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Preparation method and application of hemoporphyrin/verapamil conjugates

A technology of methyl verapamil and hematoporphyrin, which is applied in the direction of medical preparations with non-active ingredients, medical preparations containing active ingredients, drug combinations, etc., can solve the problems of limited application and achieve the goal of improving physical and chemical properties Effect

Inactive Publication Date: 2021-04-27
范平生 +5
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is easily soluble in organic solvents but hardly soluble in water, so it cannot be directly administered intravenously, which greatly limits its clinical application

Method used

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  • Preparation method and application of hemoporphyrin/verapamil conjugates
  • Preparation method and application of hemoporphyrin/verapamil conjugates
  • Preparation method and application of hemoporphyrin/verapamil conjugates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of Hematoporphyrin / Verapamil Conjugate C2:

[0031] Dissolve 0.5mmol hematoporphyrin in a reaction vessel containing 50mL N,N′-diisopropylcarbodiimide (DIC), stir the reaction vessel on a magnetic stirrer, and then add 0.5mmol p-O - Desmethyl verapamil and 5 mmol 4-dimethylaminopyridine (DMAP), stirred at room temperature for 12 hours, and the progress of the reaction was detected by thin-plate chromatography (TLC).

[0032] After the reaction was completed, water was added for washing. After drying, the solvent was evaporated to obtain a crude reaction product. The crude product was dissolved in ethyl acetate, and silica gel equivalent to three times the mass of the crude product was added. The dark brown compound C2 was obtained by eluting with dichloromethane:methanol volume ratio 40:1 in silica gel column chromatography with a yield of 21%.

[0033] The results of the hydrogen spectrum and mass spectrum of the hematoporphyrin / verapamil conjugate C2 prep...

Embodiment 2

[0037] Activity Evaluation of Hematoporphyrin / Verapamil Conjugate C2

[0038] 1. Experimental equipment and materials: instrument ultra-clean bench (Sujing Group Antai Company), constant temperature incubator (Thermoelectron Corporation), microplate reader (BIO-RAD Company), inverted biological microscope (Chongqing Optical Instrument Factory); reagents: Cell culture medium RPMI-1640, DMEM (high glucose) (GIBCO company), fetal bovine serum (Hangzhou Sijiqing Co., Ltd.), tetramethylazolazolium blue (MTT) (Sigma company product), DMSO (Sigma company); Cell lines: human liver cancer cell lines HepG-2 and Bel-7402, human breast cancer cell line MCF-7, human prostate cancer cell line PC-3, and human colon cancer cell line HCT-116.

[0039] 2. Experimental method

[0040] 2.1 Cell inhibitory activity test method:

[0041] The above cells were stored at 37°C, 5% CO 2 Routine cultivation in a saturated humidity incubator. The culture medium is RPMI1640 cell culture medium containi...

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Abstract

The invention relates to the field of medicinal chemistry, in particular to preparation of hemoporphyrin / verapamil conjugates C1 and C2 and application of the hemoporphyrin / verapamil conjugates in preparation of anti-tumor drugs. Researches prove that the hemoporphyrin / verapamil conjugates disclosed by the invention can be used for remarkably inhibiting the activity of various tumor cells and achieving the treatment and control effects of resistant tumors.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to the preparation of a hematoporphyrin / verapamil conjugate C2 and its application in antitumor drugs. [0002] technical background [0003] Tumor multidrug resistance (MDR) is the cross-resistance of tumor cells to other anti-tumor drugs with the same or different structures, cell targets and mechanisms of action after they develop drug resistance to a chemotherapeutic drug. . Verapamil (VER) is a clinical calcium ion channel blocker widely used in heart disease. Experimental studies have shown that VER can significantly improve the sensitivity of malignant tumor cells to chemical drugs. As early as 1982, it was Studies have confirmed the reversal effect of verapamil on the MDR phenotype of tumor cells. Thereby reversing tumor cell MDR. However, the concentration of verapamil to effectively reverse tumor drug resistance is 6.0-10.0 μmol / L, but the intrave...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K47/55A61K31/277A61K41/00A61P35/00
CPCA61K31/277A61K41/0071A61K47/55A61P35/00A61K2300/00
Inventor 范平生李增纪丽君张腾跃汪国兴钱立庭刘亚贝杨广山黄金翁呈韬樊高飞汤丽莉王旭杨国红何静段巧虹刘淼吴旸赵永欣何义富王敏刘彤彤方平孙瑾
Owner 范平生
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