Phthalocyanine metal complex containing piperazine ethyoxyl modification group and preparing method thereof

A technology of metal complexes and substituent groups, applied in the field of phthalocyanine metal complexes and its preparation, can solve the problems of high skin phototoxicity, poor bioselectivity, lack of amphiphilicity, etc.

Active Publication Date: 2012-09-19
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Hematoporphyrin derivatives have shown certain curative effects, but also exposed serious disadvantages: the maximum absorption wavelength (380-420nm) is not in the red light region (650-800nm) with better transmittance to human tissue, and the skin has high phototoxicity. It is a mixture and its composition is unstable, so its clinical application is limited, so the development of a new generation of photodynamic drugs (photosensitizers) is an international research hotspot
However, currently reported biologically active phthalocyanine complexes still have deficiencies, such as lack of amphiphilicity, poor stability, complex synthetic routes, or poor bioselectivity, etc., which need further improvement.

Method used

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  • Phthalocyanine metal complex containing piperazine ethyoxyl modification group and preparing method thereof
  • Phthalocyanine metal complex containing piperazine ethyoxyl modification group and preparing method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Synthesis and Physicochemical Properties of 1,8(11), 15(18), 22(25)-tetrakis[2-(N-tert-butoxycarbonylpiperazinyl)ethoxy]zinc phthalocyanine

[0051]

[0052] Formula 1)

[0053] This compound can also be called four-a-[2-(N-tert-butoxycarbonylpiperazinyl)ethoxy]zinc phthalocyanine, and its structure is shown in formula (1), wherein:

[0054] .

[0055] (1) Protect the terminal amino group of N-hydroxyethylpiperazine by BOC (tert-butoxycarbonyl): in 20~60ml (preferably 30 ml) CH 2 Cl 2 Add 20mmol N-hydroxyethylpiperazine and 20~40mmol (preferably 30 mmol) triethylamine, then slowly add 20~50mmol (preferably 40 mmol) di-tert-butyl dicarbonate dropwise, and stir at 0°C for 0.5~2 hours (Preferably 1 hour), then stir the reaction at 30°C, monitor by thin-layer chromatography, and stop the reaction when the N-hydroxyethylpiperazine is substantially consumed. Removal of CH by rotary evaporation 2Cl 2 and triethylamine, the obtained pale yellow oily liquid was washed...

Embodiment 2

[0061] Synthesis and Physicochemical Properties of 1,8(11), 15(18), 22(25)-Tetrakis(2-piperazinylethoxy)zinc Phthalocyanine

[0062] This compound can also be called four-a-(2-piperazinylethoxy)zinc phthalocyanine, and its structure is shown in formula (1), wherein:

[0063] .

[0064] Under nitrogen protection conditions, 0.25mmol tetra-a-[2-(N-tert-butoxycarbonylpiperazinyl)ethoxy]zinc phthalocyanine obtained in Example 1 was added to 5 ml tetrabutylammonium fluoride (TBAF) in tetrahydrofuran solution, the concentration of tetrabutylammonium fluoride is 0.5~2M (preferably 1M), stirred and refluxed for 5~10 hours, and the reaction end point is monitored by thin layer chromatography. The solvent was removed by rotary evaporation, washed with water, and freeze-dried under reduced pressure. Then use THF as the mobile phase to purify through a gel column, collect dark green components, and dry to obtain 122 mg of product with a yield of 45%. The maximum absorption peak of th...

Embodiment 3

[0067] Synthesis and Physicochemical Properties of 1-[2-(N-tert-butoxycarbonylpiperazinyl)ethoxy]zinc Phthalocyanine

[0068]

[0069] Formula (2)

[0070] The structure of the compound is shown in formula (2), wherein:

[0071] .

[0072] (1) Protect the terminal amino group of N-hydroxyethylpiperazine by BOC (tert-butoxycarbonyl): in 20~60ml (preferably 30 ml) CH 2 Cl 2 Add 20mmol N-hydroxyethylpiperazine and 20~40mmol (preferably 30 mmol) triethylamine, then slowly add 20~50mmol (preferably 40 mmol) di-tert-butyl dicarbonate dropwise, and stir at 0°C for 0.5~2 hours (Preferably 1 hour), then stir the reaction at 30°C, monitor by thin-layer chromatography, and stop the reaction when the N-hydroxyethylpiperazine is substantially consumed. Removal of CH by rotary evaporation 2 Cl 2 and triethylamine, the obtained pale yellow oily liquid was washed with CH 2 Cl 2 Dissolve, wash three times with water, collect the organic phase, anhydrous MgSO 4 After drying, the s...

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Abstract

The invention discloses a phthalocyanine metal complex containing piperazine ethyoxyl modification group and a preparing method thereof and belongs to the field of photodynamic drug preparing or photosensitizer preparing. The phthalocyanine metal complex containing piperazine ethyoxyl modification group is characterized in that the phthalocyanine metal complex has amphipathy and absorbs and sends spectrums to the wavelength position where the spectrums can pierce through human tissues in red shift mode, and photosensitizer is high in reactive oxygen production capacity. The preparing method is simple and has remarkable economic effect and social effect.

Description

technical field [0001] The invention belongs to the field of preparation of photodynamic drugs or photosensitizers, and in particular relates to a phthalocyanine metal complex containing a piperazine ethoxy modification group and a preparation method thereof. Background technique [0002] Phthalocyanine complexes are an important class of functional materials, and have important applications in the fields of dyes, optical recording media, nonlinear optical materials, catalysts, etc. Among them, phthalocyanine complexes are used as photosensitizers in Photodynamic Therapy (Photodynamic Therapy) The prospects are compelling. [0003] The so-called photodynamic therapy (or photodynamic therapy), in essence, is the application of the photosensitization reaction of photosensitizers (or photosensitizers) in the medical field. The process of action is to first inject the photosensitizer into the body, and after a period of time (this waiting time is to allow the drug to be relativ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K41/00A61K31/409A61P35/00A61P31/10A61P31/04
Inventor 黄剑东张洪鹏冬梅
Owner FUZHOU UNIV
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