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Erlotinib-phthalocyanine conjugate as molecule-targeting anticancer photosensitizer

A molecular targeting and photosensitizer technology, applied in the field of molecular targeting anticancer photosensitizer erlotinib-phthalocyanine conjugate and preparation thereof, can solve the problem that tumor tissue targeting is not ideal, separation is difficult, and Synthesis difficulties and other problems, to achieve the effects of low cost, easy availability of raw materials, and simple synthesis methods

Active Publication Date: 2013-10-09
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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  • Erlotinib-phthalocyanine conjugate as molecule-targeting anticancer photosensitizer
  • Erlotinib-phthalocyanine conjugate as molecule-targeting anticancer photosensitizer
  • Erlotinib-phthalocyanine conjugate as molecule-targeting anticancer photosensitizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1 (M=Zn, m=3, R=-CH 3 O, α-position monosubstituted)

[0045] 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. After using dichloromethane-methanol as the eluent through a silica gel column, the compound is isolated 2。

[0046] ） , 1 g (4.8 mmol) of the compound 2 Add 1.48g (9.7mmol) phosphorus oxychloride, react for 4-9h, remove the remaining phosphorus oxychloride by rotary evaporation, and then extract with water and dichloromethane to obtain crude product. The compound was obtained by passing through a silica gel column 3 .

[0047] 3), 1g (4.46mmol) compound 3 and 1 g (8.92 mmol) of 3-aminophenylacetylene were added to isopropanol. After reacting for 4-9h, spin the isopropanol to dryness, then use dichloromethane-methanol as t...

Embodiment 2

[0052] Example 2 (M=Al, m=7, R=-H, α-position monosubstituted)

[0053] 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. After using dichloromethane-methanol as the eluent through a silica gel column, the compound is isolated 2。

[0054] 2), 1g (mmol) compound 2 Add 1.48g (mmol) phosphorus oxychloride, react for 4-9h, remove the remaining phosphorus oxychloride by rotary evaporation, and then extract with water and dichloromethane to obtain crude product. After passing through a silica gel column to obtain the compound 3 .

[0055] 3), 1g (mmol) compound 3 and 1 g (mmol) of 3-aminophenylacetylene were added to isopropanol. After reacting for 4-9 hours, the isopropanol was spin-dried, and then dichloromethane-methanol was used as the eluent, and the compound w...

Embodiment 3

[0060] Embodiment 3 (M=Si, m=1, R=-CH 2 OCH 2 CH 2 OCH 3 , α-position monosubstituted)

[0061] 1), 1.0g compound 1 And 1.0g of formamidine acetate was added to 20ml of ethanol solution, microwave reaction for 3h. After the reaction was completed, the ethanol was spin-dried, and then extracted with dichloromethane and water to obtain a crude product. After using dichloromethane-methanol as the eluent through a silica gel column, the compound is isolated 2。

[0062] ） , the 1g compound 2 Add 1.51g of phosphorus oxychloride, react for 4-9h, remove the remaining phosphorus oxychloride by rotary evaporation, and then extract with water and dichloromethane to obtain the crude product. After passing through a silica gel column to obtain the compound 3 .

[0063] 3), 1g compound 3 and 1 g of 3-aminophenylacetylene were added to isopropanol. After reacting for 4-9 hours, the isopropanol was spin-dried, and then dichloromethane-methanol was used as the eluent, and the comp...

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PUM

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Abstract

The invention discloses an erlotinib-phthalocyanine conjugate as a molecule-targeting anticancer photosensitizer and its preparation method and use. Erlotinib structure units with alcoxyl long-chains are introduced to the periphery of a metal phthalocyanine large-ring so that amphipathy, biocompatibility and photosensitizer targeting are improved. The erlotinib-phthalocyanine conjugate is not aggregated easily, is conducive to cell uptake ratio improvement, has a single structure, has no isomers and can be purified easily. The erlotinib-phthalocyanine conjugate can improve photosensitizer targeting in photodynamic therapy and improve photosensitizer activity in photodynamic therapy. The preparation method has simple processes, less side reactions and a high yield, adopts easily available raw materials, has a low cost and is conducive to industrial production.

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): A61K41/00A61P35/00
Inventor 薛金萍张凤玲黄琪李俊
Owner FUZHOU UNIV
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