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Galactose-containing platinum complex for tumour targeted therapy and preparation method thereof

A technology of tumor targeting and platinum complexes, which is applied in the preparation of sugar derivatives, medical preparations containing active ingredients, sugar derivatives, etc., which can solve the problems of increasing toxic side effects, difficult renal elimination, and lack of tumor targeting function of drugs and other problems, to achieve the effect of high water solubility and clinical application of tumor targets

Inactive Publication Date: 2011-12-14
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] One of the main reasons for the above-mentioned fatal flaws of platinum-based anticancer drugs is that the drugs themselves lack the targeting function against tumors.
In addition, the low water solubility of the drug also causes the drug to stay in the blood for too long and is difficult to be eliminated by the kidneys.

Method used

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  • Galactose-containing platinum complex for tumour targeted therapy and preparation method thereof
  • Galactose-containing platinum complex for tumour targeted therapy and preparation method thereof
  • Galactose-containing platinum complex for tumour targeted therapy and preparation method thereof

Examples

Experimental program
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preparation example Construction

[0049] The specific preparation can be accomplished using the following methods and reaction formulas.

[0050] Method A:

[0051]

[0052] Method B:

[0053]

[0054] In method A, when M is a hydrogen atom in formula (III), the reaction can be carried out by using an appropriate inorganic base, such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, lithium hydroxide and hydrogen cesium oxide etc. to adjust the pH of the reaction aqueous solution and maintain between 7-9 to complete the preparation of the compound shown in formula (I); when M is a metal atom, for example: sodium atom, potassium atom, lithium atom, barium atom or cesium Atoms, the reaction can be carried out smoothly directly in the aqueous solution, and if necessary, use a small amount of the aqueous solution of the above-mentioned inorganic base to maintain the pH of the reaction solution between 7-9 to complete the synthesis of the complex shown in fo...

Embodiment 1

[0076] (1) Preparation of 1-O-D-galactoside-2-bromo-ethane:

[0077]

[0078] 1) Add galactose (2.7g, 15mmol) to 2-bromoethanol (10ml) at room temperature, cool to 0°C, replace the air in the flask with nitrogen, and slowly add boron trifluoride dropwise under nitrogen protection Ether solution (98%, 1 ml).

[0079] 2) Stir the reaction solution at 0°C for 15 minutes, then slowly warm up to room temperature and stir for 30 minutes, then heat the reaction solution to 80°C, and react at 80°C for 5 hours.

[0080] After the reaction was completed, the solvent was removed by rotary evaporation, and the reaction product was simply purified by silica gel column chromatography (dichloromethane:methanol, 6:1) to obtain 2.4 g of a crude product.

[0081] Mass spectrum: MS, m / z: 287.03 [M+H] +

[0082] (2) Preparation of 1-O-(2,3,4,6-tetraacetyl-D-galactoside)-2-bromo-ethane:

[0083]

[0084] At room temperature, 2.4 g of the product 1-O-D-galactoside-2-bromo-ethane obtained ...

Embodiment 2

[0133] (1) Preparation of 1-O-D-galactoside-3-bromo-propane:

[0134]

[0135] Add galactose (1.8g) to 3-bromopropanol (10mL) at room temperature, cool to 0°C, replace the air in the flask with nitrogen, and slowly drop in the ether solution of boron trifluoride under the protection of nitrogen (98%, 1 mL). The reaction solution was stirred at 0°C for 15 minutes, raised to room temperature and stirred for 30 minutes, then heated to 80°C, and reacted at 80°C for 5 hours. After the reaction was completed, the solvent was removed by rotary evaporation, and 2.05 g of crude product was obtained after simple purification by silica gel column chromatography (dichloromethane:methanol, volume ratio 6:1).

[0136] Mass spectrum: MS, m / z: 301.03 [M+H] +

[0137] (2) Preparation of 1-O-(2,3,4,6-tetraacetyl-D-galactoside)-3-bromo-propane:

[0138]

[0139] At room temperature, 2.05 g of the crude product of 1-O-D-galactoside-3-bromo-propane obtained in the previous step was disso...

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Abstract

The invention discloses a galactose-containing platinum complex for tumor targeted therapy and a preparation method thereof; the complex is shown in formula (I); and experiment demonstrates that the complex of the invention and medicaments prepared by the complex of the invention have high water solubility, have tumor target effect, and is convenient for clinical application.

Description

technical field [0001] The invention relates to a platinum complex, in particular to a galactose-containing platinum complex for tumor targeting therapy and a preparation method thereof. Background technique [0002] The reason why tumors have become a disease that is difficult to cure in medicine is mainly because it is difficult for drug treatment to distinguish cancer cells from normal cells. Drugs that are generally lethal to cancer cells are also toxic to normal cells. How to accurately and scientifically find the difference between cancer cells and normal cells, and how to target, selectively control and kill cancer cells is one of the keys to fundamentally solve and cure this disease that threatens human health. [0003] Platinum anticancer drugs are a representative class of drugs in the field of tumor treatment. It belongs to cell cycle non-specific drugs and has therapeutic effects on sarcoma, malignant epithelial tumors, lymphomas and germ cell tumors. At prese...

Claims

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Application Information

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IPC IPC(8): C07H23/00C07H1/00A61K31/7135A61P35/00
Inventor 鲁彦会刘朋兴陈惠渝高清志
Owner TIANJIN UNIV
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