A Molecularly Targeted Anticancer Photosensitizer Erlotinib-Phthalocyanine Conjugate

A technology of molecular targeting and photosensitizers, which can be applied in drug combinations, antineoplastic drugs, medical preparations containing active ingredients, etc., can solve the problems of poor tumor tissue targeting, difficult separation, and many side effects , to achieve the effect of low cost, easy access to raw materials, and less side reactions

Active Publication Date: 2016-10-26
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

[0048] Embodiment 1 (M=Zn, m=3, R=-CH 3 O, α-position monosubstituted)

[0049] 1) Add 1.0g (5.07mmol) of the compound and 1.0g (10mmol) of formamidine acetate into 20ml of ethanol solution, and microwave for 3h. After the reaction was completed, the ethanol was spin-dried, and then extracted with dichloromethane and water to obtain a crude product. Afterwards, compound 2 was isolated by passing through a silica gel column with dichloromethane-methanol as the eluent.

[0050] ), adding 1g (4.8mmol) of compound 2 to 1.48g (9.7mmol) of phosphorus oxychloride, reacting for 4-9h, rotary evaporating to remove the remaining phosphorus oxychloride, and then extracting with water and dichloromethane to obtain the crude product. Compound 3 was obtained by passing through a silica gel column.

[0051] 3) Add 1g (4.46mmol) of compound 3 and 1g (8.92mmol) of 3-aminophenylacetylene into isopropanol. After reacting for 4-9 hours, the isopropanol was spin-dried, and then dichloromethane-...

Embodiment 2

[0056] Example 2 (M=Al, m=7, R=-H, α-position monosubstituted)

[0057] 1) Add 1g (mmol) of the compound and 1.0g (mmol) of formamidine acetate into 20ml of ethanol solution, and microwave for 3h. After the reaction was completed, the ethanol was spin-dried, and then extracted with dichloromethane and water to obtain a crude product. Afterwards, compound 2 was isolated by passing through a silica gel column with dichloromethane-methanol as the eluent.

[0058] 2) Add 1g (mmol) of compound 2 to 1.48g (mmol) of phosphorus oxychloride, react for 4-9 hours, remove the remaining phosphorus oxychloride by rotary evaporation, and then extract with water and dichloromethane to obtain the crude product. Compound 3 was obtained after passing through a silica gel column.

[0059] 3) Add 1g (mmol) of compound 3 and 1g (mmol) of 3-aminophenylacetylene into isopropanol. After reacting for 4-9 hours, the isopropanol was spin-dried, and the compound 4 was obtained by separation on a silica...

Embodiment 3

[0064] Embodiment 3 (M=Si, m=1, R=-CH 2 OCH 2 CH 2 OCH 3 , α-position monosubstituted)

[0065] 1) Add 1.0 g of compound 1 and 1.0 g of formamidine acetate into 20 ml of ethanol solution, and react with microwave for 3 h. After the reaction was completed, the ethanol was spin-dried, and then extracted with dichloromethane and water to obtain a crude product. Afterwards, compound 2 was isolated by passing through a silica gel column with dichloromethane-methanol as the eluent.

[0066] ), adding 1g of compound 2 to 1.51g of phosphorus oxychloride, reacting for 4-9h, rotary evaporation to remove the remaining phosphorus oxychloride, and then extracting with water and dichloromethane to obtain the crude product. Compound 3 was obtained after passing through a silica gel column.

[0067] 3) Add 1g of compound 3 and 1g of 3-aminophenylacetylene into isopropanol. After reacting for 4-9 hours, the isopropanol was spin-dried, and the compound 4 was obtained by separation on a s...

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PUM

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Abstract

The invention discloses a molecularly targeted anticancer photosensitizer erlotinib-phthalocyanine conjugate and application thereof. An erlotinib structural unit with a long alkoxy chain is introduced into the periphery of a metal phthalocyanine big ring, so that the amphipathicity, biocompatibility and targeting property of the photosensitizer can be improved. The conjugate is difficult to aggregate, and the cellular uptake ratio is improved; and meanwhile, the compounds are simple in structure, an isomer does not exist, and the product is easy to purify. According to the compound, the targeting property of the photosensitizer in photodynamics therapy is expected to be improved, and the activity of the photosensitizer in photodynamics therapy is enhanced. The synthetic method is simple, fewer side reactions are carried out, the yield is high, the raw materials are readily available, the cost is low, and the industrial production is realized.

Description

[0001] This case is a divisional application of [0002] The application number of the original application: 201310240667.4 [0003] Filing date of the original application: 2013-6-18 [0004] Invention title of the original application: a molecularly targeted anticancer photosensitizer erlotinib-phthalocyanine conjugate. technical field [0005] The invention belongs to the field of synthesis of organic and metal coordination compounds, and relates to a molecular targeting anticancer photosensitizer erlotinib-phthalocyanine conjugate and its application. Background technique [0006] 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. [0007] The diversity and structural "tailorability" of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22A61K41/00A61P35/00
CPCA61K41/0076C07D487/22
Inventor 薛金萍张凤玲黄琪李俊
Owner FUZHOU UNIV
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