Separating and purifying method of camptothecin

A technology for separation and purification of camptothecin, applied in the direction of organic chemistry, which can solve the problems of long operation time, high production cost, complicated operation process, etc., and achieve the effect of simple operation, low cost and low energy consumption

Active Publication Date: 2013-08-21
THE NORTHERN RES INST OF NJUST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The commonly used recrystallization method is to obtain the final product after repeated recrystallization of the crude product extracted by solvent or alkali. Although the recrystallization method is easy to operate, the purity is not high; the solvent consumption of the chromatography method is large, and the operation time is long. The loss of finished products in the process is large, resulting in low final yield; although high-speed countercurrent chromatography overcomes the irreversible adsorption consumption, the complex structure of the equipment is not suitable for

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  • Separating and purifying method of camptothecin
  • Separating and purifying method of camptothecin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] In a 100ml three-neck flask equipped with a condensing reflux tube, add 8.75g of a commercially available camptothecin mixture (camptothecin content 80%, about 0.02mol), first use 20ml2mol / L sodium hydroxide solution to open the ring, and the sodium hydroxide The mol ratio with camptothecin is 2:1, then add 5.4g (about 0.03mol) guanidine carbonate respectively, the mol ratio of guanidine carbonate and camptothecin is 1.5:1, and the mixture of 60ml methanol and water (volume ratio is 2:1), at 65°C, stir and heat for 2.5 hours, stop the reaction, let it stand at -10°C for 1h after natural cooling, and precipitate the complex crystals of ring-opening camptothecin and separation reagent, and use 30ml of methanol-water mixed solvent (Volume ratio is 1:3) recrystallization, filtration, add the filter cake to 60ml5mol / L hydrochloric acid, the ring-opened camptothecin will be re-closed to obtain a camptothecin precipitate, and the camptothecin precipitate is obtained by filterin...

Embodiment 2

[0028] In a 100ml three-neck flask equipped with a condensing reflux tube, add 10g of a commercially available camptothecin mixture (camptothecin content 70%, about 0.02mol), first use 20ml2mol / L sodium hydroxide solution to open the ring, and then add 5.4 g (about 0.03mol) of guanidine carbonate, and 30ml of methanol and water mixture volume (volume ratio is 2:1), stirred and heated at 40°C for 3 hours, stopped the reaction, cooled naturally and left at 40°C for 10h, then precipitated and opened the ring The compound crystal of camptothecin and separation reagent is recrystallized with 30ml methanol and water mixed solvent (1:3 volume ratio), filtered, and the filter cake is added to 60ml5mol / L hydrochloric acid, and the ring-opened camptothecin The camptothecin precipitate was obtained by re-closing the ring, and the camptothecin precipitate was filtered, washed with water and dried to obtain 6.4 g of solid, with a yield of 91.4% and a purity of 98.9% by HPLC.

Embodiment 3

[0030] In a 100ml three-neck flask equipped with a condensing reflux tube, add 10.7g of a commercially available camptothecin mixture (camptothecin content 65%, about 0.02mol), first use 20ml2mol / L sodium hydroxide solution to open the ring, and then add 3.8g (about 0.04mol) guanidine hydrochloride, and 70ml of mixed solvent of ethanol and water (volume ratio: 1:1), stirred and heated at 80°C for 2 hours, stopped the reaction, cooled naturally and stood at 15°C for 4h, then precipitated Cyclocamptothecin and separation reagent complex crystals, recrystallized with 30ml methanol and water mixed solvent (volume ratio: 1:2), suction filtration, add the filter cake to 60ml5mol / L hydrochloric acid, the ring-opened camptothecin The ring was closed again to obtain camptothecin precipitate, which was filtered, washed and dried to obtain 6.5 g of solid, with a yield of 92.5% and a purity of 98.0% by HPLC.

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Abstract

The invention relates to a separating and purifying method of camptothecin. The method comprises the following steps of: (1) adding a camptothecin mixture into a sodium hydroxide solution for a ring opening treatment; (2) sequentially adding a separating reagent and a separating solvent to the reaction solution in the step (1) and reacting for 2-3 hours at 40-80 DEG C; naturally cooling; and standing at -10-40 DEG C till compound crystals of the camptothecin with opened rings and the separating reagent for separation; and filtering to obtain a compound crystal crude product of the camptothecin and the separating reagent, wherein the separating reagent is guanidine hydrochloride, guanidine carbonate, guanidine sulfate or guanidine nitrate, and the separating solvent is methanol-water, ethanol-water or acetone-water; and (3) recrystallizing the compound crystal crude product of the open-ring and the separating reagent and filtering, and adding filter cakes into concentrated hydrochloric acid to be uniformly mixed; and then, carrying out suction-filtering, washing and drying to obtain the camptothecin. The method provided by the invention can be used for reasonably and efficiently separating the camptothecin, and provides great convenience for experimental and production works, and meanwhile avoids material and energy source wastes.

Description

technical field [0001] The invention relates to a method for separating and purifying camptothecin, which belongs to the technical field of chemical separation. Background technique [0002] Camptothecin (Camptothecin, CPT) is an alkaloid isolated from Camptotheca acuminata Dence. Camptothecin has significant curative effect on various malignant tumors such as head and neck cancer, gastric cancer, colon cancer, bladder cancer and leukemia. It is the only inhibitor of topoisomerase I found so far. Camptothecins are the second natural medicines with anticancer activity that have been approved for marketing after paclitaxel. [0003] [0004] Camptothecin structure [0005] The currently widely used methods for separating camptotheca alkaloids include recrystallization, chromatography and chromatography, macroporous adsorption resin extraction, polyamide separation and purification, high-speed countercurrent chromatography, supercritical fluid CO2 extraction, etc. The com...

Claims

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Application Information

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IPC IPC(8): C07D491/22
Inventor 李康武金志敏夏春年李亚琴
Owner THE NORTHERN RES INST OF NJUST
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