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A kind of sulfur-containing aminoalcohol Schiff base copper complex and its preparation and application

A technology of thioaminoalcohol and Schiff base copper, which is applied in the direction of copper organic compounds, drug combinations, antineoplastic drugs, etc.

Active Publication Date: 2020-09-25
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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  • A kind of sulfur-containing aminoalcohol Schiff base copper complex and its preparation and application
  • A kind of sulfur-containing aminoalcohol Schiff base copper complex and its preparation and application
  • A kind of sulfur-containing aminoalcohol Schiff base copper complex and its preparation and application

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 crystal

[0026]Dissolve L-methioninol with anhydrous methanol to prepare L-methioninol anhydrous methanol solution with a concentration of 0.1mmol / mL; dissolve KOH solid with anhydrous methanol to prepare a KOH anhydrous solution with a concentration of 0.05mmol / mL methanol solution. In a 25mL reactor, 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, magnetically stirred the solution at room temperature to form a vortex, the solution was egg yellow. After stirring for 1 h, Cu(NO 3 ) 2 ·3H 2 O (0.1216g, 0.5mmol) and 6mL of anhydrous methanol were stirred for 1h, and a green liquid with a small amount of turbidity was obtained. After the stirring is stopped, tighten the lid of the reaction kettle and place it in a blast oven with a constant temperature. The reactor is kep...

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 ] Dissolve the single crystal with DMSO first, then slowly add ethanol to form a solution with DMSO-ethanol (volume ratio 1:1) mixed solvent, the final concentration is 2.0mmol.L -1 , detected by transmission electron microscope, it was observed that [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 ]In vitro cytotoxicity test of nanoparticles

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

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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 their preparation, in particular to a sulfur-containing amino alcohol Schiff base copper complex and its preparation method and application. Background technique [0002] Cancer treatment has always been facing severe challenges. Cisplatin has been clinically used to treat tumors, but the toxicity and side effects of cisplatin are significant, and it shows significant drug resistance. Tumor growth, progression, invasion and metastasis are closely related to tumor angiogenesis. Malignant tumors can derive their own vasculature to obtain nutrition, and after tumor cells obtain nutrition, 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 induci...

Claims

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Application Information

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Patent Type & Authority Patents(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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