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PH-responsive comb-like copolymer and preparation and application thereof

A comb-like copolymer and responsive technology, applied in the field of drug sustained and controlled release materials, can solve problems such as unsatisfactory performance, and achieve the effects of precise control of molecular weight and polydispersity, drug protection, and structural stability

Inactive Publication Date: 2012-08-15
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Judging from the existing research reports, the polymer micelle drug-loading system currently used in the oral system of poorly soluble drugs is far from satisfactory performance.

Method used

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  • PH-responsive comb-like copolymer and preparation and application thereof
  • PH-responsive comb-like copolymer and preparation and application thereof
  • PH-responsive comb-like copolymer and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Synthesis of the bifunctional initiator hydroxyethyl 2-bromoisobutyrate (HEBriB). Into a 150 mL reaction bottle, add a stirrer and seal it. After evacuating and blowing argon for 3 times, under the protection of argon, add ethylene glycol (112 ml, 2 mol), triethylamine (TEA, 11.13 ml, 80 mmol), cooled to 0 °C, and then slowly added 2-bromoisobutyryl bromide (0.989 ml, 80 mmol) dropwise, then reacted at 0 °C for 2 h, then raised the temperature to 40 °C for 5 h. After the reaction was completed, cool at room temperature, add 100 ml of deionized water, then extract 3 times with chloroform, combine the organic phases, and use dilute HCl, saturated NaHCO 3 The solution was washed with water and dried over anhydrous magnesium sulfate. Low boiling point substances were removed by rotary evaporation, and then HEBriB was distilled off under reduced pressure.

Embodiment 2

[0077] (1) Synthesis of macromolecular initiator HO-P t BMA-Br (target molecular weight 5000). Weigh a certain amount of CuBr 2 (11.2 mg, 0.05 mmol) was placed in a 50 mL dry eggplant-shaped bottle with a stirring bar, sealed with a reverse rubber stopper, and vacuum-filled with argon three times. Under the protection of argon, the solvent toluene (20 ml), the monomer t Add BMA (5.715 mL, 35.2 mmol) and ligand PMDETA (0.210 mL, 1 mmol) into the bottle, stir for 15 min to form the catalyst complex, add the reducing agent Sn(Oct) 2(0.162 mL, 0.5 mmol) and then stirred for 5 min. After three freezing-pumping-heating cycles with liquid nitrogen, argon was introduced, and the initiator HEBriB (0.165 mL, 1 mmol) was added dropwise with a syringe, and then transferred to an oil bath at 90 °C for 2 h. After the reaction is complete, cool to room temperature, add 50 mLTHF, stir to dissolve, and then use a neutral alumina column to remove the catalyst CuBr 2 (THF as eluent). The o...

Embodiment 3

[0083] (1) Synthesis of macromolecular initiator HO-P t BMA-Br (target molecular weight 8400). Weigh a certain amount of CuBr 2 (11.2 mg, 0.05 mmol) was placed in a 50 mL dry eggplant-shaped bottle with a stirring bar, sealed with a reverse rubber stopper, and vacuum-filled with argon three times. Under the protection of argon, the solvent toluene (20 ml), the monomer t Add BMA (6.751 mL, 59 mmol) and ligand bpy (0.134 mL, 1 mmol) into the bottle, stir for 15 min to form the catalyst complex, add the reducing agent Sn(Oct) 2 (0.224 mL, 0.7 mmol) and then stirred for 5 min. After three freezing-pumping-heating cycles with liquid nitrogen, argon was introduced, and the initiator HEBriB (0.214 mL, 1.33 mmol) was added dropwise with a syringe, and then transferred to an oil bath at 60 °C for 4 h. After the reaction is complete, cool to room temperature, add 50 mLTHF, stir to dissolve, and then use a neutral alumina column to remove the catalyst CuBr 2 (THF as eluent). The ob...

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Abstract

The invention discloses pH-responsive comb-like copolymer and preparation and application thereof. The preparation includes obtaining pH-responsive group by ARGETATRP (activator regeneration by electron transfer and atomic transfer radical polymerization), obtaining hydrophobic group by ROP (ring opening polymerization), using the pH-responsive group and the hydrophobic group to form block copolymer, using the block copolymer as macroinitiator to initiate ARGETATRP of hydrophobic macromers, and obtaining the pH-responsive amphipathic comb-like copolymer by selective hydrolysis reaction. The proportion of functional groups in the polymer molecule is easy to regulate. The synthetic process is simple, and yield is high. The hydrophobic group and the pH-responsive group obtained by dialysis form polymeric micelles of a shell, drug slightly soluble in water can be entrapped in a core of the polymeric micelles, the drug is kept to release slowly in the presence of gastric juice, and the drug is quickly and controllably released in intestines.

Description

technical field [0001] The invention relates to the technical field of drug sustained and controlled release materials, in particular to a pH-responsive comb copolymer and its preparation method and application. Background technique [0002] Oral preparations are a routine treatment that is more acceptable to patients. However, when taken orally, many drugs are released or even degraded in the stomach and cannot effectively reach the treatment site, resulting in low bioavailability. The advantage of polymer micelles as a drug delivery system is that it has a unique hydrophobic core, which can enhance the drug loading capacity, provide a suitable microenvironment for hydrophobic drugs, and serve as a tool to directly deliver drugs to specific tissues or organs . Meanwhile, the hydrophilic block can provide a stable interface between the hydrophobic core and the solvent environment. In addition, suitable particle size (20-200nm) and low CMC value are also very important, th...

Claims

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Application Information

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IPC IPC(8): C08F293/00C08F8/12C08G63/06C08G65/48A61K47/32A61K9/19
Inventor 章莉娟林文静杨友强杨楚芬
Owner SOUTH CHINA UNIV OF TECH
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