Polyethylene glycol modified glycyrrhetinic acid and curcumin compound used for resisting hepatic carcinoma, and preparation method thereof

A technology of polyethylene glycol modification and glycyrrhetinic acid, which is applied in the field of medicine, can solve the problems of low purity of reaction products, damage to the health of experimenters, and insufficient liver targeting ability, so as to prolong the circulation time in the body, protect the liver and resist Inflammatory action, little toxicity effect

Inactive Publication Date: 2015-06-17
郑增娟
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, in the prior art, pyridine is generally used as an acid-binding agent to neutralize the hydrochloric acid generated in the reaction, but pyridine is highly toxic, easily damages the health of experimenters, and has high cost, difficult recovery, low reaction yield, and low purity of reaction products. Low water solubility, insufficient liver targeting ability, low efficacy

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] (1) Preparation of polyethylene glycol monomethyl ether-p-toluenesulfonate (mPEG-OTs)

[0054] Accurately weigh 2.0 mmol of polyethylene glycol monomethyl ether mPEG, place it in a dry three-necked flask equipped with a reflux condenser and a mechanical stirrer, add an appropriate amount of dichloromethane, and after the mPEG is completely dissolved, blow nitrogen, and share a small amount of it several times. Add 6.0 mmol of p-toluenesulfonyl chloride TsCl, and then add an appropriate amount of triethylamine TEA, nitrogen protection at room temperature, stirring and reflux reaction for 4h. After the reaction, the reaction mixture was filtered to remove insoluble solids, the filtrate was transferred to a separatory funnel, extracted and washed 3 times with dilute hydrochloric acid, the organic phase obtained was neutralized to pH 7 with saturated sodium carbonate solution, and then washed with distilled water. Dry the organic phase with anhydrous sodium sulfate, let it ...

Embodiment 2

[0062] (1) Preparation of polyethylene glycol monomethyl ether-p-toluenesulfonate (mPEG-OTs)

[0063] Accurately weigh 3.0 mmol of polyethylene glycol monomethyl ether mPEG, place it in a dry three-neck flask equipped with a reflux condenser and a mechanical stirrer, add an appropriate amount of dichloromethane, and after the mPEG is completely dissolved, blow nitrogen, and share a small amount of it several times. Add 9.0 mmol of p-toluenesulfonyl chloride TsCl, and then add an appropriate amount of triethylamine TEA, nitrogen protection at room temperature, stirring and reflux reaction for 6h. After the reaction, the reaction mixture was filtered to remove insoluble solids, the filtrate was transferred to a separatory funnel, extracted and washed 3 times with dilute hydrochloric acid, the organic phase obtained was neutralized to pH 7 with saturated sodium carbonate solution, and then washed with distilled water. Dry the organic phase with anhydrous sodium sulfate, let it st...

Embodiment 3

[0072] (1) Preparation of polyethylene glycol monomethyl ether-p-toluenesulfonate (mPEG-OTs)

[0073] Accurately weigh 4.0 mmol of polyethylene glycol monomethyl ether mPEG, place it in a dry three-neck flask equipped with a reflux condenser and a mechanical stirrer, add an appropriate amount of dichloromethane, and after the mPEG is completely dissolved, blow nitrogen, and share a small amount of it several times. Add 12.0 mmol of p-toluenesulfonyl chloride TsCl, and then add an appropriate amount of triethylamine TEA, nitrogen protection at room temperature, stirring and reflux reaction for 8h. After the reaction, the reaction mixture was filtered to remove insoluble solids, the filtrate was transferred to a separatory funnel, extracted and washed 3 times with dilute hydrochloric acid, the organic phase obtained was neutralized to pH 7 with saturated sodium carbonate solution, and then washed with distilled water. Dry the organic phase with anhydrous sodium sulfate, let it s...

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Abstract

The invention discloses a polyethylene glycol modified glycyrrhetinic acid and curcumin compound used for resisting hepatic carcinoma, and a preparation method thereof. The preparation method comprises the following steps: (1), the preparation of methoxy polyethylene glycol-tosylate (mPEG-OTs); (2), the preparation of methoxy polyethylene glycol-phthalimide (mPEG-PI); (3), the preparation of single-ended amino methoxy polyethylene glycol (mPEG-NH2); (4), the preparation of methoxy polyethylene glycol-glycyrrhetinic acid (mPEG-18beta-GA); (5), the preparation of polyethylene glycol modified glycyrrhetinic acid and curcumin compound (mPEG-GA and CUR compound), wherein the yield of the mPEG-OTs can reach 84.54 percent or above, the yield of the mPEG-PI can reach 88.96 percent or above, the yield of the mPEG-NH2 can reach 88.72 percent or above, and the yield of the mPEG-18beta-GA can reach 82.43 percent or above. The purity of the mPEG-OTs can reach 95.74 percent or above, the purity of the mPEG-PI can reach 96.88 percent or above, the purity of the mPEG-NH2 can reach 99.51 percent or above, the purity of the mPEG-18beta-GA can reach 99.65 percent or above, the yield of the mPEG-GA and the CUR compound can reach 83.31 percent or above, and the purity of the mPEG-GA and the CUR compound can reach 99.78 percent or above.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a polyethylene glycol-modified glycyrrhetinic acid-curcumin complex for anti-liver cancer and a preparation method thereof. technical background [0002] Liver cancer is one of the most common malignant tumors clinically, and its lethality rate is extremely high. According to the latest statistics, about 600,000 new liver cancers are diagnosed every year in the world, ranking fifth among malignant tumors. Serious threat to people's health and life. Clinically, chemotherapy is a commonly used means of cancer treatment, and the combined application of antineoplastic drugs is essential, but drug resistance and serious side effects are easily produced. In order to minimize the physical and mental harm caused by chemotherapy to patients, modern science and technology gradually require the "precise administration" of drugs and their preparations. The liver-targeted drug delivery s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/48A61K31/12A61K31/56A61P35/00A61P1/16A61P29/00
Inventor 郑增娟于英杰张维芬管宇
Owner 郑增娟
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