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Application of phthalocyanine metal complex containing piperazine ethyoxyl modified groups

A technology of metal complexes and ethoxylates, which is applied in the directions of medical preparations, drug combinations, and pharmaceutical formulations containing active ingredients, can solve the problems of poor biological selectivity, limited clinical application, unstable composition, etc. Fungal cell and cancer cell uptake rate, enhanced photodynamic activity, and effect of large molar absorption coefficient

Active Publication Date: 2014-09-10
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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  • Application of phthalocyanine metal complex containing piperazine ethyoxyl modified groups
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  • Application of phthalocyanine metal complex containing piperazine ethyoxyl modified groups

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Synthesis and Physicochemical Properties of 1,8(11), 15(18), 22(25)-tetrakis[2-(N-tert-butoxycarbonylpiperazinyl)ethoxy]zinc phthalocyanine

[0040]

[0041] Formula 1)

[0042] This compound can also be called four-a-[2-(N-tert-butoxycarbonylpiperazinyl)ethoxy]zinc phthalocyanine, and its structure is shown in formula (1), wherein: .

[0043] (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 ...

Embodiment 2

[0049] Synthesis and Physicochemical Properties of 1,8(11), 15(18), 22(25)-Tetrakis(2-piperazinylethoxy)zinc Phthalocyanine

[0050] This compound can also be called four-a-(2-piperazinylethoxy)zinc phthalocyanine, and its structure is shown in formula (1), wherein: .

[0051] 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 the product ...

Embodiment 3

[0054] Synthesis and Physicochemical Properties of 1-[2-(N-tert-butoxycarbonylpiperazinyl)ethoxy]zinc Phthalocyanine

[0055]

[0056] Formula (2)

[0057] The structure of the compound is shown in formula (2), wherein: .

[0058] (1) Protect the terminal amino group of N-hydroxyethylpiperazine by BOC (tert-butoxycarbonyl): in 20~60ml (preferably 30 ml) CH 2 Cl 2Add 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 solvent was ...

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Abstract

The invention belongs to the field of preparation of photodynamic drugs or photosensitizers, and discloses the application of phthalocyanine metal complexes containing piperazine ethoxy modification groups, which can be used to prepare photodynamic drugs or photosensitizers. The phthalocyanine metal complexes of the invention The substance has the following characteristics: amphiphilic, the absorption spectrum is red-shifted to a wavelength that is more conducive to penetrating human tissue, and the ability to photosensitively generate active oxygen is high.

Description

technical field [0001] The invention belongs to the field of preparation of photodynamic drugs or photosensitizers, and in particular relates to the application of phthalocyanine metal complexes containing piperazine ethoxy modification groups. 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 relatively enriched i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22A61K41/00A61K31/496C02F1/30A61L2/18A61P1/02A61P9/10A61P17/00A61P27/02A61P31/04A61P31/10A61P31/12A61P35/00A61P35/02A61L101/44
Inventor 黄剑东郑碧远林滔
Owner FUZHOU UNIV
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