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A ph-gsh dual-responsive nano-curcumin prodrug loading system

A curcumin-based, responsive technology, applied in the field of nano-biomedical materials, can solve the problems of low drug release rate, complex system structure, and single stimulus response, and achieve good application and development prospects, high drug loading, and improved water solubility. sexual effect

Active Publication Date: 2022-07-15
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the use of polymers to construct prodrug delivery systems has complex architecture, low drug loading rate, and single stimulus response, resulting in low drug release rate. system is of great significance

Method used

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  • A ph-gsh dual-responsive nano-curcumin prodrug loading system
  • A ph-gsh dual-responsive nano-curcumin prodrug loading system
  • A ph-gsh dual-responsive nano-curcumin prodrug loading system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1: Synthesis of Compound 2

[0046] The synthetic route of compound 2 is as follows:

[0047]

[0048] Accurately weigh 1,4-dimethoxybenzene (0.691 g, 5 mmol) and paraformaldehyde (0.450 g, 15 mmol) into a 100 mL round-bottomed flask, and add 60 mL of 1,2-dichloroethane to dissolve. Then, boron trifluoride ether (0.75 ml, 6 mmol) was added to the above solution, and the mixture was stirred at room temperature for 2 h under nitrogen protection. After the reaction was completed, ice water was added to quench the reaction. Filter at atmospheric pressure, then use a rotary evaporator to remove the solvent. The residue was dissolved in dichloromethane (DCM), washed 3 times with deionized water, saturated NaHCO solution and saturated NaCl solution, respectively, the organic phase was collected and dried with anhydrous MgSO for 2 h, filtered, and the organic solvent was removed by distillation under reduced pressure, The crude product can be obtained and separated...

Embodiment 2

[0049] Example 2: Synthesis of Compound 3

[0050] The synthetic route of compound 3 is as follows:

[0051]

[0052] Accurately weigh compound 2 (0.660 g, 0.88 mmol) into a 50 mL round-bottomed flask, add 20 mL of dry DCM to dissolve, add boron tribromide (4 mL, 43 mmol) dropwise, and stir at room temperature for 24 h under nitrogen protection. After the reaction was completed, ice water was added to quench the reaction. After adding ice water and stirring for 30 min, the white solid was obtained by suction filtration and washed with 1 mmol / L hydrochloric acid and chloroform to obtain compound 3. (The compound is not stable, after selection, proceed directly to the next step).

Embodiment 3

[0053] Example 3: Synthesis of Compound 4

[0054] The synthetic route of compound 4 is as follows:

[0055]

[0056] Compound 3 (0.610 g, 1 mmol) was dispersed in 30 mL of acetonitrile, and K was added to the suspension 2 CO3 (1.658 g, 12 mmol) was stirred at room temperature for 30 min. Then, ethyl bromoacetate (2 mL, 18 mmol) and KI (0.166 g, 1 mmol) were added, and the mixture was refluxed for 24 h under nitrogen protection. After the reaction is over, the solution is cooled naturally and filtered to remove excess K 2 CO3, then the solvent was removed using a rotary evaporator. The residue was redissolved in DCM, washed three times with deionized water and saturated NaCl solution, respectively, the organic phase was collected and washed with anhydrous Na 2 SO4 dried for 2h. After filtration at normal pressure, after the organic solvent was distilled off under reduced pressure, the crude product was obtained, and the orange solid 4 was obtained by column chromatogra...

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Abstract

The invention discloses a pH-GSH dual-responsive nanometer curcumin prodrug drug-carrying system. A pH-responsive water-soluble column[5]arene is used as the main molecule, and a GSH-responsive disulfide bond and pyridine are used as the main molecule. The salt-modified phenylboronic acid derivative is a guest molecule, and curcumin is modified to the guest molecule by forming a boronic ester bond with pH stimulation response with the phenylboronic acid derivative. After host-guest complexation, the amphiphilic curcumin is formed. drug molecules, and then the amphiphilic curcumin prodrug molecules are self-assembled in an aqueous solution to form nanoparticles by utilizing hydrophilic and hydrophobic interactions to obtain a pH-GSH dual-responsive nanometer curcumin prodrug system. It can be used for the transportation of anticancer drugs to achieve the purpose of combined medication. The problem of single drug and single stimulus response in the nano-drug loading system is solved, which meets the development requirements of today's society and has good application and development prospects.

Description

technical field [0001] The invention belongs to the field of nanometer biomedical materials, relates to a drug-carrying system and its preparation, and in particular relates to a pH-GSH dual-responsive nanometer curcumin prodrug drug-carrying system. Background technique [0002] Studies have shown that in cancer treatment, most anticancer drugs have poor water solubility, low utilization, and toxic side effects on normal cells. Therefore, structural design and modification of small molecule anticancer drugs with poor water solubility, and their active groups are protected to form prodrug molecules, which can improve the water solubility of hydrophobic drugs; the difference between the internal microenvironment of cancer cells and normal cells, Such as lower pH, higher concentration of glutathione (GSH), etc., can stimulate prodrug molecules to release active drugs, but no or less release in normal cells, thereby reducing the toxic side effects of drugs on normal cells . ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/69A61K47/54A61K31/12A61P35/00
CPCA61K47/6949A61K47/54A61K31/12A61P35/00
Inventor 裴志超沈紫嫣裴玉新吕秀凯晁爽
Owner NORTHWEST A & F UNIV
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