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Method for preparing water soluble pegylation hydroxycamptothecine derivatives

A technology of PEGylated hydroxycamptothecin and hydroxycamptothecin, applied to the preparation of water-soluble PEGylated hydroxycamptothecin derivatives, solid phosgene to prepare water-soluble PEGylated hydroxycamptothecin derivatives In the field of pharmaceuticals, it can solve the problems of rare PEGylation of hydroxycamptothecin, and achieve the effects of simple synthesis method, convenient storage, and broad market prospects

Inactive Publication Date: 2009-09-16
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent decades, some literatures have reported the PEGylation of CPT, but the PEGylation of hydroxycamptothecin (HCPT) is rare

Method used

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  • Method for preparing water soluble pegylation hydroxycamptothecine derivatives
  • Method for preparing water soluble pegylation hydroxycamptothecine derivatives
  • Method for preparing water soluble pegylation hydroxycamptothecine derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1. Preparation of water-soluble polyethylene glycol (PEG)-based hydroxycamptothecin (HCPT) derivatives

[0050] (1) Take by weighing 6.00g polyethylene glycol (PEG) 6000 and 0.36g hydroxycamptothecin (HCPT) and join in the round bottom flask that condensation tube, thermometer, constant pressure dropping funnel and magnetic stirring are housed, and measure Take 35mL of chloroform and pour it into it, seal it tightly, and stir it with magnetic force to completely dissolve the solid, and there is an anhydrous calcium chloride drying tube on the condensation tube.

[0051] (2) Pipette 2.9 mL of pyridine into the above mixture, stir and place in an ice-water bath.

[0052] (3) Weigh 1.78 g of solid phosgene and dissolve it in 5 mL of chloroform so that the concentration of solid phosgene is 1.2 mol / L, and quickly pour it into the dropping funnel. In an ice-water bath, the solid phosgene solution was slowly added dropwise to the above mixture, stirring rapidly wh...

Embodiment 2

[0057] As described in Example 1, the difference is that polyethylene glycol 4000 is used instead, and 4.00g is dropped into to obtain 3.70g of water-soluble polyethylene glycol (PEG)-based hydroxycamptothecin (HCPT) derivative solid product. It was 60.21%, and the weight average molecular weight was 22500.

Embodiment 3

[0059] As described in Example 1, the difference is that 1.09 g of hydroxycamptothecin (HCPT) is dropped into, and 3.56 g of BTC is dropped into to obtain 6.73 g of water-soluble polyethylene glycol (PEG) hydroxycamptothecin (HCPT) derivative solid product. g, the yield is 63.18%, and the weight average molecular weight is 30800.

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Abstract

The invention provides a method for preparing water soluble pegylation hydroxycamptothecine derivatives by solid phosgene, which belongs to the technical field of water soluble polymer synthesis and degradable medical application. The method adopts BTC is adopted as a coupling agent, selects methenyl chloride as a solvent and pyridine as a catalyst, uses the characteristic of bifunctionality of hydroxycamptothecine, and introduces water soluble polyethylene glycol into the 10th position and the 20th position of the hydroxycamptothecine through a carbonic ester bond. A yellow solid product can be obtained by precipitating and drying by a mixed solution of absolute methanol and absolute aether. The polymer is connected by ester bonds, can be degraded in body via metabolism, can effectively avoid the problem of kidney accumulation generation, and can prominently improve water solubility, structure stability, and the like of the hydroxycamptothecine.

Description

technical field [0001] The invention belongs to the technical field of water-soluble polymer synthesis and degradable medical polymers, and relates to a preparation method of water-soluble PEGylated hydroxycamptothecin derivatives, in particular to the preparation of water-soluble PEGylated hydroxycamptothecin by using solid phosgene method of base derivatives,. Background technique [0002] Camptothecin (CPT) is an alkaloid extracted from Camptotheca involucrata, a plant unique to China, firstly by American chemist Wall et al. It has strong antitumor activity. The anti-tumor mechanism of camptothecin can be simply described as: the camptothecin in the form of lactone ring acts on the binding site of the DNA-Topo complex to form a stable CPT-DNA-Topo complex, which breaks the DNA . In the S phase of the cell cycle, DNA replication encounters a roadblock formed by the ternary complex, which inhibits DNA synthesis and eventually leads to cell apoptosis in the S cycle. Since...

Claims

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Application Information

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IPC IPC(8): A61K47/48A61K31/4745A61P35/00C08G65/48A61K47/60
Inventor 谭业邦王月霞
Owner SHANDONG UNIV
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