Preparation method of functional biodegradable nano particle based on polyamino acid

A polyamino acid and nanoparticle technology, which is applied in medical preparations with non-active ingredients, medical preparations containing active ingredients, drug combinations, etc., can solve the problems of low stability of nano-microspheres and difficult surface functionalization

Active Publication Date: 2016-08-24
ZHANGJIAGANG INST OF IND TECH SOOCHOW UNIV +1
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  • 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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  • Preparation method of functional biodegradable nano particle based on polyamino acid
  • Preparation method of functional biodegradable nano particle based on polyamino acid
  • Preparation method of functional biodegradable nano particle based on polyamino acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment one initiator vitamin E amino (VE-NH 2 )Synthesis

[0037] (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%;

[0038] (2) Initiator vitamin E amino (VE-NH 2 ) preparation: ...

Embodiment 2

[0041] Example 2 Vitamin E-poly(γ-diethylene glycol monomethyl ether-L-glutamic acid) (VE-poly(EG 2 -Glu)) synthesis

[0042] 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) monomer 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%.

[0043] VE-poly(EG 2 -Glu) NMR characterizati...

Embodiment 3

[0051] Example Three Using VE-poly(EG x -Glu) n Preparation of PLGA Nanoparticles for Polymeric Surfactants

[0052] Preparation of PLGA nanoparticles (PLGA NPs): with VE-poly(EG 2 -Glu) 5 As a polymer surfactant as an example, 0.9 mL of PLGA in acetone (10 mg / mL) was added dropwise to 9 mL of VE-poly(EG 2 -Glu) 5 In an aqueous solution (0.45 mg / mL), stir at room temperature for 6 h to evaporate acetone, then centrifuge (12000 rpm, 10 min, 4 ℃; SorvallBiofuge Stratos, Thermo Scientific) to collect nanoparticles, and wash once with secondary water to remove free emulsified agent, prepared surface containing VE-poly (EG 2 -Glu) 5 PLGA nanoparticles. The particle size and particle size distribution of nanoparticles can be measured by dynamic light scattering to be 135 nm and 0.06, respectively. The surface of nanoparticles contains VE-poly(EG 2 -Glu) 5 The polyamino acid chain segment can be confirmed by observing the appearance of N peak through X-ray photoelectron spe...

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Abstract

The invention discloses a preparation method of a nano particle based on polyamino acid. The preparation method of the nano particle based on the polyamino acid comprises the following steps of firstly adopting a hydrophobic hydroxy compound and p-nitro benzyl chloride acid ester as raw materials, and reacting to obtain a functional hydrophobic micromolecule activated by the p-nitro benzyl chloride acid ester; then adopting the functional hydrophobic micromolecule activated by the p-nitro benzyl chloride acid ester and a diamine compound as reactants, and reacting to preparing a hydrophobic amido compound; adopting the hydrophobic amido compound as an initiator, carrying out ring opening polymerization on alpha-amino acid-N-thiocarboxy anhydride compound to obtain a polymer based on the polyamino acid; finally dissolving the polymer based on the polyamino acid in water, then adding an acetone solution of the polymer, and stirring to obtain the functional biodegradable nano particle based on the polyamino acid. The obtained drug-loading targeting nano particle has higher stability, can be combined with targeting molecules so as to well gather to a tumor location, and has good therapeutical effect and low toxic and side effect on various solid tumors including human breast cancer.

Description

technical field [0001] The invention relates to a polymer particle, in particular to a preparation method of polyamino acid-based functional biodegradable nanoparticles. 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 emulsification-solvent evaporation method or nanoprecipitation method, which usually use surfactants to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/48A61K9/14A61K31/337A61K31/355A61K31/37A61K31/4745A61K31/475A61K31/575A61K47/34C08G69/10C08G69/48A61P35/00
CPCA61K9/146A61K31/337A61K31/355A61K31/37A61K31/4745A61K31/475A61K31/575A61K47/34C08G69/10C08G69/48
Inventor 邓超武金田孟凤华钟志远
Owner ZHANGJIAGANG INST OF IND TECH SOOCHOW UNIV
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