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Binuclear cadmium complex with anticancer activity as well as preparation method and application thereof

A technology for cadmium complexes and anticancer activity, applied in the field of binuclear cadmium complexes and their preparation, can solve the problem that biological activity research is rare, and achieve significant antitumor cell activity, good luminescence performance, and good π-conjugation flat effect

Active Publication Date: 2022-07-01
ZHONGSHAN POLYTECHNIC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The acylhydrazone Schiff base cadmium complexes have a wide range of application prospects, including catalysis, luminescent probes, and molecular sensors. Currently, there are few studies on the biological activity of acylhydrazone cadmium (III) complexes.

Method used

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  • Binuclear cadmium complex with anticancer activity as well as preparation method and application thereof
  • Binuclear cadmium complex with anticancer activity as well as preparation method and application thereof
  • Binuclear cadmium complex with anticancer activity as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] In the present embodiment, hydrazine hydrate selects 50% hydrazine hydrate supplied by Sinopharm Chemical Reagent Co., Ltd., methyl 4-fluorobenzoate selects 99% methyl 4-fluorobenzoate supplied by Sinopharm Chemical Reagent Co., Ltd., and methanol selects Sinopharm Analytical pure methanol supplied by Group Chemical Reagent Co., Ltd., 99% o-vanillin supplied by Sinopharm Group Chemical Reagent Co., Ltd. for o-vanillin, analytical pure ethanol supplied by Sinopharm Group Chemical Reagent Co., Ltd., cadmium nitrate tetrahydrate selected Analytical pure cadmium nitrate tetrahydrate supplied by Sinopharm Chemical Reagent Co., Ltd., N,N-dimethylformamide selected 99.8% N,N-dimethylformamide supplied by Sinopharm Chemical Reagent Co., Ltd., the following example 2- 7 All use the reagents in Example 1.

Embodiment 2

[0038] Example 2 A dinuclear cadmium complex with anticancer activity bis-[4-fluoro-N'-(2-hydroxy-3-methoxybenzylidene) benzohydrazide]. cadmium dinitrate (Cd- F-L) and its preparation

[0039] S1. Synthesis of Hydrazide Compounds:

[0040] The hydrazine hydrate solution of 0.06mol 50% was slowly dropped into the mixture of methanol 30ml and 0.02mol methyl 4-fluorobenzoate, heated to reflux, cooled to room temperature after refluxing and added ice water, the first precipitation

[0041] After the material appeared, it was filtered, dried and recrystallized from methanol, and dried at 50 °C to obtain 4-fluorobenzoic hydrazide with a yield of 88.31%;

[0042] S2. Organic Ligand Synthesis:

[0043] To a 100ml round-bottomed flask, add 10mmol of 4-fluorobenzoic hydrazide and 10mmol of o-vanillin, add 40ml of ethanol, heat to reflux, after refluxing, cool down to room temperature, filter, collect the second precipitate, and wash the first precipitate with methanol. Diprecipitate...

Embodiment 3

[0054] Example 3 Binuclear cadmium complex bis-[N'-(2-hydroxy-3-methoxybenzylidene)-4-(1,2,2-triphenylvinyl)benzyl with anticancer activity Hydrazide]. Cadmium dinitrate (Cd-TPE-L) and its preparation

[0055] S1. Synthesis of Hydrazide Compounds:

[0056] Slowly drop 10mmol of 50% hydrazine hydrate solution into a mixture of 50ml of methanol and 10mmol of methyl 4-(1,2,2-triphenylvinyl)-benzoate, reflux at 70°C for 10h, and cool after refluxing. After reaching room temperature, the first precipitate appeared, filtered, dried and recrystallized from methanol, and dried at 50°C to obtain 4-tetrastyrylcarboxylic acid hydrazide;

[0057] S2. Organic Ligand Synthesis:

[0058] Add 2mmol of 4-tetrastyrylcarboxylic acid hydrazide and 2mmol of o-vanillin to a 100ml round-bottomed flask, add 30ml of ethanol, heat to reflux, after refluxing, cool to room temperature, filter, collect the second precipitate, use The second precipitate was washed 1~2 times with methanol, and dried at 5...

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Abstract

The invention discloses a binuclear cadmium complex with anticancer activity as well as a preparation method and application thereof. The binuclear cadmium complex is an infinite network structure material formed by connecting cadmium salt and an organic ligand in a coordination bond manner, the binuclear cadmium complex is di-[4-fluoro-N '-(2-hydroxyl-3-methoxybenzylidene) benzoyl hydrazine], or di-[N'-(2-hydroxyl-3-methoxybenzylidene)-4-(1, 2, 2-triphenylvinyl) benzoyl hydrazine], or di-[N '-(2-hydroxyl-3-methoxybenzylidene)-4-(1, 2, 2-triphenylvinyl) benzoyl hydrazine], or di-[N'-(2-hydroxyl-3-methoxybenzylidene)-4-(1, 2, 2-triphenylvinyl) benzoyl hydrazine]. The binuclear cadmium complex disclosed by the invention takes a binuclear planar cadmium unit as a metal ligand, is assembled into a metal organic framework with a stable planar structure, has relatively strong tumor cell apoptosis inducing capability on human breast cancer cells and human lung cancer cells, and also has remarkable tumor cell resisting activity. Therefore, the binuclear cadmium complex provided by the invention is a promising material for developing novel anti-tumor drugs, and has a relatively high application value in developing the anti-tumor drugs.

Description

technical field [0001] The invention belongs to the technical field of metal-organic framework materials, and in particular relates to a dual-nuclear cadmium complex with anticancer activity and a preparation method and application thereof. Background technique [0002] Metal complexes have been extensively studied because of their tunable structures and positive charges, which are very favorable for their interaction with the phosphate backbone of DNA. These research works have broadened the knowledge field of the biochemistry of the interaction between metal complexes and DNA to a certain extent, but such research is currently mainly focused on mononuclear metal complexes, as opposed to planar binuclear metal complexes. Objects have less work. Therefore, designing and synthesizing planar binuclear metal complexes targeting DNA can provide another broad space for the development of new anti-tumor and anti-cancer drugs. [0003] Acylhydrazones are a class of Schiff base or...

Claims

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Application Information

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IPC IPC(8): C07F3/08C07C241/04C07C243/38C07C249/16C07C251/86C09K11/06A61P35/00
CPCC07F3/003C07C241/04C07C249/16C09K11/06A61P35/00C09K2211/188C07B2200/13C07C243/38C07C251/86
Inventor 王俊柯静萍聂建华侯勇陈家贺陈振冲吴镇艺钟晓娜陈远航梁皓泓
Owner ZHONGSHAN POLYTECHNIC
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