Phthalocyanine-erlotinib yoke compound and preparation and application thereof

A technology of conjugates and phthalocyanines, which is applied in the field of molecular targeting anticancer photosensitizer erlotinib-phthalocyanine conjugates and its preparation, can solve the problem of unsatisfactory tumor tissue targeting, difficult separation, Synthetic difficulties and other problems, to achieve the effect of low cost, easy to obtain raw materials, and simple synthesis method

Active Publication Date: 2013-09-11
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

[0037] Embodiment 1 (M=Zn, m=2, R 1 , R 2 = -OCH 2 CH 2 OCH 3 , α-position monosubstituted)

[0038] 1) In a 250ml round bottom flask equipped with a temperature-controlled magnetic stirrer, add 24.0g of compound 1, 7.6g of p-toluenesulfonyl chloride and 80ml of CH 2 Cl 2 , after fully stirring and dissolving, add 20g triethylamine, react at room temperature for 10 hours, after the reaction, extract three times with 200ml of 1mol / L hydrochloric acid solution and 200ml saturated saline solution respectively, collect the organic layer and dry it with anhydrous magnesium sulfate, filter Removal of CH by rotary evaporation 2 Cl 2 , to CH 2 Cl 2 with CH 3 A mixed solvent with a volume ratio of OH of 30:1 was used as a developing agent to pass through a silica gel column to obtain compound 2;

[0039] 2) Add 3g of compound 2 and 1gNaN in sequence into a 100ml two-necked bottle equipped with nitrogen gas 3 12ml of acetonitrile was used as the reaction solvent, and refluxe...

Embodiment 2

[0043] Embodiment 2 (M=Zn, m=4, R 1 =R 2 = -OCH 2 CH 2 OCH 3 )

[0044] 1) In a 250ml round bottom flask equipped with a temperature-controlled magnetic stirrer, add 10.0g of compound 1, 8g of p-toluenesulfonyl chloride and 100ml of CH 2 Cl 2 , after fully stirring and dissolving, add 21.2g triethylamine, react at room temperature for 12 hours, after the reaction, extract three times with 200ml of 1mol / L hydrochloric acid solution and 200ml saturated saline solution respectively, collect the organic layer and dry it with anhydrous magnesium sulfate, After filtering, rotary evaporation removes CH 2 Cl 2 , to CH 2 Cl 2 with CH 3 The mixed solvent with OH volume ratio of 30:1 was used as developing agent to pass through the silica gel column to obtain compound 2.

[0045] 2) Add 4.02g of compound 2 and 1gNaN in sequence into a 100ml two-neck bottle equipped with nitrogen gas equipment 3 12ml of acetonitrile was used as the reaction solvent, and refluxed for 24h. After...

Embodiment 3

[0049] Embodiment 3 (M=Al, m=8, R 1 =R 2 = -OCH 2 CH 2 OCH 3 . )

[0050] 1) In a 250ml round bottom flask equipped with a temperature-controlled magnetic stirrer, add 10.0g of compound 1, 9.6g of p-toluenesulfonyl chloride and 100ml of CH 2 Cl 2 , after fully stirring and dissolving, add 25g triethylamine, react at room temperature for 12 hours, after the reaction, extract three times with 200ml of 1mol / L hydrochloric acid solution and 200ml saturated saline solution respectively, collect the organic layer and dry it with anhydrous magnesium sulfate, filter Removal of CH by rotary evaporation 2 Cl 2 , to CH 2 Cl 2 with CH 3 A mixed solvent with a volume ratio of OH of 30:1 was used as a developing agent to pass through a silica gel column to obtain compound 2;

[0051] 2) Add 5.01g of compound 2 and 1gNaN in sequence into a 100ml two-necked bottle equipped with nitrogen ventilation equipment 3 12ml of acetonitrile was used as the reaction solvent, and refluxed fo...

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PUM

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Abstract

The invention discloses a molecular targeting anticancer photosensitizer phthalocyanine-erlotinib yoke compound, and preparation and application thereof. Erlotinib with a long alcoxyl chain is introduced at the periphery of a metal phthalocyanine ring, so that the amphipathy, the bioco mpatibility and the targeting effect of the photosensitizer can be increased. The yoke compound is not easily gathered, which is favorable for improvement of the cell uptake rate; meanwhile, since the compound is single in structure and no isomer exists, the product is easily purified. By adopting the compound, the targeting effect of the photosensitizer in photodynamic therapy is expected to be improved; and meanwhile, the activity of the photosensitizer in the photodynamic therapy is enhanced. The synthesis method of the phthalocyanine-erlotinib yoke compound is simple, involves less side reactions, is high in yield and low in cost; moreover, the raw materials are easily available. Therefore, industrial production is facilitated.

Description

technical field [0001] The invention belongs to the field of synthesis of organic and metal coordination compounds, and relates to a molecularly targeted anticancer photosensitizer erlotinib-phthalocyanine conjugate, a preparation method and application thereof. Background technique [0002] Phthalocyanine is a class of macrocyclic compounds with good photophysical and photochemical properties. It is used in high-tech fields, including semiconductor devices, photovoltaic and solar cells, electrophotography, rectifiers, and photosensitizers for LB film photodynamic therapy. Photosensitizers have great development prospects. [0003] The diversity and structural "tailorability" of phthalocyanine compounds provide the possibility for people to rationally design the required phthalocyanine compounds. Linking phthalocyanine with other functional groups to form new functional materials with complementary functions is one of the important development directions of phthalocyanine c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K41/00A61P35/00
Inventor 薛金萍黄琪李俊张凤玲康心灿
Owner FUZHOU UNIV
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