PH sensitivity type anticancer prodrug as well as preparation method and application thereof

An anti-cancer drug and sensitive technology, applied in the field of medicine and chemical industry, can solve the problems of reducing the therapeutic effect of doxorubicin, reducing the solubility, toxic and side effects, etc., and achieving the effect of good phagocytosis, small particle size and narrow distribution

Active Publication Date: 2009-05-20
SICHUAN YINGRUI PHARMA TECH CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Pectin is soluble in water at pH 6-8, but as the pH decreases, the solubility will decrease
[0004] Pectin-doxorubicin conjugates are suitable for the preparation of lymphatic-targeted drugs, liver-targeted drugs or lung-targeted drugs, but if pectin-doxorubicin conjugates circulate in the blood (pH≈7.4), they are still Doxorubicin has been released before reaching the cancer entity, which will cause toxic side effects and reduce the therapeutic effect of doxorubicin

Method used

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  • PH sensitivity type anticancer prodrug as well as preparation method and application thereof
  • PH sensitivity type anticancer prodrug as well as preparation method and application thereof
  • PH sensitivity type anticancer prodrug as well as preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0028] Embodiment 1 Preparation of pectin-doxorubicin conjugate of the present invention

[0029] Weigh 1g of pectin (molecular weight 71,000-400,000, average molecular weight 200,000), add 100ml of water, after the pectin is dissolved, adjust the pH to 6-8 with sodium hydroxide solution. Dissolve 0.5 g of doxorubicin hydrochloride in 100 ml of water, transfer to the pectin solution, control the temperature at 50° C., and stir for 30 minutes. 1 g of EDC·HCl was added, the temperature was controlled at 50° C., and the reaction was stirred for 6.5 hours. After reaching the required time, it was transferred to a dialysis bag with a molecular weight cut off of 7000, dialyzed with secondary water for 24 hours, and the dialyzate was concentrated to dryness to obtain 0.9 g of a red solid.

Embodiment 2

[0030] Embodiment 2 Preparation of pectin-doxorubicin conjugate of the present invention

[0031] Weigh 1g of pectin (molecular weight 71,000-400,000, average molecular weight 200,000), add 100ml of water, after the pectin is dissolved, adjust the pH to 6-8 with sodium hydroxide solution. Dissolve 0.5 g of doxorubicin hydrochloride in 100 ml of water, transfer to the pectin solution, control the temperature at 50° C., and stir for 30 minutes. 1 g of EDC·HCl was added, the temperature was controlled at 50° C., and the reaction was stirred for 8 hours. After reaching the required time, it was transferred to a dialysis bag with a molecular weight cut off of 7000, dialyzed with secondary water for 24 hours, and the dialyzate was concentrated to dryness to obtain 1.1 g of a red solid.

Embodiment 3

[0032] Example 3 Preparation of Pectin-Adriamycin Conjugate of the Present Invention

[0033] Weigh 1g of pectin (molecular weight 71,000-400,000, average molecular weight 200,000), add 100ml of water, after the pectin is dissolved, adjust the pH to 6-8 with sodium hydroxide solution. Dissolve 0.5 g of doxorubicin hydrochloride in 100 ml of water, transfer to the pectin solution, control the temperature at 30° C., and stir for 30 minutes. 1 g of EDC·HCl was added, the temperature was controlled at 30°C, and the reaction was stirred for 24 hours. After reaching the required time, it was transferred to a dialysis bag with a molecular weight cut off of 7000, dialyzed with secondary water for 24 hours, and the dialyzate was concentrated to dryness to obtain 1 g of a red solid.

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Abstract

The invention relates to a pH-sensitive anticancer prodrug and a preparation method as well as application thereof, which belongs to the field of medicine and chemical industry. The technical problem to be solved is to provide the pH-sensitive anticancer prodrug, and the anticancer prodrug has highest solubility when the pH value is between 4 and 6, can nearly not be dissolved when the pH value is less than 3 or more than 7, and almost does not release adriamycin during the circulation due to small solubility particularly when circulating in blood (the pH value is approximately equal to 7.4), thereby having small toxic side effect. The pH-sensitive anticancer prodrug is a conjugate obtained by coupling the adriamycin and pectin with a molecular weight of between 71,000 and 400,000 through a chemical bond. The pH-sensitive anticancer prodrug is obtained by the following steps: a pectin aqueous solution and an adriamycin aqueous solution are added with a dehydrating agent to react under the condition that the pH value is between 6 and 8, and then are dialyzed and condensed.

Description

technical field [0001] The invention relates to a pH-sensitive anticancer prodrug and its preparation method and application, belonging to the field of medicine and chemical industry. Background technique [0002] In recent years, macromolecular targeted anticancer drugs have become the focus of research on chemotherapy drugs for lymphatic metastasis. Such conjugates have a large molecular volume and cannot enter the blood through the very narrow endothelial space of capillaries after local injection. , and it is easier to enter the local draining lymph nodes through the wider endothelial gap of the lymphatic capillaries. In addition, such conjugates can also be taken to local lymph nodes by being phagocytized by macrophages, and under the action of enzymes in lymph nodes, they are hydrolyzed to release active substances (anticancer drugs) to kill lymph node metastasis. The role of cancer cells. Therefore, this kind of macromolecule carrier-targeted drug is most suitable f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/48A61K31/704A61P35/00A61K47/61
Inventor 唐小海谢永美宋鑫邱宇
Owner SICHUAN YINGRUI PHARMA TECH CO
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