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Sulfur-containing amino alcohol Schiff base copper complex, and preparation method and application thereof

A technology of thioamino alcohol and Schiff base copper, used in copper organic compounds, drug combinations, antitumor drugs, etc.

Active Publication Date: 2020-04-17
GUILIN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is reported that sulfur-containing amino acid Schiff base metal-based complexes have strong biological activity, but there are no reports on polynuclear copper-based complexes of sulfur-containing amino alcohols that have anti-tumor and anti-tumor angiogenesis

Method used

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  • Sulfur-containing amino alcohol Schiff base copper complex, and preparation method and application thereof
  • Sulfur-containing amino alcohol Schiff base copper complex, and preparation method and application thereof
  • Sulfur-containing amino alcohol Schiff base copper complex, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 [Cu 4 (C 12 H 14 N 2 O 4 S) 4 ] Preparation of single crystals

[0026]Dissolve L-methioninol with anhydrous methanol to prepare L-methioninol anhydrous methanol solution with a concentration of 0.1 mmol / mL; dissolve KOH solid with anhydrous methanol and prepare a KOH anhydrous solution with a concentration of 0.05 mmol / mL methanol solution. In the reactor of 25mL, add L-methioninol anhydrous methanol solution 2mL (0.2mmol), 5-nitrosalicylaldehyde 0.0334g (0.2mmol), KOH anhydrous methanol solution 6mL (0.3mmol) and anhydrous Methanol 8mL, stir the solution magnetically at room temperature and stir into a vortex, and the solution is egg-yellow. After stirring for 1 h, Cu(NO) was added to the solution. 3 ) 2 ·3H 2 O (0.1216 g, 0.5 mmol) and 6 mL of anhydrous methanol were stirred for 1 h to obtain a green liquid with a small amount of turbidity. After stopping stirring, tighten the lid of the reaction kettle and place it in a constant temperature blas...

Embodiment 2

[0027] Example 2 [Cu 4 (C 12 H 14 N 2 O 4 S) 4 ] Preparation of nanoparticles

[0028] will [Cu 4 (C 12 H 14 N 2 O 4 S) 4 ] The single crystal was first dissolved in DMSO, and then slowly added with ethanol to form a solution with a mixed solvent of DMSO-ethanol (volume ratio 1:1), with a final concentration of 2.0 mmol.L -1 , detected by transmission electron microscope, and observed [Cu 4 (C 12 H 14 N 2 O 4 S) 4 ] spherical nanoparticles N(TNCu-1), such as figure 2 shown.

Embodiment 3

[0029] Example 3 [Cu 4 (C 12 H 14 N 2 O 4 S) 4 ] Nanoparticles in vitro cytotoxicity assay

[0030] MTT method: Take tumor cells in logarithmic growth phase, adjust the concentration of viable cells to 5 × 10 4 100 μL per well was added to a 96-well culture plate. After culturing in the incubator for 18 hours, 100 μL of different concentrations of test samples diluted with serum-free culture were added respectively. The sample addition group was set to 6 replicate wells for each concentration. , at the same time as a negative control, placed at 37 ° C, 5% CO 2 Incubate for 48h, then add MTT (5mg / mL) 20μL / well, after 4h, use a microsyringe to gently aspirate the clear night, add dimethyl sulfoxide (DMSO) 150μL / well, shake for about 10min, use a microplate reader at 490nm wavelength OD value was determined. Calculate the cell survival inhibition rate and calculate its half inhibitory concentration IC through the software 50 .

[0031] Inhibition rate = (OD 阴性组平均值 -OD ...

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Abstract

The invention discloses a sulfur-containing amino alcohol Schiff base copper complex, and a preparation method and an application thereof. The structural formula of the copper complex is [Cu4(C12H14N2O4S)4], wherein (C12H14N2O4S)<2-> is a sulfur-containing amino alcohol Schiff base anion ligand, namely, L-2-[(5-nitro-2-hydroxyloxy-benzylidene)-amino]-4-methylthio-1-n-butyl alcohol anion. The preparation method comprises the following steps: dissolving L-methioninol in anhydrous methanol, putting the obtained solution into a reaction kettle, adding 5-nitrosalicylaldehyde, adding a potassium hydroxide-anhydrous methanol mixed solution, performing magnetic stirring the solution for 1-2 h at room temperature, adding a methanol solution of a soluble copper salt, performing magnetic stirring for0.5-1.5 h, stopping stirring, taking out a stirring bar, screwing a reaction kettle cover, placing the obtained reaction kettle in a blast constant-temperature drying box, and performing drying at the constant temperature to obtain needlelike and columnar green single crystals that are sulfur-containing amino alcohol Schiff base copper complex [Cu4(C12H14N2O4S)4] single crystals. The copper complex is not only a candidate of antitumor drugs, but also a tumor angiogenesis inhibitor.

Description

technical field [0001] The invention relates to the technical field of copper complexes and preparation thereof, in particular to a Schiff base copper complex containing a sulfur-containing amino alcohol and a preparation method and application thereof. Background technique [0002] Cancer treatment has always faced severe challenges. Cisplatin has been clinically used to treat tumors, but cisplatin has significant toxic and side effects, and shows significant drug resistance. Tumor growth, progression, invasion and metastasis are closely related to tumor angiogenesis. Malignant tumors can derive nutrients from their own vasculature, and after tumor cells obtain nutrients, they can promote tumor angiogenesis, which means that there is a mutual promotion between tumor angiogenesis and the development of malignant tumor cells. Therefore, it is of great significance to develop anti-tumor drugs with low toxicity and dual functions of inhibiting tumor angiogenesis and inducing ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/08A61P35/00
CPCA61P35/00C07F1/08
Inventor 秦秀英张佩璐磨金梅侯晓晓
Owner GUILIN MEDICAL UNIVERSITY
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