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Ph-sensitive axially substituted silicon phthalocyanine complexes and their preparation methods and applications in medicine

A technology of dichlorosilicon phthalocyanine and compound, which is applied in the field of medicine and can solve the problems of incapable of photodynamic damage, complex components, and weak targeting effect

Active Publication Date: 2017-12-15
SHENZHEN DAWU TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although Porfemna and Xipofen have achieved clinical success, their components are complex, and their roles in photodynamic damage have not yet been clarified. The inactive components accounting for more than 20% of the total amount of the drug are not It cannot produce effective photodynamic damage to the diseased target tissue, but becomes the culprit that causes photosensitivity in normal tissue
In addition, the first generation of photosensitizing drugs do not have a strong tumor-targeting effect, and research on efficient, low-toxic photosensitizing drugs with tumor-targeting properties is a recent research hotspot.

Method used

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  • Ph-sensitive axially substituted silicon phthalocyanine complexes and their preparation methods and applications in medicine
  • Ph-sensitive axially substituted silicon phthalocyanine complexes and their preparation methods and applications in medicine
  • Ph-sensitive axially substituted silicon phthalocyanine complexes and their preparation methods and applications in medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] The synthesis of embodiment 1 compound 1

[0067]

[0068] step 1

[0069] In an ice-water bath, compound 1-1 (1.62g, 10mmol), cholesterol chloroformate (2.2g, 4.9mmol) and triethylamine (2g, 20mmol) were added into dichloromethane (30mL), and the stirring reaction was continued for 3 hours. Stop the reaction, add water (200mL) to the reaction solution, stir and let it stand, collect the organic phase, dry the organic phase with anhydrous sodium sulfate, and distill under reduced pressure. The crude product is separated and purified by silica gel chromatography column, and the eluent is trichloro Methane / methanol (9:1) afforded 1-2 as a white solid (1.45 g, 51%). MS(ESI):m / z=598[M+Na] + .

[0070] step 2

[0071] In an ice-water bath, add compound 1-2 (1.2g, 2.1mmol), compound 1-3 (0.52g, 1.5mmol), pyridine (1.1g, 14mmol) into dichloromethane (35mL), withdraw from the ice-water bath, The temperature was raised to room temperature and the stirring reaction was co...

Embodiment 2

[0074] The synthesis of embodiment 2 compound 2

[0075]

[0076] step 1

[0077] In an ice-water bath, add compound 2-1 (0.57g, 3.5mmol), cholesterol chloroformate (1.55g, 3.5mmol) and pyridine (0.8g, 10.1mmol) into dichloromethane (35mL), and the temperature was raised to room temperature, Continue to stir the reaction for 2 hours, stop the reaction, add water (100mL) to the reaction solution, stir and let it stand, collect the organic phase, dry the organic phase with anhydrous sodium sulfate, and distill under reduced pressure. The crude product is separated and purified by silica gel chromatography. The eluent was chloroform / methanol (15:1) to obtain white solid 2-2 (0.92 g, 46%). MS(ESI):m / z=599[M+Na] + .

[0078] step 2

[0079] In an ice-water bath, add compound 2-2 (0.9g, 1.6mmol), compound 2-3 (0.9g, 3.0mmol) into tetrahydrofuran (30mL), and slowly add sodium hydride (0.3g, 12.5mmol) into the reaction solution ), the ice-water bath was withdrawn, the temperat...

Embodiment 3

[0082] The synthesis of embodiment 3 compound 3

[0083]

[0084] step 1

[0085] In an ice-water bath, add compound 1-2 (1.2g, 2.1mmol), compound 3-1 (0.5g, 2.4mmol), pyridine (0.8g, 10.1mmol) into dichloromethane (25mL), and the temperature was raised to room temperature Continue to stir the reaction for 8 hours, stop the reaction, add water (100mL) to the reaction solution, stir and let it stand, collect the organic phase, dry the organic phase with anhydrous sodium sulfate, and distill under reduced pressure. The crude product is separated and purified by silica gel chromatography. The eluent was chloroform / methanol (9:1) to obtain pale yellow oil 3-2 (0.85g, 62%). MS(ESI):m / z=663[M] + . step 2

[0086] Dichlorosilicon phthalocyanine (0.21g, 0.34mmol), compound 1-4 (1.5g, 2.2mmol) and pyridine (1g, 12.7mmol) were added to toluene (30mL), and the temperature was raised to 120°C for 24 hours. Evaporate the solvent under pressure, add 100 ml of chloroform and 100 ml o...

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Abstract

The present invention relates to a pH-sensitive ketal-linked cholesterol-silicon phthalocyanine complex, a preparation method therefor and medical application thereof, and in particular, to a silicon phthalocyanine complex represented by a general formula (I), a preparation method therefor, a pharmaceutical composition containing the complex, and use thereof as a photosensitizer, especially use in treating cancers, wherein substituents in the general formula (I) have the same definitions as those in the description. Due to the presence of cholesterol groups, the series of complexes are hardly taken by tumor cells and normal cells; however, in a tumor tissue cell external subacid environment, ketal linkage undergoes hydrolysis reaction, and hydrolysis derivatives of silicon phthalocyanine can be easily taken by cancer cells, show extremely high photosensitivity, and can be prepared into tumor cell external subacid environment targeted photosensitive drug.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to a silicon phthalocyanine complex and a preparation method thereof and its application in medicine. The invention discloses its use as a photosensitizer for treating cancer. technical background [0002] Photodynamic therapy (PDT for short), also known as photoradiation therapy (PRT for short) or photochemotherapy (Photochemotherapy), is a treatment method based on the photochemical reaction principle of specific chemical substances. The chemical substances used are called tumor chemotherapeutic drugs (also known as photosensitizer, Photosensitizer, PS for short). The process of PDT therapy is to inject the photosensitizer into the body through intravenous injection (for the skin, it can also be applied to the affected area), and after a certain period of time, the tumor tissue is irradiated with light of a specific wavelength, and the photosensitizer enriched in the tumor tissue is stimulat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/02A61K41/00A61K31/695A61P35/00
CPCA61K41/0071C07F7/025
Inventor 蒋雄杰黄华静
Owner SHENZHEN DAWU TECH CO LTD