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A kind of octasulfonic acid phthalocyanine and its preparation method and application

A technology of octasulfonic acid group and disulfonic acid group, which is applied in the field of octasulfonic acid group-substituted phthalocyanine metal complexes and its preparation, can solve problems such as poor biological selectivity, poor stability, and complicated synthetic routes, and achieve Effects of high photodynamic anticancer activity, large molar absorption coefficient, and high photosensitivity activity

Active Publication Date: 2015-08-12
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the currently reported biologically active phthalocyanine complexes still have deficiencies, such as lack of amphiphilicity, poor stability, complex synthetic routes, poor bioselectivity, or easy aggregation in aqueous solution, etc. , needs to be further improved

Method used

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  • A kind of octasulfonic acid phthalocyanine and its preparation method and application
  • A kind of octasulfonic acid phthalocyanine and its preparation method and application
  • A kind of octasulfonic acid phthalocyanine and its preparation method and application

Examples

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preparation example Construction

[0036] In the present invention, the preparation method of tetra-a-(6,8-sodium disulfonate base-2-naphthyloxy) phthalocyanine metal complex comprises the following steps:

[0037] (1) Preparation of 3-(6,8-disulfonic acid-2-naphthyloxy) phthalonitrile dipotassium salt: 3-nitrophthalonitrile and 2-naphthol-6,8-di Dipotassium sulfonate was used as a reactant, dimethyl sulfoxide was used as a solvent, in the presence of potassium carbonate and under the protection of nitrogen, the reaction was stirred at room temperature ~45°C for 48~96 hours, monitored by thin layer chromatography, when 3-nitro-o When phthalonitrile is basically consumed, the reaction is terminated, and the target product is purified by solvent method, recrystallization method and extraction method; in the above reaction, 3-nitrophthalonitrile and 2-naphthol-6,8-disulfonic acid disulfide The molar ratio of potassium is 1:1 ~ 1.5, the solvent consumption is that every mmol reactant 3-nitrophthalonitrile needs 2 ~...

Embodiment 1

[0051] Synthesis and Physicochemical Properties of 1,8(11), 15(18), 22(25)-tetrakis(6,8-disulfonic acid sodium-2-naphthyloxy)zinc phthalocyanine

[0052]

[0053] Formula 1)

[0054] This compound can also be called tetra-a-(6,8-sodium disulfonate-2-naphthyloxy)zinc phthalocyanine, and its structure is shown in formula (1), wherein:

[0055] .

[0056] (1) Preparation of 3-(6,8-disulfonic acid-2-naphthyloxy) phthalonitrile dipotassium salt: with 3-nitrophthalonitrile (5 mmol) and 2-naphthol-6, Dipotassium 8-disulfonate (5~7.5mmol, preferably 5mmol) was used as reactant, dimethyl sulfoxide (10~25mL, preferably 10mL) was used as solvent, in potassium carbonate (7.5~15mmol, preferably 10mmol), divided into three In the presence of batch addition) and nitrogen protection, the reaction was stirred at room temperature to 60°C (preferably 45°C) for 48 to 96 hours, monitored by thin-layer chromatography, and the reaction was terminated when 3-nitrophthalonitrile was basically c...

Embodiment 2

[0061] Synthesis of 2(3), 9(10), 16(17), 23(24)-tetrakis(6,8-disulfonate sodium-2-naphthyloxy)zinc phthalocyanine

[0062]

[0063] Formula (2)

[0064] This compound can also be called tetrakis-b-(6,8-sodium disulfonate-2-naphthyloxy)zinc phthalocyanine, and its structure is shown in formula (2), wherein:

[0065]

[0066] Substituting equimolar 4-nitrophthalonitrile for 3-nitrophthalonitrile in Example 1, the corresponding peripheral octasulfonic acid group substituted phthalocyanine metal complexes, i.e. four-beta- Zinc (6,8-sodium disulfonate-2-naphthyloxy)phthalocyanine. The structure of the obtained product is the same as that of the phthalocyanine product described in Example 1, except that the position of the substituent is replaced by the β position.

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Abstract

The invention discloses an octa-sulfonic phthalocyanine metal complex, and a preparation method and application thereof, and belongs to photosensitizers, photodynamic medicines or photosensitive agents. The compound disclosed by the invention has the characteristics of high photosensitive activity and high water solubility; the compound exists in water in the form of monomers and is favorable to play the photodynamic activity in a water body; the absorption spectroscopy is red-shifted to a near infrared area which facilitates the penetration of human tissues.

Description

technical field [0001] The invention belongs to the field of preparation of photodynamic drugs or photosensitizers, and in particular relates to an octasulfonic acid group-substituted phthalocyanine metal complex and its preparation method and application. 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, the application prospects of phthalocyanine complexes as photosensitizers are attracting attention. [0003] Photosensitizers can be used for photodynamic therapy (Photodynamic Therapy) of tumors or other non-cancerous diseases, and photosensitizers used for photodynamic therapy can be called photodynamic drugs or photosensitizers. [0004] The so-called photodynamic therapy (or photodynamic therapy), in essence, is the application of the photosensitization reaction of photosensitizers (...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22A61K41/00A61P35/00A61P31/04A61P1/02A61P27/02A61P9/10A61P17/02A61P17/00A61P31/12A61P7/00A01N43/90A01P1/00C02F1/30C02F1/50
CPCA01N43/90A61K41/0071C02F1/30C02F1/505C07D487/22
Inventor 黄剑东李兴淑柯美荣唐庆庆
Owner FUZHOU UNIV
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