pH sensitive axially substituted silicon phthalocyanine complex, preparing method of pH sensitive axially substituted silicon phthalocyanine complex and application of pH sensitive axially substituted silicon phthalocyanine complex to medicines

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, weak targeting effect, complex components, etc.

Active Publication Date: 2017-04-19
SHENZHEN SONO PHOTODYNAMIC BIO MED TECH LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] 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 complex, preparing method of pH sensitive axially substituted silicon phthalocyanine complex and application of pH sensitive axially substituted silicon phthalocyanine complex to medicines
  • pH sensitive axially substituted silicon phthalocyanine complex, preparing method of pH sensitive axially substituted silicon phthalocyanine complex and application of pH sensitive axially substituted silicon phthalocyanine complex to medicines
  • pH sensitive axially substituted silicon phthalocyanine complex, preparing method of pH sensitive axially substituted silicon phthalocyanine complex and application of pH sensitive axially substituted silicon phthalocyanine complex to medicines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1 Synthesis of Compound 1

[0068]

[0069] step 1

[0070] In an ice-water bath, add compound 1-1 (1.62g, 10mmol), cholesterol chloroformate (2.2g, 4.9mmol) and triethylamine (2g, 20mmol) into dichloromethane (30mL), continue to stir and react for 3 hours, Stop the reaction, add water (200 mL) to the reaction solution, stir and 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 a silica gel column. The eluent is trichloro Methane / methanol (9:1) to obtain 1-2 as a white solid (1.45 g, 51%). MS(ESI): m / z=598[M+Na] + .

[0071] Step 2

[0072] 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), remove the ice-water bath, The temperature was raised to room temperature and the reaction was continued with stirring for 6 hours. The reaction was stopped. Water (100mL) wa...

Embodiment 2

[0075] Example 2 Synthesis of Compound 2

[0076]

[0077] step 1

[0078] 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), the temperature is raised to room temperature, Continue to stir the reaction for 2 hours, stop the reaction, add water (100mL) to the reaction solution, stir and stand, collect the organic phase, dry the organic phase with anhydrous sodium sulfate, distill under reduced pressure, and separate and purify the crude product with silica gel chromatography. The eluent was chloroform / methanol (15:1) to obtain 2-2 (0.92 g, 46%) as a white solid. MS(ESI): m / z=599[M+Na] + .

[0079] Step 2

[0080] In an ice-water bath, add compound 2-2 (0.9g, 1.6mmol), compound 2-3 (0.9g, 3.0mmol) to tetrahydrofuran (30mL), and slowly add sodium hydride (0.3g, 12.5mmol) to the reaction solution ), remove the ice-water bath, raise the temperature to room temperature and continu...

Embodiment 3

[0083] Example 3 Synthesis of Compound 3

[0084]

[0085] step 1

[0086] 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 raise the temperature to room temperature Continue to stir the reaction for 8 hours, stop the reaction, add water (100mL) to the reaction solution, stir and stand, collect the organic phase, dry the organic phase with anhydrous sodium sulfate, distill under reduced pressure, and separate and purify the crude product with a silica gel chromatography column. The eluent was chloroform / methanol (9:1) to obtain a pale yellow oil 3-2 (0.85 g, 62%). MS(ESI): m / z=663[M] + . Step 2

[0087] Dichlorosilicon phthalocyanine (0.21g, 0.34mmol), compound 1-4 (1.5g, 2.2mmol) and pyridine (1g, 12.7mmol) were added to toluene (30mL), the temperature was raised to 120℃ and reacted for 24 hours. The solvent was distilled off by pressure, and the solid residue was added with 100 ml of...

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Abstract

The invention relates to a pH sensitive ketal connection cholesterol-silicon phthalocyanine complex, a preparing method of the pH sensitive ketal connection cholesterol-silicon phthalocyanine complex and application of the pH sensitive ketal connection cholesterol-silicon phthalocyanine complex to medicines. In particular, the invention relates to a silicon phthalocyanine complex shown in the general formula (I), a preparing method of the silicon phthalocyanine complex, a medicine component containing the complex and application of the silicon phthalocyanine complex as a photosensitizer, in particular to application to cancer treatment. All substituting groups in the general formula (I) are the same as definitions in the specification. Due to existence of cholesterol groups, the complex in the series are difficultly taken by cancer cells and normal cells, but in the cancer tissue extracellular micro acid environment, ketal keys are subject to hydrolysis reactions, hydrolysis derivatives of silicon phthalocyanine can be easily taken by the cancer cells, and the extremely-high photosensitive activity is shown; and the complex and the component can be prepared into cancer cell extracellular micro acid environment target photosensitive medicines.

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 the treatment of cancer. [0002] technical background [0003] Photodynamic Therapy (PDT), also known as Photoradiation Therapy (PRT) or Photochemotherapy, is a treatment method based on the principle of photochemical reaction of specific chemical substances. The chemicals used are called tumor chemical diagnosis and treatment drugs (also known as photosensitizers, Photosensitizer, PS for short). The PDT therapy process is to inject a photosensitizer into the body through intravenous injection (for the skin, it can also be applied to the affected area), 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 excited by light , Produce a series ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/02A61K41/00A61K31/695A61P35/00
CPCA61K41/0071C07F7/025
Inventor 蒋雄杰黄华静
Owner SHENZHEN SONO PHOTODYNAMIC BIO MED TECH LTD
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