Application of gossypol derivative to preparing anti-tumor medicament

A technology for drugs and tumors, applied in the field of biomedicine, can solve the problems of non-drugs and poor water solubility of Apogossypol

Inactive Publication Date: 2012-01-11
SHANGHAI ADVANCED RES INST CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the poor water solubility of Apogossypol indicates that it is not a very suitable drug and needs further improvement

Method used

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  • Application of gossypol derivative to preparing anti-tumor medicament
  • Application of gossypol derivative to preparing anti-tumor medicament
  • Application of gossypol derivative to preparing anti-tumor medicament

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0086] 1. Compound Preparation

[0087] A general procedure for the preparation of the compounds can be found in figure 1 , the method description is as follows:

[0088] Preparation of 6-APA-Na-vassinone (Compound 7)

[0089]Take 39 mg of 6-APA (6-aminopenicillin alkanoic acid), 10 mg of sodium hydroxide, dissolve in 6 ml of methanol and isopropanol [1:1 (v / v)] at 0 degrees Celsius, and detect when the pH is close to 6 , 48 mg of cottonone was added, kept at room temperature for 5 hours, filtered with suction, rinsed with isopropanol, and dried to obtain 64 mg of compound 7.

[0090] Compound 7

[0091] 1 H NMR (300MHz, CD 3 OD) δ9.54(s, 2H), 9.53(s, 2H), 5.65(d, J=6Hz, 2H), 5.66(d, J=5.7Hz, 2H), 5.44-5.46(m, 4H) , 4.28 (br s, OH), 4.25 (br s, OH), 3.99 (m, 4H), 1.96 (s, 6H), 1.98 (s, 6H), 1.66 (s, 6H), 1.66 (s, 6H) , 1.59(s, 12H), 1.44(d, J=6.9Hz, 12H), 1.43(d, J=7.2Hz, 12H); 13 C NMR (75MHz, CDCl 3 )δ187.3, 187.3, 185.4, 185.3, 172.8, 171.2, 171.1, 167.4, 167.2, ...

Embodiment 1

[0135] Example 1. Cell Viability Detection

[0136] The inventors first detected the newly synthesized compound ( figure 1 , compound 3-9; wherein compound 8 is an optical racemate, compound 9 is a positive optical compound) killing effect on different tumor cell lines. After some human and mouse tumor cell lines were treated with different concentrations of compounds for 72 hours, cell viability was detected by MTT assay.

[0137] The results showed that compounds 3-9 all had a certain killing effect on tumor cells, especially compound 7. Human and mouse colon cancer cell lines SW620, HCT116 and CT26 are sensitive to compound 7, the median lethal dose IC 50 Approximately 6 to 18 μM (Table 1). Breast cancer cell lines MDA-MB-435, MCF-7 and 4T1 are also sensitive to compound 7, IC 50 Values ​​over 28 μM. Compound 7 also had obvious killing effects on mouse melanoma cell line B16-F10, human lung cancer cell line A549 and prostate cancer cell line PC-3 (Table 1). These resu...

Embodiment 2

[0141] Example 2. Compound 7 induces apoptosis of CT26 cells

[0142] The present inventors treated CT26 cells with different concentrations of compound 7 for 24, 48 or 72 hours, and detected the apoptosis rate of tumor cells by TUNEL kit ( figure 2 B). See TUNEL statistical results figure 2 c.

[0143] The above results show that compound 7 can induce tumor cell apoptosis, and the induction of tumor cell apoptosis has time- and dose-dependent effects.

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Abstract

The invention relates to application of a gossypol derivative to preparing an anti-tumor medicament and discloses a novel gossypol derivative, use of the derivative for preparing a medicinal composition for preventing and treat tumors, and the medicinal composition comprising the gossypol derivative and a preparation method thereof.

Description

technical field [0001] The invention belongs to the field of biomedicine; more specifically, the invention relates to the application of gossypol derivatives in the preparation of antitumor drugs. Background technique [0002] Malignant tumors are a serious threat to human health. Traditional chemotherapy and radiotherapy lack specificity, and while achieving curative effects, they often bring serious side effects to patients. [0003] Colorectal cancer is the third most common type of cancer and the third leading cause of death in the United States. In 2009, there were approximately 146,970 new cases of colon cancer in the United States, of which 49,920 died. The 5-year survival rate of patients with non-metastatic colon cancer is about 90%, but it drops to 68% after the occurrence of regional metastasis (such as lymph node metastasis), and only 10% after the occurrence of distant metastasis. Current clinical strategies for the treatment of colon cancer include surgical r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D499/21C07C251/24C07D209/20A61K31/431A61K31/195A61K31/405A61K31/04A61K31/513A61P35/00C07D499/16C07D499/10C07C249/02
CPCC07D499/10A61K31/405C07D209/20A61K31/04C07D499/16A61K31/431A61K31/513C07D499/21C07C251/24A61K31/195A61P35/00
Inventor 郭方姜标
Owner SHANGHAI ADVANCED RES INST CHINESE ACADEMY OF SCI
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