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Silicon phthalocyanine modified by adenosine derivative and preparation method and application thereof

An adenosine derivative and silicon phthalocyanine technology, which is applied in the field of adenosine derivative-modified silicon phthalocyanine and its preparation, can solve the problems of lack of tumor tissue and cancer cell selectivity, high skin phototoxicity, and limited clinical application. , to achieve the effect of fast preparation, high biocompatibility and selectivity, and easy separation and purification

Active Publication Date: 2012-12-19
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Hematoporphyrin derivatives have shown certain curative effects, but also exposed serious disadvantages: the maximum absorption wavelength (380-420nm) is not in the red light region (650-800nm) with better transmittance to human tissue, and the skin has high phototoxicity. It is a mixture and its composition is unstable, so its clinical application is limited, so the development of a new generation of photodynamic drugs (photosensitizers) is an international research hotspot
In addition, the current photosensitizers (including phthalocyanine photosensitizers) in clinical trials still lack selectivity to tumor tissues and cancer cells, which is also a problem that needs to be overcome at present

Method used

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Examples

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Effect test

preparation example Construction

[0031] Preparation method of silicon phthalocyanine modified by adenosine derivative of the present invention

[0032] (1) In an ice-water bath to room temperature, mix adenosine (or 2-aminoadenosine, or 6-chloropurine nucleoside, or 2-chloroadenosine, or 2, 6-dichloropurine nucleoside) and p-toluenesulfonate The acid is placed in acetone and stirred for 2-20 hours, the molar ratio of the two is 1:8-12, and purified by solvent method, extraction method and chromatography to obtain 2', 3'-O-isopropyl-adeno Glycoside (or 2', 3'-O-isopropyl-2-aminoadenosine, or 2', 3'-O-isopropyl-6-chloropurine nucleoside, or 2-chloroadenosine, or 2 ', 3'-O-isopropyl-2, 6-dichloropurine nucleoside).

[0033] (2) with dichlorosilyl phthalocyanine and 2', 3'-O-isopropyl-adenosine (or 2', 3'-O-isopropyl-2-aminoadenosine, or 2', 3' -O-isopropyl-6-chloropurine nucleoside, or 2', 3'-O-isopropyl-2-chloroadenosine, or 2', 3'-O-isopropyl-2, 6- Dichloropurine nucleoside) as the reactant, the molar ratio...

Embodiment 1

[0041] Synthesis of Bis[5'-(2', 3'-O-isopropyl)-adenosyloxy]silyl phthalocyanine

[0042] (1) Synthesis of 2’, 3’-O-isopropyl-adenosine

[0043] Dissolve adenosine (1 mmol) in 10-30 ml (preferably 20 ml) of acetone, and 8-12 mmol (preferably 10 mmol) of p-toluenesulfonic acid in 10-30 ml (preferably 20 ml) of acetone. Add p-toluenesulfonic acid acetone solution slowly dropwise to 2-aminoadenosine acetone solution under ice-water bath, stir at room temperature for 24~72 h (preferably 6 h), pour into 4% sodium bicarbonate ice water solution, and precipitate white precipitate, Suction filter and dry. Purified by Soxhlet extraction with chloroform, and dried to obtain a white powder product. Yield 85%.

[0044] (2) Synthesis of bis[5'-(2',3'-O-isopropyl)-adenosyloxy]silicone phthalocyanine

[0045] Under nitrogen protection, dichlorosilicon phthalocyanine (40 mg, 0.065mmol), 2',3'-O-isopropyl-adenosine (0.260~0.650mmol, preferably 0.52mmol) and NaH (0.48~0.60mmol , preferably...

Embodiment 2

[0053] Synthesis of Bis[5'-(2', 3'-O-isopropyl)-2-aminoadenosyloxy]silicone phthalocyanine

[0054] (1) Synthesis of 2’, 3’-O-isopropyl-2-aminoadenosine

[0055]Dissolve 2-aminoadenosine (1 mmol) in 10-30 ml (preferably 20 ml) of acetone, and dissolve 8-12 mmol (preferably 10 mmol) of p-toluenesulfonic acid in 10-30 ml (preferably 20 ml) of acetone. Add p-toluenesulfonic acid acetone solution slowly dropwise to 2-aminoadenosine acetone solution under ice-water bath, stir at room temperature for 24~72 h (preferably 6 h), pour into 4% sodium bicarbonate ice water solution, and precipitate white precipitate, Suction filter and dry. Purified by Soxhlet extraction with chloroform, and dried to obtain a white powder product. The yield is 80%.

[0056] (2) Synthesis of bis[5'-(2', 3'-O-isopropyl)-2-aminoadenosyloxy]silicone phthalocyanine

[0057] Under nitrogen protection, dichlorosilicon phthalocyanine (40 mg, 0.065 mmol), the above-mentioned isopropylidene protection product o...

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Abstract

The invention discloses silicon phthalocyanine modified by an adenosine derivative and a preparation method and an application thereof, which belong to the field of preparation of photodynamic medicaments or photosensitizers. The silicon phthalocyanine modified by the adenosine derivative provided by the invention can be taken as a photosensitizer for use in photodynamic therapy, photodynamic diagnosis or photodynamic disinfection, has the advantages of high selectivity, high photodynamic activity and the like, has definite constitution, is easy and convenient to prepare, and is easy to be industrialized.

Description

technical field [0001] The invention belongs to the field of preparation of photodynamic drugs or photosensitizers, and in particular relates to a silicon phthalocyanine modified by adenosine derivatives and a preparation method and application thereof. Background technique [0002] Phthalocyanine complexes are an important class of functional materials, which can be developed into functional materials for different purposes through different structural modifications. By introducing suitable substituents and central ions on the phthalocyanine ring, it can be developed into oxidation catalysts, desulfurization catalysts, nonlinear optical materials, photosensitizers, liquid crystal materials, optical recording materials or photoconductive materials, but how to regulate substituents and central ions It is a very complicated task to obtain the target functional compound. [0003] The application prospect of phthalocyanine complexes as photosensitizers in photodynamic therapy ...

Claims

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Application Information

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IPC IPC(8): C07H23/00C07H1/00A61K31/7076A61K41/00A61P31/00A61P35/00A61P35/02A61P31/04A61P1/02A61P27/02A61P9/10A61P17/00A61P31/12A01N43/90A01P1/00A01P3/00
Inventor 黄剑东沈小敏郑碧远李中井
Owner FUZHOU UNIV
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