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

A technology for silicon phthalocyanine and derivatives, applied in the field of silicon phthalocyanine modified by cytidine derivatives and its preparation, can solve the problems of lack of tumor tissue and cancer cell selectivity, limited clinical application, high skin phototoxicity, etc. Fast preparation, easy separation and purification, high biocompatibility and selectivity

Active Publication Date: 2015-03-04
FUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Silicon phthalocyanine modified by cytidine derivative and preparation method and application thereof
  • Silicon phthalocyanine modified by cytidine derivative and preparation method and application thereof
  • Silicon phthalocyanine modified by cytidine derivative and preparation method and application thereof

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preparation example Construction

[0032] The preparation method of cytidine derivative modified silicon phthalocyanine of the present invention is: (1) under ice-water bath ~ room temperature, cytidine (or 5-azacytidine, or 5-fluorocytidine, or 5-methylcytidine) and p-toluenesulfonic acid were placed in acetone and stirred for 2~20 hours, the molar ratio of the two was 1:8~12, and purified by solvent method, extraction method and chromatography to obtain 2', 3'-O-iso Propyl-cytidine (or 2', 3'-O-isopropyl-5-azacytidine, or 2', 3'-O-isopropyl-5-fluorocytidine, or 2', 3' -O-isopropyl-5-methylcytidine).

[0033] (2) with dichlorosilyl phthalocyanine and 2', 3'-O-isopropyl-cytidine (or 2', 3'-O-isopropyl-5-azacytidine, or 2', 3' -O-isopropyl-5-fluorocytidine, or 2', 3'-O-isopropyl-5-methylcytidine) as the reactant, the molar ratio of the two is 1:4~10; Using toluene, xylene or dioxane as a solvent, the amount of solvent used is 40-400ml for 1mmol of dichlorosilicon phthalocyanine, and reacted at 100-130°C for 18...

Embodiment 1

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

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

[0043] Dissolve 250 mg (1 mmol) of cytidine 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. Slowly add the acetone solution of p-toluenesulfonate to the acetone solution of cytidine in an ice-water bath, stir at room temperature for 4-10 hours (preferably 6 hours), centrifuge to collect the white precipitate, wash the precipitate with acetone three to four times, and dissolve it with a small amount of DMF , add ethyl acetate to precipitate, membrane filtration, vacuum drying to obtain a white powder product with a yield of 95%.

[0044] The characterization data of the product are as follows: IR (KBr, cm -1 ): 1383 (CH 3 ); 1123 (-O-); 1727 (C=O); 3067, 1204, 1650 (NH 2 ); 1693 (C=C); 3067, 1204 (-OH).

[0045] 1 H NMR (DMSO-d6, 400MHz, pp...

Embodiment 2

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

[0054] (1) Synthesis of 2’, 3’-O-isopropyl-5-azacytidine

[0055] Dissolve 244 mg (1 mmol) of 5-azacytidine 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. Slowly add the p-toluenesulfonic acid acetone solution dropwise into the 5-azacytidine acetone solution under an ice-water bath, and stir at room temperature for 12-36 h (preferably 24 h). Sodium bicarbonate solution was slowly added to the reaction mixture with stirring until the bubbles disappeared and a white precipitate formed. Filter, wash twice with acetone, and dry to obtain a white powder product with a yield of 90%.

[0056] The characterization data of the product are as follows: IR (KBr, cm -1 ): 1110 (C-O-C); 1693 (-CO-N); 3414.7, 1212, 1610 (NH 2 ); 1693 (C=C); 3291, 1158 (-OH); 1470 (-CH 2 -).

[0057] 1 H NMR (...

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Abstract

The invention discloses silicon phthalocyanine modified by a cytidine 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 cytidine 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 silicon phthalocyanine modified by cytidine derivatives and its preparation method and application. 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 (Photodyn...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H23/00C07H1/00A61K41/00A61K49/00A61K31/7068A61P35/00A61P35/02A61P31/04A61P31/10A61P1/02A61P27/02A61P9/10A61P17/02A61P17/00A61P31/12
Inventor 黄剑东沈小敏
Owner FUZHOU UNIV
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