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A kind of axial nucleoside asymmetrically modified silicon phthalocyanine and its preparation method and application

An asymmetric, silicon phthalocyanine technology, applied in the field of axial nucleoside asymmetric modification of silicon phthalocyanine and its preparation, can solve the problems of lack of tumor tissue and cancer cell selectivity, high skin phototoxicity, and clinical application limitations. , to achieve the effect of excellent amphiphilicity, clear structure and unique asymmetric substitution characteristics

Active Publication Date: 2016-01-27
FUZHOU UNIV
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  • Summary
  • 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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  • A kind of axial nucleoside asymmetrically modified silicon phthalocyanine and its preparation method and application
  • A kind of axial nucleoside asymmetrically modified silicon phthalocyanine and its preparation method and application
  • A kind of axial nucleoside asymmetrically modified silicon phthalocyanine and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Synthesis of bis[5'-(2',3'-O-isopropyl)-uridineoxy]silicon phthalocyanine

[0043] (1) Synthesis of 2',3'-O-isopropyl-uridine

[0044] 245 mg (1 mmol) of uridine is dissolved in 10-30 ml (preferably 20 ml) of acetone, and 8-12 mmol (preferably 10 mmol) of p-toluenesulfonic acid is dissolved in 10-30 ml (preferably 20 ml) of acetone. The acetone p-toluenesulfonic acid solution was slowly added dropwise to the uridine acetone solution in an ice-water bath, and stirred at room temperature for 2 to 10 hours (preferably 6 hours). The reaction mixture was added to an ice-water solution containing 4% sodium bicarbonate, extracted several times with dichloromethane (or chloroform), the organic layer was collected, dried over magnesium sulfate, filtered, concentrated, and dried to obtain a yellow powder product. Yield 85%.

[0045] The characterization data of the product are as follows: MS (EI-60) m / z: 283.4 [M-H] - .

[0046] IR (KBr, cm -1 ): 1467, 2935 (CH 3 ); 1703 (C...

Embodiment 2

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

[0057] (1) Synthesis of 2',3'-O-isopropyl-cytidine

[0058] 250 mg (1 mmol) of cytidine is dissolved in 10-30 ml (preferably 20 ml) of acetone, and 8-12 mmol (preferably 10 mmol) of p-toluenesulfonic acid is dissolved in 10-30 ml (preferably 20 ml) of acetone. The acetone p-toluenesulfonic acid solution was slowly added dropwise to the cytidine acetone solution in an ice-water bath, stirred at room temperature for 4~10h (preferably 6h), centrifuged to collect the white precipitate, washed with acetone three to four times, and dissolved with a small amount of DMF. Ethyl acetate was added for precipitation, membrane filtration, and vacuum drying to obtain a white powdery product with a yield of 95%.

[0059] 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).

[0060] 1 HNMR (...

Embodiment 3

[0068] Synthesis of bis[5'-(2',3'-O-isopropyl)-adenosyloxy]silicon phthalocyanine

[0069] (1) Synthesis of 2',3'-O-isopropyl-adenosine

[0070] Adenosine (1 mmol) is dissolved in 10-30 ml (preferably 20 ml) of acetone, and 8-12 mmol (preferably 10 mmol) of p-toluenesulfonic acid is dissolved in 10-30 ml (preferably 20 ml) of acetone. The acetone p-toluenesulfonic acid solution was slowly added dropwise to the 2-aminoadenosylacetone solution in an ice-water bath, stirred at room temperature for 24~72h (preferably 6h), poured into a 4% aqueous sodium bicarbonate solution, a white precipitate was precipitated, and the Filter and dry. Purified by Soxhlet extraction with chloroform, and dried to obtain a white powder product. Yield 85%.

[0071] (2) Synthesis of bis[5'-(2',3'-O-isopropyl)-adenosyloxy]silicon phthalocyanine

[0072] Under nitrogen protection, dichlorosilicon phthalocyanine (40mg, 0.065mmol), 2',3'-O-isopropyl-adenosine (0.260~0.650mmol, preferably 0.52mmol) and...

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Abstract

The invention discloses a silicon phthalocyanine asymmetrically modified by axial nucleosides, a preparation method and application thereof, and belongs to the field of preparation of photodynamic drugs or photosensitizers. The axial nucleoside asymmetrically modified silicon phthalocyanine provided by the present invention can be used as a photosensitizer for photodynamic therapy, photodynamic diagnosis or photodynamic disinfection. It has the structural characteristics of axial asymmetric substitution and shows good amphiphile and high photodynamic activity.

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 asymmetrically modified by axial nucleosides and a preparation method and application thereof. Background technique [0002] Phthalocyanine compounds 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 is possible to develop oxidation catalysts, desulfurization catalysts, nonlinear optical materials, photosensitive drugs, liquid crystal materials, optical recording materials or photoconductive materials, but how to regulate substituents and central ions To obtain the target functional compound, it requires creative work. [0003] The application prospect of phthalocyanine compounds as photosensitizers in photodyna...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/10A61K41/00A61K31/695A61P35/00A61P35/02A61P31/04A61P1/02A61P27/02A61P9/10A61P17/02A61P17/00A61P31/12A61P31/10
Inventor 黄剑东石杰
Owner FUZHOU UNIV
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