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COX-2 enzyme targeting phthalocyanine indometacin complex as well as preparation method and application thereof

A technology of COX-2 and indomethacin, which is applied in the direction of medical preparations with non-active ingredients, medical preparations containing active ingredients, and pharmaceutical formulas, can solve the problem of reducing the effect of photodynamic therapy, reducing the degree of phthalocyanine aggregation, Affect singlet oxygen and other issues to achieve the effect of increasing singlet oxygen production rate, reducing aggregation degree, and enhancing uptake

Inactive Publication Date: 2021-01-12
FUZHOU UNIV
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  • Application Information

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Problems solved by technology

The photosensitizers used in photodynamic therapy are mainly porphyrin and phthalocyanine. Phthalocyanine is a macrocyclic planar structure, which is easy to aggregate by itself, especially in aqueous solution, which is easy to form dimers or polymers. Seriously affect its ability to generate singlet oxygen and reduce the effect of photodynamic therapy, so reducing the degree of phthalocyanine aggregation is an urgent problem to be solved
In recent years, researchers have reduced the aggregation of phthalocyanine by introducing some functional groups with large steric hindrance in the axial direction of phthalocyanine or in the α and β positions of phthalocyanine. This method has low targeting

Method used

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  • COX-2 enzyme targeting phthalocyanine indometacin complex as well as preparation method and application thereof
  • COX-2 enzyme targeting phthalocyanine indometacin complex as well as preparation method and application thereof
  • COX-2 enzyme targeting phthalocyanine indometacin complex as well as preparation method and application thereof

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Embodiment Y

[0025] The preparation of embodiment Yd-ZnPc-3

[0026] With 3-nitrophthalonitrile as the original raw material, 3-(4-carboxymethylphenoxy)phthalonitrile is obtained through nucleophilic reaction, and then 1-(4- Carboxyphenoxy) zinc phthalocyanine, and then through the nucleophilic substitution reaction between 1-(4-carboxyphenoxy) zinc phthalocyanine, hexamethylenediamine, and indomethacin active ester to generate the target product of Yd-Pc.

[0027] Specific steps are as follows:

[0028] 1) Mix 2.00g (11.6mmol) 3-nitrophthalamide, 1.757g (11.6mmol) methyl p-hydroxybenzoate, 3.202g (23.2mmol) K 2 CO 3 Dissolved in 20 ml of DMF, reacted at room temperature for 24 hours, added 100 ml of water to the reaction solution to precipitate a white precipitate, filtered and dried to obtain 2.5 g of compound 1a with a yield of 78%. 1 H NMR (400 MHz, Chloroform- d ) δ 8.13 (d, J = 8.2 Hz, 2H), 7.64 (t, J = 8.2 Hz, 1H), 7.54 (d, J = 7.7 Hz, 1H), 7.16 (dd, J = 17.6, 8.2 Hz, 3H...

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Abstract

The invention discloses a COX-2 enzyme targeting phthalocyanine indometacin complex as well as a preparation method and application thereof, and the preparation method comprises the following steps: by taking 3-nitro phthalonitrile as an original raw material, carrying out nucleophilic reaction to obtain 3-(4-carboxyl methyl ester phenoxy) phthalonitrile, carrying out cyclization reaction and nucleophilic reaction to generate 1-(4-carboxyl phenoxy) phthalocyanine, and finally, generating a target product (M=Al or Zn, and n=an integer of 1-3) through nucleophilic substitution reaction. The complex can reduce the aggregation effect of the photosensitizer phthalocyanine and improve the killing effect of the photosensitizer on tumor cells, and a new thought is provided for improving photodynamic therapy.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a phthalocyanine-indomethacin complex targeting COX-2 enzyme, a preparation method and application thereof. Background technique [0002] Cancer is a major disease that endangers human health. Currently, cancer treatment methods include chemotherapy, radiotherapy, surgical resection, and photodynamic therapy, among which photodynamic therapy has great potential because of its selectivity, minimal invasiveness, and low toxicity. The photosensitizers used in photodynamic therapy are mainly porphyrin and phthalocyanine. Phthalocyanine is a macrocyclic planar structure, which is easy to aggregate by itself, especially in aqueous solution, which is easy to form dimers or polymers. Seriously affect its ability to generate singlet oxygen and reduce the effect of photodynamic therapy, so reducing the degree of phthalocyanine aggregation is an urgent problem to be solved. ...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K41/00A61K47/55A61P35/00
CPCA61K41/0076A61K47/55A61P35/00C07D487/22
Inventor 陈涓涓薛金萍黄坤山
Owner FUZHOU UNIV
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