Targeted dual-stimuli-responsive multifunctional ceria nano-drug loading system encapsulated with degradable polydopamine

A stimuli-responsive, ceria-based technology, applied in the field of nano-biomedical materials, can solve problems such as retention, achieve rapid release, increase lethality, good application and development prospects

Active Publication Date: 2021-05-07
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, Insung S. Choi's research group only stopped at the synthesis of polydopamine containing disulfide bonds, and did not fully apply it

Method used

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  • Targeted dual-stimuli-responsive multifunctional ceria nano-drug loading system encapsulated with degradable polydopamine
  • Targeted dual-stimuli-responsive multifunctional ceria nano-drug loading system encapsulated with degradable polydopamine
  • Targeted dual-stimuli-responsive multifunctional ceria nano-drug loading system encapsulated with degradable polydopamine

Examples

Experimental program
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Effect test

preparation example Construction

[0031] The preparation method of the targeted stimulus-responsive multifunctional ceria nano-loading system includes the following steps:

[0032] 1) Synthesis of dopamine derivative monomers containing disulfide bonds;

[0033] 2) Porous ceria adsorbs medicine;

[0034] 3) Put the dopamine derivative containing disulfide bond and the cerium oxide adsorbing the drug in the alkaline Tris-HCl solution and stir to form a degradable polydopamine film on the surface of the ceria, and then the sugar with hydroxyl Placed in the drug-loading system, the sugar with hydroxyl groups is connected by Michael addition or Schiff base reaction, and a targeted dual-stimuli-responsive multifunctional ceria nanometer drug-loading system encapsulated by degradable polydopamine is constructed.

[0035] Since the surface of the porous ceria nanorods is coated with degradable polydopamine, the biocompatibility of the system can be significantly improved; at the same time, the sugar with hydroxyl gr...

Embodiment 1

[0039]

[0040] Compound 2: Levodopa (274.5 mg, 1.39 mmol) and TBDMSCl (638 mg, 4.23 mmol) were dissolved in 2 mL of dry acetonitrile, DBU (602.8 mg, 4 mmol) was added dropwise at 0°C for 10 min, and stirred at room temperature for 24 h. After filtration, the filter residue was recrystallized from methanol / acetonitrile to obtain 425.7 mg of pure compound 2 with a yield of 81%.

[0041] 1 H NMR (500MHz, CD 3OD): δ6.84(dd, J=14.0, 5.0Hz, 2H), 6.77(dd, J=8.1, 1.9Hz, 1H), 3.69(dd, J=9.0, 4.0Hz, 1H), 3.21(dd , J=14.7, 3.9Hz, 1H), 2.86(dd, J=14.6, 9.1Hz, 1H), 1.01(d, J=4.6Hz, 18H), 0.23(d, J=2.2Hz, 6H), 0.20 (s,6H) ppm.

Embodiment 2

[0043]

[0044] Synthesis of Compound 3: Compound 2 was added to 1 mL containing 15.5 mg NaHCO 3 deionized water, and then add 1 mL of tetrahydrofuran containing di-tert-butyl dicarbonate. After stirring at room temperature for 24 hours, THF was rotary evaporated, added pure water and extracted with ether. The aqueous layer was acidified with citric acid to pH=5-6 and then extracted with ether for 3 times. The organic phase was dried over magnesium sulfate. Finally, 66 mg of yellow oily liquid was obtained by column chromatography with a yield of 74%.

[0045] 1 H NMR (500MHz, CD 3 OD): δ6.76(t, J=5.3Hz, 2H), 6.69(d, J=8.1Hz, 1H), 4.29(dd, J=8.2, 4.9Hz, 1H), 3.02(dd, J=13.9 , 4.8Hz, 1H), 2.80(dd, J=13.8, 8.7Hz, 1H), 1.40(s, 9H), 0.99(d, J=6.2Hz, 18H), 0.21(d, J=1.8Hz, 6H ), 0.18 (s, 6H) ppm.

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Abstract

The invention relates to a degradable polydopamine-encapsulated targeted dual-stimuli-responsive multifunctional ceria nanometer drug-loading system, which uses cytotoxic ceria as the drug-loading body and polydopamine derivatized with disulfide bonds. The drug is used as the encapsulation of the drug, so that the drug is encapsulated on the drug-loaded body, and at the same time, the sugar with a hydroxyl group is used as the targeting group, and is connected to the surface of the system through Michael addition or Schiff base reaction. The sugars with hydroxyl groups attached to the surface of polydopamine can significantly improve the biocompatibility of the system; the sugars with hydroxyl groups can interact with specific lactose-binding proteins overexpressed on the surface of cancer cells to achieve targeted selective entry Cancer cells, the acidic internal environment of cancer cells can slowly degrade polydopamine, use the high concentration of GSH in cancer cells to promote the rapid breaking of the disulfide bond in polydopamine, and accelerate the rapid degradation of polydopamine to achieve rapid release of anticancer drugs , to realize the synergistic anticancer effect of cerium oxide nanocarriers and anticancer drugs.

Description

technical field [0001] The invention belongs to the field of nano biomedical materials, and in particular relates to a degradable polydopamine-encapsulated targeted dual-stimuli-responsive multifunctional ceria nanometer drug-carrying system. Background technique [0002] Cancer is still one of the most harmful diseases in the world. The main methods of cancer treatment include surgery, radiation therapy and chemical drug therapy. Chemotherapy is currently the main means of cancer treatment, but chemotherapy has problems such as low drug utilization and damage to normal tissue cells. Therefore, the development of a nano drug delivery system is the most economical and effective means to reduce the toxic effect of drug molecules and increase the concentration of drugs in tumor tissues. Among the many new drug carriers, the polydopamine-based nano-drug delivery system has become an ideal drug carrier due to its good biocompatibility and superior performance such as degradabili...

Claims

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Application Information

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Patent Type & AuthorityPatents(China)
IPC IPC(8): A61K47/54A61K47/69A61K9/51A61K47/02A61K47/34A61K31/704A61P35/00
CPCA61K9/5115A61K9/5146A61K31/704
Inventor裴玉新张营吴晓文裴志超卢玉超
OwnerNORTHWEST A & F UNIV