Zinc(II) carboxyl phthalocyanine and adriamycin conjugate and preparation and application thereof

A technology of zinc phthalocyanine and doxorubicin, which is applied in the field of carboxyzinc phthalocyanine-doxorubicin conjugates and their preparation and application, which can solve the problems of lack of efficient combination drugs, clinical application limitations, and high skin phototoxicity. problem, to achieve the effect of good clinical application prospect, good stability and high photosensitization ability

Active Publication Date: 2016-06-01
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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, there is still a lack of highly effective combination drugs, especially those with targeted functions

Method used

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  • Zinc(II) carboxyl phthalocyanine and adriamycin conjugate and preparation and application thereof
  • Zinc(II) carboxyl phthalocyanine and adriamycin conjugate and preparation and application thereof
  • Zinc(II) carboxyl phthalocyanine and adriamycin conjugate and preparation and application thereof

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preparation example Construction

[0029] The preparation method of carboxyl phthalocyanine zinc-doxorubicin conjugate comprises the following steps:

[0030] With zinc phthalocyanine and doxorubicin hydrochloride as reactants, N, N-dimethylformamide as solvent, in 1-ethyl-(3-dimethylaminopropyl) carbodiimide In the presence of hydrochloride, 1-hydroxybenzotriazole, 4-dimethylaminopyridine and under the protection of nitrogen, continue to stir and react at room temperature -35°C for 8-24h, and then purify by extraction method or solvent method, and column chromatography Carboxyzinc phthalocyanine-doxorubicin conjugate;

[0031] In the above reaction, the molar ratio of carboxyl zinc phthalocyanine and doxorubicin hydrochloride is 1:1-2; 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride, The amount of 1-hydroxybenzotriazole and 4-dimethylaminopyridine is 1-3 mmol per mmol of carboxyzinc phthalocyanine; the amount of solvent is 5-10 mL.

[0032] The carboxyl phthalocyanine zinc of the present invention...

Embodiment 1

[0048] Compound (1), namely 1-(3-carboxyphenoxy)zinc phthalocyanine represented by formula (1):

[0049] ;

[0050] (1)

[0051] The preparation method comprises the following steps:

[0052] (1) Prepare 3-(3-carboxyphenoxy)phthalonitrile with the following structure: ;

[0053] Take 3-hydroxybenzoic acid (15mmol) and 3-nitrophthalonitrile (15mmol) as reactants, anhydrous DMSO as solvent (30ml), in the presence of potassium carbonate (45mmol) and nitrogen protection, stir at room temperature The reaction was carried out for 30 hours, and the end point of the reaction was monitored by thin layer chromatography. The reaction mixture was suction-filtered with a sand core funnel, the filtrate was collected, and the filtrate was added to 500ml of ice-water mixture, adjusted with 1M hydrochloric acid solution until the solution was acidic, and a large amount of precipitate was precipitated, left to stand, and washed repeatedly with a microporous organic filter membrane. The ...

Embodiment 2

[0059] Compound (2), namely 1-(4-carboxyphenoxy)zinc phthalocyanine represented by formula (2):

[0060] ;

[0061] (2)

[0062] The preparation method comprises the following steps:

[0063] (1) Prepare 3-(4-carboxyphenoxy)phthalonitrile with the following structure: ;

[0064] With p-hydroxybenzoic acid (15mmol) and 3-nitrophthalonitrile (15mmol) as reactants, with anhydrous DMSO as solvent (30ml), in the presence of potassium carbonate (45mmol) and under the protection of nitrogen, the reaction was stirred at room temperature At 30 hours, the reaction endpoint was monitored by thin layer chromatography. The reaction mixture was suction-filtered with a sand core funnel, the filtrate was collected, and the filtrate was added to 500ml of ice-water mixture, adjusted with 1M hydrochloric acid solution until the solution was acidic, and a large amount of precipitate was precipitated, left to stand, and washed repeatedly with a microporous organic filter membrane. The next...

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Abstract

The invention discloses a zinc(II) carboxyl phthalocyanine and adriamycin conjugate and preparation and application thereof, and belongs to the field of photosensitizer and drug preparation. A structural formula of the zinc(II) carboxyl phthalocyanine and adriamycin conjugate is (I) or (II) or (III) or (IV) shown in the description. The compound is a novel photosensitive drug and an anti-cancer drug which has the double effects of a photodynamic therapy and chemotherapy. Meanwhile, the product composition is single, the structure is definite, and the preparation technology is simple.

Description

technical field [0001] The invention belongs to the field of medicine preparation, and in particular relates to carboxyl phthalocyanine zinc-doxorubicin conjugate and its preparation and application. Background technique [0002] 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 in the target body), the target body is irradiated with light of a specific wavelength (for the target in the body cavity, optical fiber can be used to Under the light excitation, the photosensitizer enriched in the target body inspires a series of photophysical and photochemical reactions to generate reactive oxygen species, thereby destroying the target body (such as cancer cells and cancer tissues). The k...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/252C07H1/00A61K41/00A61K47/48A61K31/7135A61P35/00A61P35/02A61P31/04A61P1/02A61P27/02A61P9/10A61P17/00A61P31/12A01N43/90A01P1/00
CPCA01N43/90A61K41/0071C07H1/00C07H15/252
Inventor 黄剑东陈星伟郑巧凤柯美荣
Owner FUZHOU UNIV
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