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Camptothecin phospholipid compound, and medicinal composition and application thereof

A technology of phospholipid compound and camptothecin, which is applied in the field of medicine and can solve the problems of leakage of drugs and difficulty in exerting efficacy of drugs.

Active Publication Date: 2015-01-28
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the fluidity of the liposome membrane, the drug is easy to leak out, making it difficult for the encapsulated drug to exert a good drug effect

Method used

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  • Camptothecin phospholipid compound, and medicinal composition and application thereof
  • Camptothecin phospholipid compound, and medicinal composition and application thereof
  • Camptothecin phospholipid compound, and medicinal composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0124] The synthesis of camptothecin-20-phospholipid compound (synthetic route sees figure 1 )

[0125] Take 1g of camptothecin, 0.75g of succinic anhydride, 0.2g of DMAP, and 0.2g of triethylamine, add dichloromethane or chloroform as the reaction solvent, add reflux reaction, and react for 12h; wash with dilute hydrochloric acid three times, filter dilute hydrochloric acid layer, take the filter cake; add methanol to dissolve, place at 4°C for 12h, filter, take the filter cake, and dry to obtain the intermediate camptothecin-20-succinic acid monoester.

[0126] Take 0.5g of the intermediate camptothecin succinate monoester, add 0.5g of CDI, add dichloromethane, chloroform or DMSO as the reaction solvent, add 0.5g of GPC and 0.5g of DBU to react at room temperature, and the resulting reaction solution passes through the column layer Analysis and purification yielded 0.32 g of the product camptothecin-20-phospholipid compound. 1 H NMR (500MHz, CD3OD:CDCl 3 1:1):δ8.03-7.59(1...

Embodiment 2

[0128] The synthesis of camptothecin-20-acetate-10-phospholipid compound (synthetic route sees figure 2 )

[0129] 0.5g of 10-hydroxycamptothecin, 1g of acetic acid, 1g of EDCI, 0.5g of HOBT, add dichloromethane or chloroform as the reaction solvent, react at 40°C for 12h; wash with dilute hydrochloric acid three times, filter the dilute hydrochloric acid layer, and take the filter cake Add methanol to dissolve, place at 4°C for 12h, filter, take the filter cake, and dry to obtain 10-hydroxycamptothecin-20-acetate.

[0130] 0.3g of 10-hydroxycamptothecin-20-acetate, 1g of succinic anhydride, 0.5g of DMAP, 0.5g of triethylamine, add dichloromethane or chloroform as the reaction solvent, add reflux reaction, and react for 12h; dilute Wash with hydrochloric acid three times, filter the dilute hydrochloric acid layer, and take the filter cake; add methanol to dissolve, place at 4°C for 12 hours, filter, take the filter cake, and dry to obtain the intermediate product camptotheci...

Embodiment 3

[0133] Synthesis of 7-ethyl-camptothecin-20-acetate-10-phospholipid compound

[0134] 0.5g of 7-ethyl-10-hydroxycamptothecin, 1g of acetic acid, 1g of EDCI, 0.5g of HOBT, add dichloromethane or chloroform as the reaction solvent, react at 40°C for 12h; wash with dilute hydrochloric acid three times, filter dilute hydrochloric acid layer, take the filter cake; add methanol to dissolve, place at 4°C for 12h, filter, take the filter cake, and dry to obtain 7-ethyl-10-hydroxycamptothecin-20-acetate.

[0135] 0.35g of 7-ethyl-10-hydroxycamptothecin-20-acetate, 1g of succinic anhydride, 0.5g of DMAP, 0.5g of triethylamine, add dichloromethane or chloroform as the reaction solvent, add reflux reaction , reacted for 12h; washed with dilute hydrochloric acid three times, filtered the dilute hydrochloric acid layer, and took the filter cake; added methanol to dissolve, placed at 4°C for 12h, filtered, took the filter cake, and dried to obtain the intermediate product 7-ethyl-camptotheci...

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Abstract

The invention discloses a camptothecin phospholipid compound, and a preparation method, a medicinal composition and a use thereof. The medicinal composition is a camptothecin phospholipid compound or a combined medicinal composition composed of the camptothecin phospholipid compound and a pharmacodynamically acceptable carrier, and can be a liquid preparation, a solid preparation, a semisolid preparation, a capsule, a granule, a gel or an injection. The medicinal composition is camptothecin phospholipid compound or a liposome nanoparticle prepared by using the camptothecin phospholipid compound and an assistant, and the particle size of the nanoparticle is 10-1000nm. The camptothecin phospholipid compound and its liposome nanoparticle can be used as a liquid preparation, a solid preparation, a semisolid preparation, a sterilized preparation or an aseptic preparation, have low toxicity, and can be used for efficient treatment of various tumors.

Description

technical field [0001] The invention relates to a camptothecin-like phospholipid compound with antitumor effect, its pharmaceutical composition and application, and relates to the technical field of medicine. Background technique [0002] Camptothecin (CPT) is an alkaloid with strong cytotoxic activity and can be used to treat various malignant tumors, such as gastric cancer, liver cancer, bladder cancer and leukemia. Scientists have discovered the unique anti-cancer mechanism of camptothecin compounds: by forming a stable triplet complex of camptothecin-topoisomerase I-DNA, the DNA double helix structure cannot be replicated after being broken. Camptothecin compounds are the most classic specific inhibitors of Topo I. Topo I has become one of the most popular targets for designing new anticancer drugs. Topo I inhibitors are listed as one of the six major categories of anti-tumor drugs by the National Cancer Institute (NCI) Drug Mechanism Analysis Network System. [0003]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/127A61K31/4745A61K47/48A61K47/24A61P35/00
CPCA61K9/127A61K31/4745C07D491/22
Inventor 李新松方硕
Owner SOUTHEAST UNIV
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