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A selective copper ion chelating agent, its preparation method and its application in colorectal cancer

A technology of copper ions and chelating agents, applied in the field of medicine, can solve the problems of poor selectivity of chelating agents, and achieve the effects of enhanced specificity, low cytotoxicity, and novel structure

Active Publication Date: 2022-05-17
AFFILIATED HOSPITAL OF JINING MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these copper ion chelating agents used clinically are poor in selectivity, and they can coordinate and chelate with other metal ions while chelating copper ions.

Method used

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  • A selective copper ion chelating agent, its preparation method and its application in colorectal cancer
  • A selective copper ion chelating agent, its preparation method and its application in colorectal cancer
  • A selective copper ion chelating agent, its preparation method and its application in colorectal cancer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] The synthesis of embodiment 1 compound JYFY-001

[0054] (1) Acetic acid (0.24g, 4.0mmol), DMAP (0.49g, 4.0mmol) and EDCI (0.77g, 4.0mmol) were added to 6mL CH 2 Cl 2 , stirred at room temperature for 10 min. After adding 2-bromothieno[3,2-c]pyridin-4-amine (compound 1) (0.46 g, 2.0 mmol), the reaction was continued to stir at room temperature for 6 h. Spin dry CH 2 Cl 2 , added ethyl acetate, washed twice with water, and washed once with saturated NaCl solution. Anhydrous Na 2 SO 4 After drying, filter, concentrate under reduced pressure, and perform silica gel column chromatography (dichloromethane:methanol=100:1) to obtain white powdery solid N-(2-bromothieno[3,2-c]pyridin-4-yl ) Acetamide (Intermediate 2) 0.43g, yield 79.3%. Melting point: 178-180°C; 1 H NMR (400MHz, DMSO) δ8.42 (d, J = 5.5Hz, 1H), 8.16 (d, J = 5.5Hz, 1H), 7.84 (s, 1H), 2.19 (s, 3H); 13 C NMR (100MHz, DMSO) δ172.32, 150.56, 146.42, 142.87, 134.16, 124.78, 118.94, 118.72, 26.53; HRMS (ESI...

Embodiment 2

[0056] Embodiment 2 metal ion chelation experiment

[0057] (1) Experimental method:

[0058] With compound JYFY-002, compound JYFY-003 as contrast, compound JYFY-001 is carried out experimental test to the chelating ability of metal ion, and the name of described compound JYFY-002, compound JYFY-003 is N-(2-(pyridine -3-yl)thieno[3,2-c]pyridin-4-yl)cyclopropylformamide (compound JYFY-002), N-(2-(5-phenylpyridin-3-yl)thieno [3,2-c]pyridin-4-yl)cyclopropylformamide (compound JYFY-003), the structural formula of compound JYFY-002 and compound JYFY-003 is as follows:

[0059]

[0060] The metal chelating ability of compounds JYFY-001, JYFY-002 and JYFY-003 was detected by UV-Vis spectrophotometer. Incubate the methanol solution containing the compound to be tested (20 μM) or the compound (20 μM) and metal ions (40 μM) at 25° C. for 30 min, and detect its absorption spectrum at a wavelength of 200-500 nm.

[0061] (2) Experimental results:

[0062] like Figure 4 , Fig...

Embodiment 3

[0063] Example 3 Colorectal cancer cell proliferation inhibition experiment

[0064] (1) Experimental method:

[0065] SW620 and HCT116 colorectal cancer cells were cultured in RPMI Medium1640 medium containing 10% FBS and 1% penicillin and streptomycin. Inoculate 100 μL medium containing SW620 and HCT116 on a 96-well cell culture plate, each well containing 1×10 4 cells. 96-well cell culture plate placed in 5% CO 2 , and cultivated in a constant temperature incubator at 37°C for 12h. Then, 100 μL of compound medium solutions with final concentrations of 100, 50, 25, 12.50, 6.25, 3.13, 1.56, 0.78, and 0.39 μM were added to the respective culture wells, and the culture was continued for 48 h. Add 10 μL of CCK8 solution to each well and continue to incubate for 1 h. After shaking, the light absorption value (OD value) at a wavelength of 450 nm was measured with a microplate reader. Under the same conditions, 100 μL of medium containing 1 μL DMSO was added as a control. ...

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Abstract

The invention discloses a selective copper ion chelating agent, its preparation method and its application in colorectal cancer. The chelating agent is N-(2-(pyridin-3-yl)thieno[3,2-c ]pyridin-4-yl)acetamide. Cu of the present invention + / Cu 2+ The chelating agent JYFY‑001 has a novel structure, and can inhibit the proliferation of colorectal cancer SW620 and HCT116 cells by specifically chelating copper ions enriched in colorectal cancer cells; it has shown a good ability to inhibit HCT116 microspheres; Lower toxicity to normal cells. The invention provides a compound capable of inhibiting the proliferation of colorectal cancer cells, microspheres of colorectal cancer cells and lower normal cytotoxicity. important meaning.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a selective copper ion chelating agent, its preparation method and its application in colorectal cancer. Background technique [0002] Colorectal cancer (CRC) is a common malignant tumor of the digestive system that occurs in the colorectum. The incidence rate ranks third among malignant tumors, and the mortality rate ranks second. The early symptoms of colorectal cancer are not obvious, and most patients have developed into the middle and late stages when symptoms such as blood in the stool, change in bowel habits, weight loss, and anemia appear. The pathogenesis of colorectal cancer is not yet fully understood, but it is currently known to be related to genetic factors, environmental factors and chronic inflammation. [0003] Copper is an essential trace element for the human body. More and more evidences have confirmed that the disorder of copper ion level can induce tumo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04A61P35/00A61K31/444
CPCC07D495/04A61P35/00Y02P10/20
Inventor 石小龙刘艳荣李莹贾孟亭孙涛张苗苗寻情情
Owner AFFILIATED HOSPITAL OF JINING MEDICAL UNIV
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