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Amino phenoxy substituted phthalocyanine and application thereof to pharmaceutical field

A technology of aminophenoxytetra, phenoxy, which is applied in the field of photothermal agents and photothermal therapy drugs, can solve the problems that have not yet been seen in the application research and limitations of photothermal therapy, and achieve good industrialization prospects, simple operation, Effects that are easy to store

Active Publication Date: 2018-02-23
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in terms of cancer treatment, the research on phthalocyanine is currently limited to photodynamic therapy (PDT), and there is no application research on it as photothermal therapy.

Method used

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  • Amino phenoxy substituted phthalocyanine and application thereof to pharmaceutical field
  • Amino phenoxy substituted phthalocyanine and application thereof to pharmaceutical field
  • Amino phenoxy substituted phthalocyanine and application thereof to pharmaceutical field

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Synthesis of aminophenoxy tetrasubstituted hollow phthalocyanine with the structure shown in the following formula

[0066] in:

[0067] The compound can be named: Tetra-α-(3-(N,N-dimethylamino)-phenoxy) hollow phthalocyanine, and the preparation method is as follows:

[0068](1) Preparation of (3-(N,N-dimethylamino)-phenoxy)phthalonitrile: Reaction of 3-nitrophthalonitrile and N,N-dimethylm-hydroxyaniline The material, the feed ratio of the two is 1:1~1.5, with dimethyl sulfoxide as solvent, the solvent consumption is that every mmol 3-nitrophthalonitrile needs 3~4mL, in the presence of potassium carbonate and under the protection of nitrogen, Stir the reaction at room temperature to 60°C for 48 to 72 hours. Wherein the dosage of potassium carbonate is 1.5-3 mmol per mmol of 3-nitrophthalonitrile. Monitored by thin-layer chromatography, when 3-nitrophthalonitrile is basically consumed, the reaction is terminated, add water and stand for 4-8 hours, precipitate, d...

Embodiment 2

[0078] Synthesis of aminophenoxy hollow phthalocyanine tetraiodide salt with the structure shown in the following formula

[0079] in:

[0080] The compound can be named: tetra-α-(3-(N,N-dimethylamino)-phenoxy) hollow phthalocyanine tetraiodide salt, and the preparation method is as follows:

[0081] React 0.036 mmol of tetrakis-α-(3-(N,N-dimethylamino)-phenoxy) hollow phthalocyanine described in Example 1 with methyl iodide in an amount of 2.9 to 3.6 mL (preferably 3 mL ), the solvent used is DMF and CHCl 3 The mixed solution (1 / 1) is used in an amount of 2.9-7.2mL (preferably 4mL), and reacted at 25-50°C for 24-48h (preferably 36h). A small amount of DMF was left by rotary evaporation, which was added dropwise to DCM, and a blue precipitate was precipitated, filtered through micropores, washed several times with dichloromethane, and dried in vacuo to obtain a solid with a yield of 89%.

[0082] The characterization data of the product are as follows:

[0083] HRMS(ES...

Embodiment 3

[0086] Synthesis of aminophenoxyphthalocyanine zinc with the structure shown in the following formula

[0087] where M=Zn,

[0088] The compound can be named: tetra-α-(3-(N,N-dimethylamino)-phenoxy)zinc phthalocyanine, and the preparation method is as follows:

[0089] With (3-(N,N-dimethylamino)-phenoxy)phthalonitrile 4mmol as reactant, n-pentanol 32-40mL (preferably 35mL) as solvent, add anhydrous zinc acetate (or other Zinc salt) 1-3mmol (preferably 2mmol), and DBU 0.8-2.4mL (preferably 1.2mL), stirred and reacted at 130-150°C for 12-18 hours, and monitored the reaction end point by thin-layer chromatography. Rotary evaporation, dissolved in dichloromethane, petroleum ether: DCM = 2: 1, passed through a silica gel column, washed away the first reddish-yellow band, then collected the yellow-green band with ethyl acetate, spin-dried, and passed through a tetrahydrofuran gel column, After the collected dark green band was spin-dried, DMF was added to dissolve it, and wat...

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Abstract

The invention discloses amino phenoxy substituted phthalocyanine as well as a preparation method and application thereof. The amino phenoxy substituted phthalocyanine disclosed by the invention has the following characteristics that an amino has a PET (Polyethylene Terephthalate) effect and has relatively weak fluorescence emission in water, so that photothermal conversion of phthalocyanine is facilitated; particularly, (3-(N,N-dimethylamino)-phenoxy)tetra-substituted zinc phthalocyanine and (3-(N,N-dimethylamino)-phenoxy)tetra-substituted hollow phthalocyanine have a good photothermal effectand an in-vitro anti-tumor effect, so that the amino phenoxy substituted phthalocyanine is a novel organic photothermal material.

Description

technical field [0001] The invention belongs to the field of photothermal agents and photothermal therapeutic drugs, and specifically relates to an aminophenoxy substituted phthalocyanine and its preparation method and application. Background technique [0002] With the development of science and technology, new tumor treatment methods continue to emerge. Among them, photodynamic therapy (PDT) and photothermal therapy (PTT) have attracted extensive attention and research due to their high selectivity to tumor tissue, small trauma, and low toxicity and side effects. [0003] PDT kills cancer cells by using photosensitizers to generate reactive oxygen species (Reactive oxygen species, ROS) under light. According to the type of ROS and the way of production, PDT can be divided into two mechanisms: type I and type II. In the type I mechanism, the excited-state photosensitizer directly undergoes electron transfer with biomolecules to generate free radical species, and these fre...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K41/00A61P35/00
CPCA61K41/0071C07D487/22
Inventor 黄剑东李兴淑彭小慧
Owner FUZHOU UNIV
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