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Targeted anti-cancer molecule gefitinib phthalocyanine conjugate, and preparation and application thereof

A conjugate and targeting technology, which is applied in the direction of active ingredients of silicon compounds, medical preparations containing active ingredients, compounds of group 4/14 elements of the periodic table, etc., can solve the problems of difficult separation, difficult synthesis, and side reactions Waiting for questions

Active Publication Date: 2014-03-12
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the existing substituted phthalocyanine metal complexes have problems such as difficult synthesis, many side reactions, and difficult separation.
At the same time, there is an important problem that the targeting of phthalocyanine to tumor tissue is not ideal, so the research on the targeting of photosensitizers has become a hot research topic now.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 (M=Zn, n=2, α unit substitution)

[0043] 1) Add 12.0g of compound to a 350ml round bottom flask equipped with a temperature-controlled magnetic stirrer 1 , 3.8g p-toluenesulfonyl chloride and 40ml CH 2 Cl 2 After fully stirring and dissolving, add 10g triethylamine, react at room temperature for 10 hours, after the reaction, extract three times with 200ml saturated sodium chloride solution and 200ml 1mol / L hydrochloric acid solution respectively, collect the organic layer and dry it with anhydrous magnesium sulfate , filtered and rotary evaporated to remove CH 2 Cl 2 , in CH with a volume ratio of 30:1 2 Cl 2 with CH 3 The mixed solvent of OH is the developing solvent and passed through a silica gel column to obtain compound 1a;

[0044] 2) In a 150ml double-neck flask equipped with a nitrogen-passing device, add 3g of compounds in turn 1a , 0.8gNaN 3 , 15ml of acetonitrile was used as the reaction solvent, refluxed for 24h, after the reaction was ov...

Embodiment 2

[0057] Example 2 (M=Zn, n=2, β unit substitution)

[0058] 1) Add 12.0g of compound to a 350ml round bottom flask equipped with a temperature-controlled magnetic stirrer 1 , 3.8g p-toluenesulfonyl chloride and 40ml CH 2 Cl 2 , after fully stirring and dissolving, add 10g triethylamine, react at room temperature for 10 hours, after the reaction, extract three times with 200ml 1mol / L hydrochloric acid solution and 200ml saturated sodium chloride solution respectively, collect the organic layer and dry it with anhydrous magnesium sulfate , filtered and rotary evaporated to remove CH 2 Cl 2 , with CH 2 Cl 2 with CH 3 A mixed solvent with a volume ratio of OH of 30:1 was used as a developing solvent to pass through a silica gel column to obtain compound 1a;

[0059] 2) In a 150ml double-neck flask equipped with a nitrogen-passing device, add 3g of compounds in turn 1a , 0.8gNaN 3 , 15ml of acetonitrile was used as the reaction solvent, refluxed for 24h, after the reaction ...

Embodiment 3

[0066] Example 3 (M=Al, n=2, α monosubstituted)

[0067] 1) Add 12.0g of compound to a 350ml round bottom flask equipped with a temperature-controlled magnetic stirrer 1 , 3.8g p-toluenesulfonyl chloride and 40ml CH 2 Cl 2 , after fully stirring and dissolving, add 10g triethylamine, react at room temperature for 10 hours, after the reaction, extract three times with 200ml 1mol / L hydrochloric acid solution and 200ml saturated sodium chloride solution respectively, collect the organic layer and dry it with anhydrous magnesium sulfate , filtered and rotary evaporated to remove CH 2 Cl 2 , with CH 2 Cl 2 with CH 3 A mixed solvent with a volume ratio of OH of 30:1 was used as a developing solvent to pass through a silica gel column to obtain compound 1a;

[0068] 2) In a 150ml double-neck flask equipped with a nitrogen-passing device, add 3g of compounds in turn 1a , 0.8gNaN 3 , 15ml of acetonitrile was used as the reaction solvent, refluxed for 24h, after the reaction wa...

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PUM

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Abstract

The invention discloses a targeted anti-cancer molecule gefitinib phthalocyanine conjugate, and a preparation method and application thereof. The molecular formula of the gefitinib phthalocyanine conjugate is C56+2nH42+4nO5+nClFN12Zn (n=2-8). Gefitinib with an alkoxyl long chain is introduced into the periphery of a metal phthalocyanine large ring, so the amphipathicity and the biocompatibility can be improved, and the targeting property of a photosensitizer is enhanced. The gefitinib phthalocyanine conjugate is difficult to aggregate, so the cellular uptake ratio is increased and the activity of the photosensitizer in photodynamic therapy is also enhanced. The compound has single structure, is not provided with an isomer, and is easy to purify. A synthesis method is simple, little in side reaction, high in yield, easily available in raw materials, low in cost and favorable for industrialized production.

Description

technical field [0001] The invention belongs to the field of synthesis of organic and metal coordination compounds, and relates to a targeted anticancer molecule gefitinib phthalocyanine conjugate and its preparation method and application. Background technique [0002] Phthalocyanine compound is a sixteen-membered ring large π system, which has good light, heat and chemical stability, excellent optical, magnetic and electrical properties, so phthalocyanine complexes are widely used in many fields, such as biosensors, non-toxic Linear optical materials, dye-sensitized photovoltaic products, semiconductor materials, oxidation or reduction catalysts, etc. In addition, phthalocyanines are the most promising class of photosensitizers in photodynamic therapy due to their strong absorption in the near-infrared region and the ability to generate cytotoxic reactive oxygen species. [0003] The diversity and structural "modification" of phthalocyanine compounds provide the possibili...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K41/00A61K31/5377A61P35/00
CPCA61K31/5377A61K31/695A61K41/0071C07D487/22C07F7/10
Inventor 薛金萍周晓琴黄琪张明俊
Owner FUZHOU UNIV
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