N-(2-hydroxypropyl) methacrylamide polymer based nanoparticles and preparation method thereof

A technology of methacrylamide and polymer, applied in the field of nanoparticles and its preparation through the mucus barrier, N-methacrylamide (HPMA) polymer and its derivatives

Active Publication Date: 2016-03-23
SICHUAN UNIV
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  • N-(2-hydroxypropyl) methacrylamide polymer based nanoparticles and preparation method thereof
  • N-(2-hydroxypropyl) methacrylamide polymer based nanoparticles and preparation method thereof
  • N-(2-hydroxypropyl) methacrylamide polymer based nanoparticles and preparation method thereof

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Embodiment 1

[0057] Synthesis of the HPMA polymer modified by embodiment 1 glycylglycine (negative charge)

[0058] Mix 30mL of freshly steamed methacryloyl chloride with 15mL of dichloromethane, slowly drop into 77mL of dichloromethane solution containing 21mL of 1-amino-2-propanol and 32g of sodium carbonate, and rise to room temperature after the addition is complete. Stir for 1h. Then the reaction solution was placed in a low-temperature cold bath at -50°C for 1 h, and a white precipitate was generated. After filtration, the precipitate was recrystallized with acetone, and the white crystal was HPMA monomer.

[0059] Mix 8.71mL of methacryloyl chloride with 30mL of dichloromethane, slowly drop into the sodium hydroxide solution containing 9.79g of glycylglycine under stirring at -15°C, and at the same time drop into 1M sodium hydroxide solution to adjust the pH to 9- 10. Stir at room temperature for 1.5h. The dichloromethane layer was separated and washed with 20 mL of water, the ...

Embodiment 23

[0061] Example 23 - Synthesis of (aminopropyl) methacrylamide salt (positive charge) modified HPMA polymer

[0062]With 2,2'-azobisisobutyronitrile (AIBN) as the initiator, methanol as the solvent, polymer monomers HPMA, 3-(aminopropyl) methacrylamide salt (APMA) (HPMA:APMA=80 :20mol%) to generate HPMA polymer precursors through radical polymerization solution reaction (polymer monomer: initiator: solvent = 12.5:2:85.5wt%).

[0063] AIBN, HPMA and APMA were weighed into ampoules according to the above proportions, dissolved in an appropriate amount of methanol, sealed with nitrogen gas, and stirred at 50°C for 24 hours. Precipitate and purify in ether, remove the remaining solvent and ether-soluble precipitate, dissolve the product with deionized water, dialyze, and freeze-dry to obtain 3-(aminopropyl)methacrylamide salt-modified HPMA polymer.

Embodiment 3 12

[0064] Synthesis of the HPMA polymer modified by embodiment 3 dodecylamine (hydrophobic)

[0065] Take 8g of the crystallized MA-GG-OH monomer in Example 1 and dissolve it in 80mL of dimethylformamide (DMF), then add 6.11g of p-nitrophenol (ONp for short) and 9.07g of N,N-dicyclohexyl Carbodiamine, stirred at -10°C for 3 hours, raised to room temperature and stirred for 8 hours, and filtered to remove the precipitate. Remove DMF under reduced pressure at 50°C, add ethyl acetate, recover the solvent, wash the obtained solid with ether, recrystallize with a mixture of ethanol:water (2:1), and place it at 4°C to obtain white crystals that are MA-GG-ONp single body.

[0066] With 2,2'-azobisisobutyronitrile (AIBN) as the initiator and acetone as the solvent, the polymer monomers HPMA, MA-GG-ONp (HPMA: MA-GG-ONp=80:20mol%) passed through the free Based on the polymerization precipitation reaction to generate HPMA polymer precursor (polymer monomer: initiator: solvent = 12.5:2:8...

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Abstract

The invention discloses an N-(2-hydroxypropyl) methacrylamide polymer based nanoparticles capable of overcoming a mucus barrier and a preparation method thereof. The nanoparticles consist of nucleuses and shells, wherein the kernels are a nanometer compound prepared from a biocompatible carrier material and active ingredients, and the shells are an HPMA polymer and its derivatives.

Description

technical field [0001] The present invention relates to a kind of N-(2-hydroxypropyl) methacrylamide (HPMA) polymer and its derivatives which can overcome mucus barrier, in particular to a kind of N-(2-hydroxypropyl) methacrylamide Nanoparticles of (HPMA) polymers and derivatives thereof passing through the mucus barrier and a preparation method thereof belong to the field of pharmaceutical preparations. Background technique [0002] Mucus is a complex hydrogel composed of proteins, carbohydrates, lipids, inorganic salts, antibodies, bacteria and cell debris (Adv.Drug.Deliv.Rev.,2012,64:557-570), covered in Human gastrointestinal tract, respiratory tract, eyes and cervix and other mucous membrane surfaces. On the one hand, the mucus layer plays a vital role in human health by adsorbing and rapidly removing pathogens and foreign substances; at the same time, the mucus layer also constitutes an important physiological barrier that must be crossed for mucosal drug delivery. ...

Claims

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Application Information

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IPC IPC(8): A61K47/32A61K9/51
Inventor 黄园刘敏山伟张志荣
Owner SICHUAN UNIV
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