Efficient metal-containing cationic antitumor drug as well as preparation method and application thereof

A metal cation, divalent metal technology, applied in anti-tumor drugs, medical preparations containing active ingredients, drug combinations, etc. The effect of inhibiting tumor metastasis

Pending Publication Date: 2021-06-25
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But cancer cells have a good mechanism to pump these drugs out of the cell, thus developing strong drug resistance

Method used

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  • Efficient metal-containing cationic antitumor drug as well as preparation method and application thereof
  • Efficient metal-containing cationic antitumor drug as well as preparation method and application thereof
  • Efficient metal-containing cationic antitumor drug as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Dodecyl alcohol (3.72 g, 0.02 mol) and triethylamine (2.02 g, 0.02 mol) were added to a 100 mL flask. Acryloyl chloride (2.02 g, 0.02 mol) was dissolved in dichloromethane (50 mL). Add the acryloyl chloride solution to the reaction solution with a constant pressure dropping funnel within 30 minutes and keep it overnight at 20°C. The reaction solution was washed three times with pure water to remove most of the triethylamine hydrochloride, dried and concentrated, and then purified on a silica gel column (ethyl acetate / petroleum ether 10:1) to obtain farnesol acrylate.

[0055]The compound of formula III (n=2) (0.726g, 0.003mol), lauryl acrylate (2.40g, 0.01mol) and triethylamine (0.606g, 0.006mol) were added in 3.0mL DMF, under argon The reaction was carried out at 90° C. for 48 h in a sealed tube under atmosphere. After being separated by a silica gel column (dichloromethane / methanol 10:1), the metal cation compound precursor is obtained, and its H NMR spectrum is as ...

Embodiment 2

[0059] In Vitro Antitumor Evaluation of Metal Cationic Compounds

[0060] The in vitro anti-tumor effect of metal cation compounds was measured by MTT method: cancer cells (HepG2) were pre-added to 96-well plates and cultured overnight. The metal cation compound (Formula V) was formulated to a concentration of 800 μΜ. Observed by transmission electron microscopy, the metal cation compound (formula V) forms nano micelles with uniform size. After incubating the cells for 24 hours in the presence of 10 [mu]M to 100 [mu]M metal cation compound (Formula V), the medium was aspirated off. After adding MTT and incubating for 4 hours, 100 microliters of dimethylsulfoxide (DMSO) was added to each well, which can dissolve formazan in the cells. The light absorption value was measured at a wavelength of 570nm by an enzyme-linked immunosorbent assay instrument, and the cytotoxicity calculation method corresponding to the experimental group was the ratio of ultraviolet absorption between ...

Embodiment 3

[0062] Drug Resistance Evaluation of Metal Cationic Compounds

[0063] The drug resistance evaluation of metal cation compounds was carried out by repeated stimulation with low concentration of drugs and then evaluating the change of cytotoxicity. Drug-naïve cells (HepG2) were considered as first passage cells. After the confluence of the first-generation cells reaches about 50%, they are treated with 20 micromoles of the metal cation compound (Formula V). After the cells are full, digest and divide the plate, repeat the above operation three times to obtain the second generation cells. The fifth-generation cells were obtained through repeated drug stimulation, and the toxicity of metal cation compounds to each generation of cells was measured by MTT method to evaluate the changes in the sensitivity of tumor cells to metal cation compounds. Figure 5 Cell viability of each passage is shown. From Figure 5 It can be seen from the figure that the cell viability of each gener...

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Abstract

The invention relates to a metal-containing efficient cationic antitumor drug as well as a preparation method and an application thereof. Specifically, the invention relates to metal cationic compounds of formula I wherein M is a divalent metal, n is an integer from 1 to 10, X is independently selected from O, S and NH, and R is a hydrophobic chain hydrocarbyl group. The metal cation medicine disclosed by the invention has broad-spectrum anticancer property, does not generate drug resistance, reduces toxic and side effects while improving the anti-tumor effect, and can be used for treating tumors without a carrier. In addition, the amphiphilic micromolecule structure is simple, can play a role without entering cells, does not generate drug resistance, and can inhibit tumor metastasis.

Description

technical field [0001] The invention belongs to the field of biological materials, and in particular relates to a cationic antitumor drug and its preparation method and application. Background technique [0002] Cancer is an important factor threatening human life and health. Due to the special microenvironment of cancer, there is still a lack of effective means for the prevention and control of cancer, and cancer has a major impact on people's life and health and social economy. At present, the main problem of chemotherapy is that it cannot precisely kill tumor cells selectively, and has high toxic and side effects; chemotherapy drugs flow through the whole body through blood circulation, but are less enriched in tumor sites; chemotherapy drugs are prone to multidrug resistance, that is, their It has a certain effect in the early stage of tumor treatment. After multiple treatments, tumor cells are prone to drug resistance and reduce the sensitivity of chemotherapy drugs. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/38A61K31/555A61P35/00A61P35/04
CPCC07D213/38A61P35/00A61P35/04
Inventor 尤业字聂旋张泽夏磊陈光
Owner UNIV OF SCI & TECH OF CHINA
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