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PH response/membrane adhesive amphiphilic block copolymer as well as preparation method and application thereof

A technology of amphiphilic block and copolymer, which can be used in pharmaceutical formulations, medical preparations of non-active ingredients, emulsion delivery, etc. It can solve problems such as complex preparation process, negative charge, and functional limitations of membrane adhesion. , to prolong the residence time and promote the effect of drug absorption

Active Publication Date: 2017-01-04
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

PiyasiMukhopadhyay et al. mixed chitosan with membrane adhesion and pH-sensitive alginate and insulin to prepare nanoparticles with core-shell structure, which separated pH sensitivity and membrane adhesion, and the preparation process was complicated. Particles are still negatively charged, membrane adhesion function is limited [Mukhopadhyay P, Chakraborty S, Bhattacharya S, pH-sensitive chitosan / alginate core-shell nanoparticles for efficient and safe oral insulin delivery, Int J BiolMacromol, 2015, 72: 640- 648]

Method used

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  • PH response/membrane adhesive amphiphilic block copolymer as well as preparation method and application thereof
  • PH response/membrane adhesive amphiphilic block copolymer as well as preparation method and application thereof
  • PH response/membrane adhesive amphiphilic block copolymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] (1) Synthesis of membrane-adhesive monomer tert-butoxycarbonyl (Boc)-protected aminoethyl methacrylate (Boc-AEMA)

[0084] Take a 100ml dry round-bottomed flask and place it in an ice-salt bath, add 10mL of absolute ethanolamine and 40mL of dichloromethane, stir magnetically for 15min, dissolve 30g of di-tert-butyl dicarbonate (O) in 50ml of dichloromethane and slowly add it dropwise to Burn in the round bottom bottle, continue to stir in the ice-salt bath for 20 minutes after the dropwise addition, and then transfer to room temperature to react for 12 hours. After the reaction, wash the reaction solution with 10% solution for 3 times, and then wash with deionized water for 3 times , take the organic phase and dry it with an appropriate amount of anhydrous for 2 hours. After drying, filter under reduced pressure and rotary evaporation to obtain a colorless transparent viscous liquid, and dry it in vacuum at 40°C for 24 hours to obtain Boc-protected ethanolamine.

[0085...

Embodiment 2

[0093] (1) The synthesis of the membrane-adhesive monomer tert-butoxycarbonyl (Boc)-protected aminoethyl methacrylate (Boc-AEMA) is the same as the step (1) in Example 1.

[0094] (2) Synthesis of macromolecular initiator P(MMA-co-tBMA)-Br (A:B=30:45)

[0095] Take a 50ml dry eggplant-shaped bottle, weigh (9mg, 0.04mmol) and put it in it, seal it with a rubber stopper, evacuate and blow argon for 3 times, and inject toluene (12mL), MMA and (3.180mL, 30mmol), tBMA (7.35mL, 45mmol) and the ligand PMDETA (0.130mL) were added to the bottle, stirred magnetically for 30min to form a catalyst complex, and the reducing agent (0.195mL, 0.6mmol) was dissolved in 3ml of toluene and injected into In the reaction flask, the stirring was continued for 30 min, and the freezing-pumping-ventilating-heating cycle was performed 3 times with liquid nitrogen, the initiator EBriB (0.147ml) was injected, and the reaction was carried out in a 75°C oil bath for 2h. After the reaction is complete, coo...

Embodiment 3

[0101] Determination of critical micelle concentration of a pH-responsive / membrane-adhesive amphiphilic block copolymer by pyrene fluorescent probe method.

[0102] (1) Prepare a certain concentration of pyrene solution: accurately weigh 2.43mg of pyrene and dissolve it in 10ml of acetone, pipette it into a 100ml volumetric flask, and dilute it with acetone to make a concentration of 12×10 -5 The pyrene solution of M is ready for use. Take 5ml 12×10 -5 The pyrene solution of M was diluted with acetone to 6×10 -5 M.

[0103] (2) Preparation of sample solution: Weigh 10mg of amphiphilic block copolymer (product of Example 1) P(MMA-co-MAA)-b-P(AEMA) and dissolve it in 3ml of acetone, and accurately add 10ml of deionized under stirring water, stirred overnight to completely volatilize the acetone to obtain a 1mg / ml polymer mother liquor, dilute the polymer mother liquor into a series of 0.0001~1mg / ml solutions, take 10 10ml clean volumetric flasks, add 0.1ml 6×10 -5 M pyrene s...

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PUM

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Abstract

The invention discloses a pH response / membrane adhesive amphiphilic block copolymer as well as a preparation method and application thereof. According to the preparation method, methacrylic acid with an isoelectric point of 5.0-6.5 is utilized as a pH response monomer, methacrylic aminoethyl ester with pH-insensitive hydrophilia is utilized as a membrane-adhesive monomer, an electron transfer activator regeneration-atom transfer free radical active polymerization method is adopted, a pH response monomer and hydrophobic monomer block copolymer is firstly prepared; and by taking the pH response monomer and hydrophobic monomer block copolymer as a macroinitiator, the membrane-adhesive monomer, namely the methacrylic aminoethyl ester is polymerized, and finally acidolysis reaction is performed, so that the pH response / membrane adhesive amphiphilic block copolymer is prepared. The pH response / membrane adhesive amphiphilic block copolymer is capable of being self-assembled to form a core-shell structure micelle in an aqueous solution, has favorable pH sensibility and membrane adhesion property, lower critical micelle concentration and relaively small micelle particle size, and can be used in drug delivery systems for oral medication application of polypeptide or proteinic drugs.

Description

technical field [0001] The invention relates to the field of biomedical functional polymer materials, in particular to an amphiphilic block copolymer with pH sensitivity and film adhesion and a preparation method thereof. Background technique [0002] Oral administration has many advantages such as convenient use, relatively cheap cost, and good patient compliance, and is a routine treatment method that is more easily accepted by patients. However, the oral administration process is limited by many factors, resulting in low bioavailability of drugs in the gastrointestinal tract, especially most polypeptide and protein drugs (such as insulin), due to the large molecular weight and poor fat solubility of these drugs, Biomembrane permeability is low, and there are a large number of peptidases and proteolytic enzymes in the gastrointestinal tract. Drugs are prone to first-pass effect and are decomposed and digested after oral administration. Therefore, the oral therapeutic appli...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F293/00C08F220/18C08F220/14C08F220/34C08F8/00C08J3/00A61K9/107A61K47/32A61K47/18
CPCA61K47/32C08F8/00C08F220/18C08F220/1804C08F293/00C08J3/00C08J2353/00C08F220/14
Inventor 吴志民胡文尧刘跃进谢坚韧
Owner XIANGTAN UNIV
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