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Medical photosensitizer and preparation method thereof

A technology of photosensitizer and photodynamic therapy, which is applied in the direction of medical preparations containing active ingredients, pharmaceutical formulas, wave energy or particle radiation treatment materials, etc. It can solve the problem of weakening photodynamic killing of tumor cells and poor stability of metal phthalocyanine photosensitizers , Intermolecular easy polymerization and other problems, to achieve the effect of less isomers, easy purification and separation, and good product solubility

Inactive Publication Date: 2011-07-27
FUJIAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the metal phthalocyanine photosensitizer after sulfonation is poor in stability and easy to polymerize between molecules, which weakens the ability of photodynamic killing of tumor cells, and the product is a mixture of different degrees of sulfonation, which is difficult to separate and needs to be separated by a high-performance liquid phase preparative column. Purification, these defects limit the development and clinical application of such complexes

Method used

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  • Medical photosensitizer and preparation method thereof
  • Medical photosensitizer and preparation method thereof
  • Medical photosensitizer and preparation method thereof

Examples

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Embodiment 1

[0034] (1) Synthesis of 4-trifluoroethaneoxyphthalonitrile

[0035]

[0036] Add 40mmol of 4-nitrophthalonitrile and 240ml of dry dimethyl sulfoxide (DMSO) and 40mmol of trifluoroethanol to CaCl 2 In the three-necked flask of the drying tube, keep 25°C for stirring reaction, add 2.4g of lithium hydroxide in 3 batches within 2h, (in the actual test operation, preferably add 0.8g of lithium hydroxide every 40 minutes). After reacting for 72 hours, it was slowly dropped into deionized water to obtain a turbid liquid, which was put into the refrigerator and taken out after freezing. After standing for a period of time, filter, wash with deionized water until neutral, and filter with suction to obtain a solid. Recrystallization from methanol afforded a purified intermediate of 4-trifluoroethaneoxyphthalonitrile. Yield 81%. Measure the infrared spectrogram of 4-trifluoroethaneoxy phthalonitrile, IR (cm -1 ): 3075(Ar, H), 2230(C≡H), 1920, 1590, 1485, 1450, 1420, 1400(C-F), 132...

Embodiment 2

[0047] (1) In vitro photodynamic therapy test

[0048] Preparation of tetrakis-(trifluoroethoxy)zinc phthalocyanine (ZnPcF) emulsion: (a) ZnPcF (67.85 mg) was first dissolved in ethanol (2 mL). The ethanol solution was slowly added to Pluronic F68 (Pluronic F68, F68) aqueous solution (10%, 50mL) while vigorously stirring, and the concentration of ZnPcF in the final solution was 1.3mg·mL -1 (1.34mmol·L -1 ), the concentration of F68 was 9.6% (w / v). (b) At the same time, 2 mL of ethanol was added to F68 aqueous solution (50 mL) as a solvent control solution. The above solution was sterilized by filtration through a 0.45 μm filter membrane and stored in a refrigerator in the dark. F68 refers to Pronic F68.

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Abstract

The invention discloses a medical photosensitizer and a preparation method thereof. The photosensitizer is tetra(trifluoroethoxy) phthalocyaninate. The preparation method comprises: synthesizing an intermediate 4-trifluoroethoxybenzenedicarbonitrile by reacting 4-nitro-2-benzenedicarbonitrile with trifluoroethanol in dry dimethyl sulfoxide (DMSO) in the presence of lithium hydroxide; and reacting the intermediate and anhydrous metal chloride in dry n-amyl alcohol in the presence of 1,8-diazabicyclo[5,4,0]-undec-7-ene (DBU) which is a strong organic alkali to obtain the tetra(trifluoroethoxy) phthalocyaninate. In the method, the conditions are mild, the reaction temperature is only about 70 DEG C, and the yield is up to 78 percent. In-vitro cell experiments prove that the tetra(trifluoroethoxy) phthalocyaninate has high ability of killing HL-60 and SW-1116 cells. The results of in-vivo photodynamic therapy (PDT) tests show that ZnPcF has PDT effect on U14 transplantable tumor in mice and that the U14 transplantable tumor inhibition rate of the ZnPcF reaches 79.1 percent.

Description

technical field [0001] The invention relates to a medical photosensitizer and a preparation method thereof. The photosensitizer can be used as a medicine for photodynamic therapy of tumors. Background technique [0002] According to the report of the World Health Organization, 9 million new cases of cancer occur every year in the world, and 5 million people die of cancer. Cancer has replaced cardiovascular and cerebrovascular diseases as the number one killer threatening human life. Tumors, especially malignant tumors, are one of the main problems that mankind expects to overcome in the 21st century. Therefore, the study of tumor prevention drugs has become one of the research hotspots in oncology and pharmacy at home and abroad. [0003] Photodynamic therapy (PDT for short) is a new therapy that began to be used clinically in the late 1970s. Photodynamic therapy, also known as photoradiation therapy (Photoradiation Therapy) or photochemotherapy (Photochemotherapy) [1，2] ...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K41/00A61K31/409A61P35/00A61P35/02
Inventor 黄丽英吴晓珊罗红斌林新华王勇
Owner FUJIAN MEDICAL UNIV
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