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PH-GSH dual-responsiveness 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 low drug loading rate, and achieve good application and development prospects, high drug loading, and improved The effect of water solubility

Active Publication Date: 2020-09-08
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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  • PH-GSH dual-responsiveness nano curcumin prodrug loading system
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  • PH-GSH dual-responsiveness nano curcumin prodrug loading system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1: the synthesis of compound 2

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

[0047]

[0048] Accurately weigh 1,4-dimethoxybenzene (0.691g, 5mmol) and paraformaldehyde (0.450g, 15mmol) into a 100mL round bottom flask, add 60mL of 1,2-dichloroethane to dissolve. Then boron trifluoride diethyl ether (0.75ml, 6mmol) was added to the above solution, stirred at room temperature for 2h under nitrogen protection, and ice water was added to quench the reaction after the reaction was completed. Atmospheric filtration, followed by removal of solvent using a rotary evaporator. The residue was dissolved in dichloromethane (DCM), washed three times with deionized water, saturated NaHCO3 solution, and saturated NaCl solution, and the organic phase was collected and dried with anhydrous MgSO4 for 2 h, filtered, and evaporated under reduced pressure to remove the organic solvent. The crude product can be obtained and separated by column chromatography (pet...

Embodiment 2

[0049] Embodiment 2: the 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 bottom 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. (This compound is unstable, after the selection is obtained, go to the next step directly).

Embodiment 3

[0053] Embodiment 3: the 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 (1.658g, 12mmol), stirred at room temperature for 30min. Then ethyl bromoacetate (2 mL, 18 mmol) and KI (0.166 g, 1 mmol) were added, and refluxed for 24 h under nitrogen protection. Treat that reaction finishes, after solution cools down naturally, filter to remove unnecessary K 2 CO3, and the solvent was removed using a rotary evaporator. The residue was redissolved in DCM, washed three times with deionized water and saturated NaCl solution, and the organic phase was collected and washed with anhydrous NaCl 2 SO4 dried for 2h. Filter under normal pressure and distill off the organic solvent under reduced pressure to obtain the crude product, which can be separated by column chromatography (dichloromethane / methanol, v / v=50:1) to obtain or...

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Abstract

The invention discloses a pH-GSH dual-responsiveness nano curcumin prodrug loading system. A water-soluble column [5] arene with pH responsiveness is used as a main body molecule; a disulfide bond with GSH responsiveness and a pyridinium modified phenylboronic acid derivative are used as guest molecules; curcumin and the phenylboronic acid derivative form a boron ester bond with pH stimulus response, and the boron ester bond is modified on a guest molecule; amphiphilic curcumin prodrug molecules are formed through host-guest complexation, then the amphiphilic curcumin prodrug molecules are self-assembled in an aqueous solution to form nano particles by utilizing hydrophilic and hydrophobic effects, and the pH-GSH double-responsiveness nano curcumin prodrug system is obtained. The pH-GSH dual-responsiveness nano curcumin prodrug loading system can be applied to transportation of anti-cancer drugs to achieve the purpose of drug combination, solves problems of single drug use and single stimulus response in a nano drug delivery system, meets the development requirements of the current society, and has good application and development prospects.

Description

technical field [0001] The invention belongs to the field of nano-biological medical materials, relates to a drug-carrying system and its preparation, in particular to a pH-GSH double-responsive nano-curcumin prodrug-carrying system. Background technique [0002] Studies have shown that in cancer treatment, most anticancer drugs have poor water solubility, low utilization rate, and toxic side effects on normal cells, which have always been difficult problems in the chemotherapy process. Therefore, the structural design and modification of small molecule anticancer drugs with poor water solubility, and the protection of their active groups to form prodrug molecules 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 release or less release in normal cells, th...

Claims

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Application Information

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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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