly used in the diagnosis and treatment of malignant tumors. At present, there are many examples of PDT applied to the treatment of skin cancer, lung cancer, esophageal cancer, bladder cancer, etc., and it is also used in the treatment of some non-tumor diseases, such as genital warts, psoriasis, etc. There are also good applications. Compared with traditional surgery, chemotherapy, radi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K41/00A61P35/00
CPCC07D487/22A61K41/0071
Inventor 魏少华袁林新周林周家宏林云姜巍巍
Owner NANJING NORMAL UNIVERSITY
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