Amphipathic tri-block copolymer having pH responsiveness and preparation method of same

An amphiphilic and responsive technology, applied in the direction of non-active ingredient medical preparations, pharmaceutical formulations, emulsion delivery, etc., can solve the problems that hinder the development and application of oral drugs, are easily degraded by acids and enzymes, and have low bioavailability and other problems, to achieve the effect of less catalyst consumption, good stability and simple operation

Inactive Publication Date: 2018-01-19
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Multiple daily injections of medicines are still the way to treat some intractable diseases, such as insulin injections for diabetes, which often cause great inconvenience and pain to patients
However, due to direct oral delivery, many hydrophobic drugs often cannot successfully reach the target site due to problems such as being easily degraded by acids and enzymes in the gastrointestinal tract (GI), and poor membrane permeability, which leads to low bioavailability and hinders The development and application of oral medicine

Method used

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  • Amphipathic tri-block copolymer having pH responsiveness and preparation method of same
  • Amphipathic tri-block copolymer having pH responsiveness and preparation method of same
  • Amphipathic tri-block copolymer having pH responsiveness and preparation method of same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] (1) Synthesis of macroinitiator poly(methyl methacrylate-co-tert-butyl methacrylate)-bromine (P(MMA-co-tBMA)-Br)

[0068] Weigh CuBr 2 (9.0 mg, 0.04mmol) was placed in a 50ml dry eggplant-shaped bottle, sealed with an inversion rubber stopper, and after pumping air-argon for 3 times, the solvent toluene (10 mL), single MMA (3.708 mL, 35 mmol), tBMA (4.765 mL, 30 mmol) and catalyst ligand pentamethyldiethylenetriamine (PMDETA) (0.105 mL, 0.5 mmol) were added to the bottle, stirred for 25 min, and a complex was formed. compound catalyst, the reducing agent Sn(Oct) 2 (0.195 mL, 0.6 mmol) mixed with 3 mL of toluene was injected into the reaction flask, and then stirred for 10 min. After 3 cycles of liquid nitrogen freezing and freezing-pumping-heating and thawing, argon gas was introduced, and the initiator was added dropwise with a syringe. Ethyl 2-bromoisobutyrate (EBriB) (0.147 mL, 1 mmol) was transferred to an oil bath at 80°C for 2 h. After the reaction was completed...

Embodiment 2

[0074] Gel permeation chromatography (GPC, Agilent 1260) to measure the number average molecular weight (Mn) and molecular weight distribution (Mw / Mn) of polymers

[0075] (1) Instrument and operation: guard column (PLgel 5 um), LC quantitative pump, separation column PLgel 5um MIXED-D (serialNo.0006160533-100), separation column PLgel 5um MIXED-D (serial No.0006160533-102), And RI differential refractive index detector. The column was calibrated with monodisperse polystyrene standard sample, the mobile phase (chromatographic grade tetrahydrofuran (THF), flow rate: 1.0mL / min), and the column temperature was 30 o c.

[0076] (2) Preparation of sample solution: Accurately weigh 5mg of sample and dissolve it in 1ml of chromatographic grade tetrahydrofuran (THF) to prepare a sample solution with a concentration of 5m / ml.

[0077] (3) Measurement of Example 1 (poly(methyl methacrylate-co-tert-butyl methacrylate)-bromine (P(MMA-co-tBMA)-Br), poly(methyl methacrylate-co - tert-but...

Embodiment 3

[0079] Determination of Critical Micelle Concentration of pH Responsive Amphiphilic Block Copolymers by Pyrene Fluorescent Probe Method

[0080] (1) Preparation of 3×10-5M (M=mol / l) pyrene solution: Weigh 2.43mg of pyrene and dissolve it in 10ml of acetone solution, pipette it into a 100ml volumetric flask, dilute with acetone solution to make a concentration of 12 ×10 -5 The pyrene solution of M is ready for use, take 5ml 12×10 -5 M pyrene solution, diluted with acetone to 3×10 -5 M.

[0081] (2) Preparation of sample solution: Weigh 10 mg of amphiphilic block copolymer poly(methyl methacrylate-co-tert-butyl methacrylate)-polymethacryloxyethyltrimethylammonium chloride Dissolve P(MMA-co-MAA)-b-PDMC in 3ml of acetone, add 10ml of deionized aqueous solution with pH 6.8 under stirring, and place it at room temperature for 24 hours to completely volatilize the acetone to obtain a 1mg / ml polymer mother solution , and then dilute the polymer mother liquor into a series of 0.000...

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Abstract

The invention discloses an amphipathic tri-block copolymer having pH responsiveness and a preparation method of same, wherein the amphipathic tri-block copolymer is in a linear structure and is composed of functional polymethyl methacrylate (PMMA), polymethylacrylic acid (PMAA) and polymethylacryloxyethyltrimethyl ammonium chloride (PDMC), number-average molecular weight being 4000-13000 g/mol. Ina water solution, the copolymer can be self-assembled to form spherical micelle which has a hydrophobic inner layer and a hydrophilic outer layer. The copolymer has high pH responsiveness, small micelle particle size and low critical micelle concentration, and is suitable for coating a hydrophobic drug as a carrier in the fields of targeted transmission and controllable sustained release.

Description

technical field [0001] The invention relates to the field of functional polymer materials, in particular to a pH-responsive amphiphilic tri-block copolymer and a preparation method thereof. Background technique [0002] Multiple daily injections of medicines are still the way to treat some intractable diseases, such as insulin injections for treating diabetes. This injection method often leads to great inconvenience and pain for patients. However, due to direct oral delivery, many hydrophobic drugs often cannot successfully reach the target site due to problems such as being easily degraded by acids and enzymes in the gastrointestinal tract (GI), and poor membrane permeability, which leads to low bioavailability and hinders The development and application of oral drugs. [0003] Block copolymers refer to monomer groups with two or more different chemical structures and properties in a single linear macromolecule. Macromolecular copolymers with specific chemical structures a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F8/12C08F293/00C08F220/34A61K47/32A61K9/107
Inventor 刘跃进万妮吴志民
Owner XIANGTAN UNIV
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