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Acylhydrazone schiff base-copper complex-human serum albumin complex and applications thereof

A technology of acylhydrazone Schiff base copper and human serum albumin, applied in the field of pharmaceuticals, can solve the problems of premature release of metal prodrugs, inability to reach cancer cells, side effects, etc., to achieve not easy to be swallowed, good anticancer activity, Effect of Narrow Particle Size Distribution

Active Publication Date: 2017-05-31
苏州美仑生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, there are two possible disadvantages of HSA carrier carrying metal prodrugs to cancer cells in vivo
First, the metal prodrug is attached to the surface of HSA, which causes the drug to be exposed to other proteins in the body, so that these proteins may compete with HSA for binding the drug, causing the metal prodrug to escape from the HSA carrier and bind to other proteins, which may cause side effects
Second, since metal prodrugs bind too weakly to HSA, metal prodrugs may be released prematurely and fail to reach cancer cells

Method used

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  • Acylhydrazone schiff base-copper complex-human serum albumin complex and applications thereof
  • Acylhydrazone schiff base-copper complex-human serum albumin complex and applications thereof
  • Acylhydrazone schiff base-copper complex-human serum albumin complex and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1 Preparation and characterization of the acylhydrazone Schiff base copper complex [CuBr(BA)(L)] (compound C1) and [CuBr(DMF)(L)] (compound C2) of the present invention

[0049] The acylhydrazone Schiff base ligand L used in the present invention is based on (E)-N'-(5-chloro-2-hydroxybenzylidene) benzoylhydrazide Schiff base (references: Ali HM, Puvaneswary S, Ng SW.5-Chlorosalicylaldehydebenzoylhydrazone.Acta Crystallogr., Sect.E: Struct.Rep.Online 2005,61,o2415.) as an example to prepare the acylhydrazone Schiff base copper complex.

[0050] [CuBr(BA)(L)](C1) was synthesized as follows: L (0.55 g, 2 mmol) and the heterocyclic nitrogen ligand quinoline (BQAL; 0.26 g, 2 mmol) were dissolved in 15 mL of methanol and stirred at room temperature for 1 h , an orange-yellow liquid was obtained. Then add CuBr dissolved in methanol 2 (0.44g, 2mmol) solution. The above mixed solution was stirred at room temperature for another 1 h to obtain a dark green solution, and...

Embodiment 2

[0063] Example 2 Preparation and Characterization of Acylhydrazone Schiff Base Copper Complex-Human Serum Albumin Complex (HSA-C1 / C2)

[0064] Take 10ml of 20% medical human serum albumin, 2g powdered activated carbon and 5ml ultrapure water in a 50ml beaker, place the beaker in ice water, adjust the pH to 2.8, stir for 2h, then adjust the pH to 7.5. Then centrifuge and dialyze to remove activated carbon, dimers and polymers in HSA to obtain monomeric HSA used in subsequent experiments.

[0065] Single crystal diffraction of HSA complexes: Fatty acid (PA) was diluted to 2.5 mM with 20 mM potassium phosphate (pH 7.5). In the experiment, in order to combine C1 and C2 with HSA to form a prodrug complex, first mix 380 μL of PA (2.5 mmol), 100 μL of HSA (100 mg / mL), and 90 μL of Cu complex (5 mmol), and then Incubate for 24 hours, and finally put the mixture in a concentrator tube, wash with water, filter and concentrate to 100 mg / ml (microporous spin filter (10,000 Dalton cut-off...

Embodiment 3

[0074] Example 3 Preparation and Characterization of Acylhydrazone Schiff Base Copper Complex-Human Serum Albumin Complex-Folic Acid Nanoparticles (FA-HSA-C1 / C2)

[0075] (1) Preparation of Acylhydrazone Schiff Base Copper Complex-Human Serum Albumin Complex-Folic Acid Nanoparticles (HSA-C1 / C2 NPs)

[0076] In order to obtain the HSA-metal prodrug and a constant drug loading ratio, first the acylhydrazone Schiff base copper complex of the present invention prepared in Example 1 was incubated with HSA at room temperature (molar ratio 1:3) for 24h, and the excess The acylhydrazone Schiff base copper complex is removed by centrifugal dialysis. Next, according to the desolvation method in the literature, at room temperature and under constant stirring, adjust the pH of 4 mL of the above-incubated acylhydrazone Schiff base copper complex and HSA mixture (1.5 mM) to 8, and continuously add 15.0 mL of ethanol solution (1mL / min), gradually forming HSA-C1 / C2 NPs. After protein denatu...

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Abstract

The invention discloses an acylhydrazone schiff base-copper complex and complex nanoparticles composed of the acylhydrazone schiff base-copper complex and human serum albumin. The chemical formula of the acylhydrazone schiff base-copper complex is [CuBr(BA)(L)] or [CuBr(DMF)(L)], wherein BA is quinoline, L is a compound with a tridentate acylhydrazone schiff base structure, DMF is N,N-dimethyl formamide, and Br-, quinolone or DMF in the complex is coordinated with a copper center as ligands. As prodrugs, the complex nanoparticles composed of the acylhydrazone schiff base-copper complex and human serum albumin not only improve the activity of drugs, but also can reduce the toxicity of drugs, thus having good clinical application values.

Description

technical field [0001] The invention belongs to the field of pharmacy, and in particular relates to an acylhydrazone Schiff base copper complex, an acylhydrazone Schiff base copper complex-human serum albumin complex and its application in the preparation of prodrugs. Background technique [0002] According to GLOBOCAN estimates, there were approximately 1.7 million new breast cancer cases and 521,900 breast cancer deaths worldwide in 2012, and an estimated 21.4 million new cancer cases and approximately 13.2 million cancer deaths will increase globally by 2030. Although traditional cancer chemotherapy has been quite beneficial in improving survival over the past decades, it has also shown many adverse effects, including limited efficacy, nonspecificity, multidrug resistance, and adverse side effects. To overcome these obstacles, various approaches have been developed, including prodrug strategies and nanoparticle drug delivery strategies. [0003] Currently, the developmen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/08A61K31/555A61K47/69A61K47/54A61K47/62A61P35/00A61P3/12
CPCC07F1/005C07F1/08
Inventor 苟峄杨峰
Owner 苏州美仑生物科技有限公司
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