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Conjugate conjugated from polyethylene glycol and curcumin derivative

A technology of curcumin derivatives and polyethylene glycol is applied in directions such as pharmaceutical combinations, medical preparations of non-active ingredients, active ingredients of ketones, etc., and can solve the problems of high cost, many preparation process steps, complex formula and the like

Inactive Publication Date: 2009-09-09
ZHEJIANG CHINESE MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these solutions still have defects such as complicated formula, many preparation process steps, and high cost.

Method used

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  • Conjugate conjugated from polyethylene glycol and curcumin derivative
  • Conjugate conjugated from polyethylene glycol and curcumin derivative
  • Conjugate conjugated from polyethylene glycol and curcumin derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: monomethoxy polyethylene glycol 2k -OCO-glycine-curcumin (mPEG 2K -OCO-Gly-Cur) synthesis

[0047] 1. mPEG 2K -Synthesis of pNC: Weigh mPEG 2K (purchased from Fluka Company) 20.0g (10.0mmol), add 100ml toluene to dissolve, evaporate under reduced pressure at 60°C; add 200ml temporarily dried CH 2 Cl 2 Dissolve, then weigh 6.465g (30.0mmol) of pNPC and add it to the above system, stir and add 6ml of temporary dry Py, stir and react at room temperature (about 20°C) in the dark for about 12h; Crystallization for 2 hours; suction filtration, rinsing with anhydrous ether, recrystallization once with anhydrous ether, vacuum-dried white product 20.85g, yield 96.32%.

[0048] Accurately weigh an appropriate amount of the above product, dissolve it with 0.1M NaOH, and measure the absorbance value at 402nm, according to the molar absorptivity of 18400cm -1 m -1 The amount of p-nitrophenol released was calculated, and the purity of the product was es...

Embodiment 2

[0054] Embodiment 2: monomethoxy polyethylene glycol 5k -OCO-glycine-curcumin (mPEG 5K -OCO-Gly-Cur) synthesis

[0055] Its preparation method is basically the same as Example 1, and the main differences of each step are:

[0056] 1. mPEG 5K -Synthesis of pNC: Weigh mPEG 5K (purchased from Fluka Company) 40.0g (8.0mmol), add about 200ml of toluene to dissolve, evaporate under reduced pressure at 60°C; add 300ml of temporarily dried CH 2 Cl 2 Dissolved, then weighed 7.257g (36.0mmol) of pNPC and added to the above system, stirred and added 6ml of temporary dry Py, and stirred at room temperature in the dark for 12h; the product was 39.86g, the yield was 96.47%, and the purity was greater than 95.64%.

[0057] 2. mPEG 5K -OCO-Gly synthesis: Weigh glycine (hereinafter referred to as Gly) 2.402g (32.0mmol), dissolve with 150ml distilled water, add 100ml acetonitrile (H 2 O / CH 3 CN=3 / 2) and 20.66g (4.0mmol) mPEG 5k -pNC, the pH value of the system was adjusted to...

Embodiment 3

[0060] Embodiment 3: polyethylene glycol 6k -(OCO-Glycine-Curcumin) 2 [PEG 6K -(OCO-Gly-Cur) 2 ]Synthesis

[0061] The preparation method is basically the same as Example 1, and the main differences of each step are:

[0062] 1. PEG 6K -(pNC) 2 Synthesis: weigh PEG 6K (purchased from Fluka Company) 20.0g (3.33mmol), add 150ml toluene to dissolve, evaporate under reduced pressure at 60°C; add 350ml temporarily dried CH 2 Cl 2 Dissolve, then weigh 4.031g (20.00mmol) of pNPC and add it to the above system, stir and add 6ml of temporary dry Py, and stir at room temperature in the dark for about 12h; the product is 19.99g, the yield is 94.84%, and the purity is greater than 93.12%.

[0063] 2. PEG 6K -(OCO-Gly) 2 Synthesis: take glycine 2.40g (32.0mmol), dissolve with 150ml distilled water, add 100ml acetonitrile (H 2 O / CH 3 CN=3 / 2) and 12.66g (2.0mmol) PEG 6k -(pNC) 2 , the pH value of the system was adjusted at 8.5 with triethylamine, and the react...

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Abstract

The invention belongs to the field of medicinal chemistry, and more particularly relates to conjugate conjugated from polyethylene glycol and curcumin derivative as shown in formula 1 and pharmaceutically acceptable salt thereof, wherein R1 and R2 are independently selected from nitro, amidogen, bi-low alkyl amidogen and low alkoxy; R3 and R4 are independently selected from halogen, nitro and hydrogen; R5 is low alkyl or hydrogen; R6 is hydrogen or low alkyl that can be substituted by low alkyl, nitro, hydroxide radical or sulfhydryl which are randomly selected; and n is 1 or 2. The conjugate has good water solubility, overcomes the disadvantages of poor water solubility, low bioavailability, and the like, existing in curcumin, and has low preparation cost and better antitumor activity. In addition, the invention also relates to the pharmaceutical composition, the preparation method and the application as medicament of the conjugate.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular, the invention relates to a conjugate of a biodegradable curcumin derivative and polyethylene glycol. In addition, the present application also relates to the pharmaceutical composition, preparation method and application as a medicine based on the conjugate. Background technique [0002] Curcumin (Curcumin, hereinafter referred to as Cur) is a polyphenol derivative, which is the main active ingredient in the root of ginger plant turmeric. It has anti-inflammatory, anti-oxidation, anti-mutagenic, anti-aging, anti-HIV Blood lipids, anti-atherosclerosis, drug sensitization and anti-tumor and other pharmacological activities; it has certain preventive and therapeutic effects on cardiovascular diseases, neuropathy and cancer. The National Cancer Institute of the United States has listed it as a third-generation anti-cancer drug, and it was listed in the United States Pharmacopoeia in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/48A61K31/12A61P35/00A61K47/60
Inventor 丁志山蒋福升高承贤陈铌铍金波吕圭源
Owner ZHEJIANG CHINESE MEDICAL UNIVERSITY
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