Curcumin salicylic acid monoester and synthesis method thereof and application curcumin salicylic acid monoester to anti-tumor and anti-inflammatory aspects

A technology of curcumin salicyloyl monoester and curcumin, which is applied in the field of pharmacy, can solve problems such as unstable properties, difficulty in reaching effective concentrations, and restrictions on the use range of curcumin, and achieve excellent anti-tumor effects

Active Publication Date: 2012-08-29
FUJIAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, its properties are unstable, its metabolism is rapid in the body, its bioavailability is low, and it is difficult to reach an effective concentration in the body, which restricts the use of curcumin in the field of anticancer drugs.

Method used

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  • Curcumin salicylic acid monoester and synthesis method thereof and application curcumin salicylic acid monoester to anti-tumor and anti-inflammatory aspects
  • Curcumin salicylic acid monoester and synthesis method thereof and application curcumin salicylic acid monoester to anti-tumor and anti-inflammatory aspects
  • Curcumin salicylic acid monoester and synthesis method thereof and application curcumin salicylic acid monoester to anti-tumor and anti-inflammatory aspects

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The synthesis of embodiment 1 curcumin salicyloyl monoester

[0028] Under ice bath, 10 mmol (3.68 g) of curcumin was dissolved in 80 mL of anhydrous dichloromethane, and 7.5 mmol (1.035 g) of salicylic acid and catalyst DMAP (0.5 g) were added. Slowly add 10 ml of anhydrous dichloromethane dissolved with 2.22 g of DCC dropwise, continue to stir and react for 24 hours, reclaim the solvent to obtain a solid product, the product is dissolved in ethyl acetate, and purified by silica gel column chromatography, eluent toluene: acetic acid Ethyl ester=14:1, to obtain the pure product of yellow curcumin salicyloyl monoester.

[0029] Molecular formula C 28 h 24 o 8 , melting point 166°C, yellow crystal, 1 H NMR (D6-DMSO): 3.85(s, 6H, 2Ar-OCH 3 ), 6.15(s, 1H), 6.80(d, 2H, J=16Hz, -C H =CH-Ar), 6.83-7.19(m, 3H, Ar), 7.33(d, 1H, J=8Hz,), 7.38-7.61(m, 5H, Ar), 7.64(d, 2H, J=16Hz, -C H =CH-Ar) 8.01 (d, 1H, Ar), 9.69 (s, 1H, Ar-OH), 10.24 (s, 1H, Ar-OH), 13 C NMR(D6-DMSO):5...

Embodiment 2

[0030] The verification of the in vitro antitumor activity of embodiment 2 curcumin salicyloyl monoester

[0031] 2.1 Material description

[0032] Tumor cell lines: human chronic myelogenous leukemia cell line K562; human acute leukemia cell line HL60; human multiple myeloma cell line U266; Burkitts lymphoma cell line CA46; human gastric cancer cell line SGC7901; human colon cancer cell line SW1116; Liver cancer cell line SMMC7721; human pancreatic cancer cell line PANC-1; human cervical cancer cell line Hela; human breast cancer cell line MCF-7; human nasopharyngeal carcinoma CNE2; human nasopharyngeal carcinoma CNE1; mouse melanoma cell line B16, The above cells were all obtained from the Shanghai Cell Bank of the Chinese Academy of Sciences.

[0033] 2.2 Experimental method

[0034] Tumor cells were cultured in RPMI 1640 medium containing 10% calf serum, 100 IU / ml penicillin and 100 μg / ml streptomycin in an incubator at 37°C with 5% CO2 saturated humidity. Cells in the ...

Embodiment 3

[0040] The effect of embodiment 3 curcumin salicyloyl monoester on mouse liver cancer H22 xenograft model

[0041] 3.1 Materials 8-12 weeks old Kunming healthy mice, weighing (20±2) g; the mice were provided by the Experimental Animal Center of Fujian Medical University. Mouse hepatoma cell line H22.

[0042] 3.2 Method

[0043] 3.2.1 Establishment of tumor-bearing mouse model

[0044] H22 tumor cells were passed on for more than two generations, and the number of cells was adjusted to 10 7 / ml, 0.2mL / only inoculated in the abdominal cavity of mice, inoculated 6 mice, waited for about two weeks, aseptically extracted ascites, added sterile normal saline to adjust the number of cells, and then inoculated (each inoculated cells were about 2×10 6 ).

[0045] 3.2.2 Grouping

[0046] Be divided into 5 groups altogether: the mouse after inoculating tumor strain 24h is divided into 5 groups at random: normal saline control group, curcumin salicyl monoester (following examples sa...

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Abstract

The invention relates to curcumin salicylic acid monoester shown as a formula (I). A synthesis method of the curcumin salicylic acid monoester comprises the following steps of: dissolving curcumin in absolute methylene dichloride; adding salicylic acid and a catalytic amount of DMAP (N, N-4-dimethyl aminopyridine); slowly dropwise adding methylene dichloride in which a dehydrant DCC (dicyclohexylcarbodiimide) or EDC.HCl [1-ethyl-(3-dimethyl amino propyl) carbonyl diimine hydrochloride] to perform esterification reaction; and performing separation and purification on a product through column chromatography. The curcumin salicylic acid monoester has an inhibition effect on leukemia, lymphoma, gastric cancer, cancer of colon, liver cancer, pancreatic cancer, breast carcinoma, nasopharyngeal carcinoma, cervical cancer, melanoma and multiple myeloma cells; the anti-tumor effect is superior to that of curcumin; and the toxicity of a medicament is not increased while the anti-tumor effect is improved. The curcumin salicylic acid monoester has an obvious inhibition effect on acute and chronic inflammation models.

Description

technical field [0001] The invention relates to curcumin salicyloyl monoester and its synthesis method, as well as its application in anti-tumor and anti-inflammation aspects, and belongs to the field of pharmacy. Background technique [0002] Curcumin, the English name is Curcumin (abbreviated as Cur), and the molecular formula is C 21 h 20 o 6 , IUPAC named (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, the chemical formula is as follows: [0003] [0004] Curcumin is an active ingredient extracted from the rhizomes of turmeric, zedoary, turmeric, etc. of the genus Curcuma in the family Zingiberaceae. It is an orange-yellow crystalline powder, insoluble in water and ether, soluble in ethanol, acetone, glacial acetic acid and propylene glycol, and in acid It is light yellow under certain conditions, and turns yellow-red when dissolved in concentrated sulfuric acid. It can form chelates with metal ions and change color. Curcumin has various pharm...

Claims

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Application Information

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IPC IPC(8): C07C69/88C07C67/08A61K31/618A61P35/00A61P35/02A61P29/00
Inventor 许建华叶丽香刘洋王晓露叶敏叶胜难吴文伟
Owner FUJIAN MEDICAL UNIV
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