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Hydrophobic functional micromolecule-hydrophilic polyamino acid based biodegradable polymer and preparation method and application thereof

A technology for degrading polymers and functional small molecules is applied in the field of amphiphilic biodegradable materials and their preparation, and can solve the problems of difficult surface functionalization and low stability of nano-microspheres.

Active Publication Date: 2016-08-17
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, nanospheres such as PLGA emulsified with TPGS are usually less stable, and the surface is difficult to functionalize

Method used

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  • Hydrophobic functional micromolecule-hydrophilic polyamino acid based biodegradable polymer and preparation method and application thereof
  • Hydrophobic functional micromolecule-hydrophilic polyamino acid based biodegradable polymer and preparation method and application thereof
  • Hydrophobic functional micromolecule-hydrophilic polyamino acid based biodegradable polymer and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment one initiator vitamin E amino (VE-NH 2 )Synthesis

[0068] (1) Preparation of intermediate VE-4-NC: Under nitrogen atmosphere, dichloromethane (30 mL) solution of p-nitrophenyl chloroformate (4-NC, 1.98 g, 9.8 mmol) was heated at 0°C It was added dropwise to a solution of vitamin E (VE, 2.12 g, 4.9 mmol) and pyridine (1.98 mL, 24.5 mmol) in dichloromethane (10 mL) at a rate of 5 seconds. After the dropwise addition was completed, it was transferred to a 30° C. oil bath to react for 24 hours. After the reaction, the by-product pyridinium salt was removed by filtration, and the filtrate was spin-dried by a rotary evaporator to obtain a light yellow viscous crude product of VE-4-NC. Then dissolve the crude product with petroleum ether (b.p: 60-90 ℃), centrifuge to remove impurities, rotary evaporate, and finally vacuum-dry to obtain the yellow viscous oily product VE-4-NC, with a yield of 93.4%;

[0069] (2) Initiator vitamin E amino (VE-NH 2 ) preparation: ...

Embodiment 2

[0071] Embodiment two initiator cholesteryl amino (Chol-NH 2 )Synthesis

[0072] (1) Preparation of intermediate Chol-4-NC: Under nitrogen protection, a solution of p-nitrophenyl chloroformate (4-NC, 1.61 g, 8.0 mmol) in dichloromethane (about 30 mL) was Add slowly dropwise (about 5 seconds per drop) to cholesterol (Chol, 1.55 g, 4.0 mmol) and pyridine (1.56 mL, 20.0 mmol) in dichloromethane (10 mL) under bath conditions. Then, it was reacted in an oil bath at 30°C for one day, the pyridinium salt was removed by filtration, and the crude product was obtained as a white solid by rotary evaporation. Finally, the crude product was purified by washing with ice acetone to obtain the Chol-4-NC product. Yield: 50.4%;

[0073] (2) Initiator cholesteryl amino (Chol-NH 2 ) preparation: Chol-4-NC (1.05 g, 1.9 mmol) was dissolved in dichloromethane (30 mL), and then slowly added dropwise to a twenty-fold excess of ethylenediamine ( 2.57 mL, 38.0 mmol) in dichloromethane (7 mL), react...

Embodiment 3

[0075] Example 3 Vitamin E-poly(γ-diethylene glycol monomethyl ether-L-glutamic acid) (VE-poly(EG 2 -Glu)) synthesis

[0076] Taking n as 5 as an example: the initiator vitamin E amino VE-NH 2 (1.16 g, 2.25 mmol) was dissolved in 37 mL of dichloromethane solvent and placed in a closed reactor. Under nitrogen atmosphere, γ-diethylene glycol monomethyl ether-L-glutamic acid-N-carboxy internal acid anhydride (EG 2 -Glu-NCA) (3.71 g, 13.50 mmol) in dichloromethane (37 mL) was quickly added to the initiator and reacted at 25 °C for 12 hours. The reaction process was monitored by Fourier transform infrared spectroscopy. After the reaction, the reaction solution was concentrated by rotary evaporation to about 18 ml, precipitated with glacial ether, and centrifuged at low temperature (-5°C, 5000 rpm) to collect the precipitate. Finally, it was washed three times with glacial ether and dried in vacuum for 48 hours to obtain a pale yellow product with a yield of 55.8%.

[0077] VE-...

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Abstract

The invention discloses a hydrophobic functional micromolecule-hydrophilic polyamino acid based biodegradable polymer and a preparation method and application thereof. The preparation method includes: preparing a hydrophobic functional initiator at first, initiating an NCA monomer to realize ring-opening polymerization to obtain an amphiphilic surfactant based on functional molecules and polypeptide, and then utilizing the amphiphilic surfactant to emulsification of poly(lactic-co-glycolic acid) (PLGA), polylactic acid (PLA) and poly-Epsilon-caprolactone(PLC) materials to obtain polymer nanoparticles. Further, the emulsifier can also be used as a component constructed on surfaces of nanoparticles, the active terminal amino can be subjected to chemical bonding with targeting molecule with carboxyl to further improve stability of the nanoparticles, and meanwhile, the targeting molecule is introduced. The obtained drug-loaded targeting nanoparticles are of high stability and can be enriched to tumor location well, have good treatment efficacy to various solid tumors including human breast cancer and have low toxic and side effect.

Description

technical field [0001] The invention relates to an amphiphilic polymer, in particular to an amphiphilic biodegradable material constructed from hydrophobic functional small molecules and hydrophilic polyamino acids, as well as its preparation method and application. Background technique [0002] Poly(lactic-glycolic acid) (PLGA) is an FDA-approved biodegradable polymer, which is widely used in biomedical fields such as surgical sutures, tissue engineering scaffolds, and drug-controlled release carriers. PLGA-based biodegradable nanoparticles and microparticles have become one of the most important carriers for drug-targeted long-acting therapy. For example, a variety of PLGA microspheres loaded with protein drugs and peptide drugs such as Depot ® , Decapeptyl ® , Somatulline ® , Nutropin ® , Depot ® , has been clinically used in the treatment of prostate cancer, acromegaly, growth hormone deficiency. PLGA nanoparticles and microparticles are usually prepared by emulsif...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/10A61K47/34A61K9/51C07K5/093C07K5/113C07K7/06C07K7/08
CPCA61K9/5146A61K47/34C07K5/0819C07K5/1021C07K7/06C07K7/08C08G69/10
Inventor 邓超武金田孟凤华钟志远
Owner SUZHOU UNIV
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