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Dendritic grafted polycaprolactone

A technology of polycaprolactone and caprolactone, which is applied in the field of organic synthesis and biomedical materials, can solve the problems of unsatisfactory drug-loading capacity, poor affinity, and micelles that need to be improved, and achieve good application value and large drug-loading capacity , good micellar stability

Inactive Publication Date: 2011-12-14
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, common linear aliphatic polyesters such as polycaprolactone and polylactic acid are usually polymers with high crystallinity, which makes them have poor affinity with drugs and their drug loading capacity is not ideal
In addition, the stability of micelles composed of amphiphilic polymers also needs to be improved

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The preparation of 4-(benzyloxyethyl) cyclohexanol: 22.32g (0.1921mol) of 4-hexanediol and 0.93g (0.0400mol) of chopped metal sodium were put in a round bottom flask, Under the protection of argon, heat to 120°C and stir with a magnet to disperse the sodium as much as possible. After 10 hours, it becomes a dark brown viscous liquid, and after being kept at 135°C for 12 hours, a dark brown lump is obtained. Cool to 50°C, inject about 70 mL of dry DMF to dissolve the brown lump. Keeping the temperature at 70°C, 12.29 g (0.0400 mol) of monobenzylethylene glycol p-toluenesulfonate dissolved in 16 mL of DMF was added dropwise with a syringe, and a total of about 92 mL of DMF was added. Stir and react at 70°C for 22h. After cooling to room temperature, filter under reduced pressure. The DMF in the filtrate was distilled off under reduced pressure and cooled to room temperature. Add about 60 mL of dichloromethane to precipitate excess cyclohexanediol, and filter under redu...

Embodiment 2

[0028] Preparation of 4-(benzyloxyethyl)cyclohexanone: In a 150mL flask, add 3.58g 4-(benzyloxyethoxy)cyclohexanol (0.0143mol) and 90mL CH 2 Cl 2 5.5 mL of Jones reagent was added dropwise while stirring, and the reaction was stirred at room temperature for 10 minutes after the addition was completed. After filtration, the filtrate was concentrated and purified by silica gel column chromatography to obtain 1.86 g of a colorless liquid with a yield of 52%. 1 H NMR (CDCl 3 , 300MHz, TMS): δ7.35-7.26(m, 5H), 4.59(s, 2H), 3.77-3.75(m, 1H), 3.71-3.65(m, 4H), 2.62-2.57(m, 2H) , 2.27-2.23(m, 2H), 2.12-2.08(m, 2H), 1.97-1.90(m, 2H). 13 C NMR (CDCl 3 , 75MHz,): δ211.7, 138.4, 128.6, 127.9, 73.5, 73.4, 69.9, 68.1, 37.4, 30.7.Anal.: Cald.for C 15 h 20 o 3 : C72.55, H 8.12; Found: C 72.14, H 8.36.

Embodiment 3

[0030] Preparation of 4-benzyloxyethoxy-ε-caprolactone (BECL): Add 2.09g of 70% mCPBA (8.47mmol) and magnetons in a 150mL round bottom flask, add 20mL CHCl 3 , and stirred until the mCPBA was completely dissolved. Add dropwise with 5mL CHCl 3 1.86 g (7.47 mmol) of dissolved 4-(benzyloxyethoxy) cyclohexanone was stirred for 5 hours. The solution in which a large amount of white crystals were precipitated was suction filtered, and the filtrate was collected and washed with 120mL saturated NaHCO 3 The filtrate was washed 3 times with distilled water, and the residue was concentrated and purified by silica gel column chromatography to obtain 1.66 g of a colorless liquid with a yield of 84%. 1 H NMR (CDCl 3 , 300MHz, TMS): δ7.38-7.27(m, 5H), 4.56(s, 2H), 4.50(dd, J 1 =10Hz,J 2 =13Hz, 1H), 4.04(dd, J 1 =6Hz,J 2 =13Hz, 1H), 3.72(br s, 1H), 3.63(s, 4H), 2.99(t, J=13Hz, 1H), 2.40(dd, J 1 =8.4Hz,J 2 =14.4Hz, 1H), 2.15-1.77(m, 4H). 13 C NMR (CDCl 3, 75MHz,): δ176.3, 138.4, 128...

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Abstract

The invention discloses an arborescent graft polycaprolactone, and also discloses an arborescent graft polycaprolactone-polyethylene glycol copolymer and application of the copolymer as a drug carrier. In the invention, a novel arborescent graft polycaprolactone-polyethylene glycol copolymer is prepared by preparing a new epsilon-caprolactone derivative (4-benzyloxy-ethoxy-epsilon-caprolactone; BECL) from 1,4-cyclohexanediol used as a raw material, then carrying out ring-opening copolymerization on the BECL and epsilon-caprolactone in the presence of stannous iso-caprylate used as a catalyst, carrying out palladium-carbon catalytic hydrogenation to remove benzyl protecting groups to obtain the arborescent graft polycaprolactone with multiple hydroxyl groups, and finally grafting and introducing hydrophilic polyethylene glycol chain segments to the hydroxyl groups with phosgene as a chain extender. In an aqueous medium, the hydrophobic arborescent graft polycaprolactone shrinks to forma core, and the hydrophilic polyethylene glycol chain segments stretch at the periphery, thus forming a unimolecular micelle. As a drug carrier, the micelle has the advantages of large drug carrying capacity and good stability.

Description

technical field [0001] The invention relates to a dendritic grafted polycaprolactone, and also relates to the dendritic polycaprolactone-polyethylene glycol copolymer and the application of the copolymer as a drug carrier, belonging to the fields of organic synthesis and biomedical materials. Background technique [0002] With the broad application prospects of biodegradable polymer materials in the diagnosis and treatment of biological system diseases and the repair or replacement of biological tissues and organs, their research has attracted more and more attention. Biodegradable aliphatic polyester is an important member of biomedical polymer materials. [0003] In order to improve the utilization efficiency of drugs, reduce toxic and side effects, and improve curative effect, the micro-nano and intelligent drug delivery system is the current development trend. Among them, polymer micelles composed of biodegradable amphiphilic polymers are a promising drug delivery syste...

Claims

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Application Information

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IPC IPC(8): C08G63/91C08G63/08C08G81/00A61K47/34
Inventor 钟振林杨正茂凌秀君程娟卓仁禧
Owner WUHAN UNIV
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