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PEG-modified triacontanol water-soluble prodrug

A triacontanol, water-soluble technology, applied in the field of water-soluble triacontanol macromolecular prodrugs, can solve the problem of poor water solubility of triacontanol and low attention.

Active Publication Date: 2018-05-08
陈西敬
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Triacontanol has a wide range of functions, but currently there is not much attention to the poor water solubility of triacontanol, and there is almost no related research on structural modification of triacontanol

Method used

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  • PEG-modified triacontanol water-soluble prodrug
  • PEG-modified triacontanol water-soluble prodrug
  • PEG-modified triacontanol water-soluble prodrug

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0087] Example 1 Preparation of PEG-modified triacontanol linked by amide-ester linkage

[0088] (1) Preparation of compound a

[0089] Prepare 10mmol mPEG 2k Dissolved in toluene and dried by azeotropic distillation to remove the toluene, the solution was first warmed and then cooled in an ice-water bath (under nitrogen atmosphere). A mixture of pyridine (20 mmol) and methanesulfonyl chloride (80 mmol) was added and reacted overnight under nitrogen. The solution was filtered under vacuum until clear, precipitated with ether, filtered, and dried in vacuo. The resulting product was mixed with potassium phthalimide, added with 100 mL of DMF, placed in nitrogen, and stirred at 120°C for 4 hours. The precipitate was filtered off and dissolved in 200 mL of ethanol, then 10 mL of hydrazine hydrate was added. The mixture was heated to reflux for 4 hours. After cooling to room temperature, the product was precipitated by adding diethyl ether dropwise to the solution. The precipi...

example 2

[0093] Add compound b (0.5g), triacontanol (0.5g), EDCI (1mol), DIPEA (3mol), DMAP (0.05g), 20ml of dichloromethane into a 100ml one-necked bottle, and stir overnight at room temperature. The next day, add 50ml of dichloromethane to the reaction flask, wash twice, dry the organic phase with anhydrous sodium sulfate, and perform column chromatography (developing solvent is dichloromethane:methanol 15:1), to obtain compound c (see figure 1 )0.51g, yield 82.6%. Example 2 Preparation of PEG-modified triacontanol with succinate as the linkage

[0094] (1) Preparation of compound d

[0095] mPEG 2k5 mmol was dissolved in toluene and dried by azeotropic distillation, then 25 mmol of succinic anhydride, DMAP (10 mmol) and triethylamine (10 mmol) were added, and the mixture was stirred overnight at room temperature. After the reaction was complete, the mixture was cooled and placed in CH 2 Cl 2 , and precipitate the polymer with ether. The precipitate was filtered, washed, and dr...

example 3

[0098] Example 3 Preparation of PEG-modified Triacontanol Linked to Glycine

[0099] (1) Preparation of compound f

[0100] Compound d 5mmol, DCC 10mmol and hydroxysuccinimide 10mmol, DMAP 5mmol were added into dichloromethane, and then the reaction mixture was stirred at room temperature for 24h. Dichloromethane was added to the mixture for multiple extractions, and the organic phases were combined, concentrated, and ether was added for precipitation. The precipitate was filtered, washed, dried by adding anhydrous sodium sulfate, and the residue was recrystallized with anhydrous ether to obtain active ester compound f.

[0101] (2) Preparation of compound g

[0102] Dissolve 5mmol of compound f in DMF, after the compound is completely dissolved, add 10mmol of glycine NaHCO 3 solution, then the reaction mixture was stirred overnight at room temperature, filtered and evaporated under reduced pressure, dichloromethane and water were added to the concentrate, the pH was adjust...

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Abstract

The invention relates to a preparation method and anticancer therapeutic effects of a triacontanol water-soluble macromolecular prodrug based on polyethyleneglycol. According to the prodrug, triacontanol is taken as a model drug, and the water-soluble prodrug of the triacontanol is prepared by chemically bonding PEG with the triacontanol through covalent bonds by means of easily degradable ester bonds. The PEG-triacontanol prodrug can effectively improve water-solubility, tumor targeting and stability of the triacontanol and prolong half-life in vivo of the triacontanol, is convenient to use,and meanwhile has good anti-cancer effects. The preparation method of the triacontanol water-soluble macromolecular prodrug has the advantages that the preparation method is simple and convenient andapplicable to large-scale production, so that application range of the triacontanol is wider.

Description

technical field [0001] The invention relates to a polyethylene glycol-based water-soluble triacontanol macromolecular prodrug and a preparation method and application thereof. Background technique [0002] Triacontanol is a long-chain fatty alcohol composed of 30 carbon atoms, also known as meliflon alcohol, which is a natural, non-toxic and highly effective plant growth regulator. Triacontanol is ubiquitous in the waxes of most animals and plants, and is often combined with higher fatty acids to form esters in various waxes. So far, triacontanol has been widely used in crop production increase, flower cultivation, edible fungus cultivation, and achieved good results. Triacontanol can increase the yield by increasing the activity of various enzymes, promoting nitrogen metabolism, increasing the content of chlorophyll in leaves, and promoting photosynthesis. Triacontanol is also a component of the new lipid-lowering drug prilacol, which can lower serum cholesterol levels. ...

Claims

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Application Information

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IPC IPC(8): A61K47/60A61K31/045A61P35/00A61P3/06C08G65/334C08G65/333
CPCA61K31/045C08G65/33396C08G65/3346C08G2650/04C08G2650/38C08G2650/50
Inventor 陈西敬李宁鲁晓雨方敏
Owner 陈西敬
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