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Medical uses of methyl (E)-3-[2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-prop-2-enoate

A technology of furan dimerization of monomethyl ferulate and hydroxymethyl dihydrobenzene, which is applied in the chemical industry and can solve the problem of 3-hydroxymethyl dihydrobenzofuran dimerization of monomethyl ferulate lignin, which is rare and the like. problem, to achieve the effect of inhibiting proliferation and tumor inhibition.

Inactive Publication Date: 2013-12-04
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, reports on 3-hydroxymethyldihydrobenzofuran dimer monomethyl ferulic acid lignin (H4) are generally rare

Method used

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  • Medical uses of methyl (E)-3-[2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-prop-2-enoate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 MTS method to determine the growth inhibitory effect of H4 on liver cancer cells

[0035] SK-HEP1 cells (purchased from the Cell Bank of the Chinese Academy of Sciences) were seeded into a 96-well plate at 3×103 / well, cultured for 24 hours to adhere to the wall, and then H4 (purchased from the Shanghai Institute of Materia Medica, Chinese Academy of Sciences) was added, with 6 concentration gradients. Set 3 multiple holes for each concentration. After the cells were cultured at 37°C and 5% CO2 for 72 hours, the culture medium was discarded, and the cell survival rate was measured with MTS kit (Promega).

[0036] The test method is: wash the cells once with serum-free medium, add the pre-prepared MTS coloring solution (add 2ml solution 1 and 100μl solution 2 to 10ml serum-free medium and mix well) according to the amount of 100μl / well. Set a hole without cells as the background hole to correct the background light absorption of the solution. Put the cells in the c...

Embodiment 2H4

[0040] Example 2H4's growth inhibitory effect on human leukemia cells

[0041] Use cck-8 kit (Japan Tongren Chemical Research Institute) to detect.

[0042] step:

[0043] 1) Plant K562 cells (purchased from the Cell Bank of the Chinese Academy of Sciences) evenly in a 96-well plate with 104 cells per well.

[0044] 2) After sticking to the wall, add medicine after overnight, add medicine (H4 concentration is 50, 16.67, 5.56, 1.85, 0.62μM), each concentration has 3 replicate holes.

[0045] 3) Cultivate for 48 hours, replace the complete medium with a mixture of serum-free medium and CCK8 (10:1), and incubate for 2 hours in an incubator at 37°C.

[0046] 4) Take 450nm as the measurement wavelength and 650nm as the control wavelength, and measure the reading on the microplate reader.

[0047] Results: The IC50 value of H4 on K562 cells was 1.59μM.

Embodiment 3H4

[0048] Example 3H4's growth inhibitory effect on human gastric cancer cells

[0049] Use cck-8 kit (Japan Tongren Chemical Research Institute) to detect.

[0050] step:

[0051] 1) Plant HGC cells (purchased from the Cell Bank of the Chinese Academy of Sciences) evenly in a 96-well plate, with 3500 cells per well.

[0052] 2) After sticking to the wall, add medicine after overnight, add medicine (H4 concentration is 50, 16.67, 5.56, 1.85, 0.62μM), each concentration has 3 replicate holes.

[0053] 3) Cultivate for 48 hours, replace the complete medium with a mixture of serum-free medium and CCK8 (10:1), and incubate for 2 hours in an incubator at 37°C.

[0054] 4) Take 450nm as the measurement wavelength and 650nm as the control wavelength, and measure the reading on the microplate reader.

[0055] Results: The IC50 value of H4 on HGC cells was 33.02μM.

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Abstract

The invention belongs to the fields of chemical industry and medicine, and relates to medical uses of methyl (E)-3-[2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-prop-2-enoate (hereafter referred to as H4 for short). The invention provides applications of H4 in preparation of antitumor drugs and a corresponding antitumor drug composition. The invention also provides a method for inhibiting tumor cell proliferation in vitro. According to the method, the H4 is added into nutrient solution of tumor cells, which include hepatoma cells, gastric cancer cells, or leukemia cells. The H4 is a natural product with small toxic side effects, high bioavailability and stable properties, and thus is valuable for clinical use. The small molecule provided by the invention is developed as a novel antitumor drug or an auxiliary component thereof, has a significant antitumor effect, and is environmentally friendly.

Description

Technical field [0001] The invention belongs to the field of chemical engineering and medicine, and relates to the use of 3-hydroxymethyldihydrobenzofuran dimerized monomethyl ferulic acid lignin in the preparation of antitumor drugs. Background technique [0002] 3-hydroxymethyldihydrobenzofuran dimer ferulic acid monomethyl lignin, the English name is methyl(E)-3-[2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7- methoxy-2,3-dihydro-1-ben zofuran-5-yl]-prop-2-enoate. In this application, it is referred to as H4 for short. Its structural formula is as follows: [0003] [0004] In 1986, Fukuyama et al. extracted a lignan lactone similar to H4 (A new neo-lignan, a prostaglandin I2 inducer from the leaves of Zizyphus jujuba., Planta Medica, (6), 501-2) from the leaves of jujube trees. ., 1986). [0005] Rakotondramanana et al. reported in detail the structure, characteristic parameters and preparation process of H4 (ie compound 5 in the text, Synthesis of ferulic ester dimers, func...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/343A61P35/00A61P35/02C12Q1/02
Inventor 余龙胡立宏刘祖龙刘军华王煜棋王正
Owner FUDAN UNIV
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