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Application of quercetin derivative in preparation of antitumor medicine

A tumor drug and drug technology, applied in antitumor drugs, drug combinations, pharmaceutical formulations, etc., can solve the problems of poor solubility of quercetin, large intermolecular attraction, quercetin activity research and clinical application limitations, etc.

Inactive Publication Date: 2013-08-14
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003]However, because quercetin is a planar molecule, the molecular packing is relatively tight, the intermolecular attraction is strong, and it is not easily dispersed by solvent or solute, so the dissolution of quercetin Poor activity and low bioavailability (the peak plasma concentration is only 0.13~7.6 μmol / L), which greatly limits the activity research and clinical application of quercetin (Sun Tiemin, Sun Changshan, Dai Guangyuan, etc. Chinese medicine Journal of Chemistry, 2003,13(6):345~348; Bakhtiyor F. Rasulev, Nasrulla D. Abdullaev, Vladimir N. Syrov, et al. QSAR Comb. Sci.24,2005, 9:1056~1065.)

Method used

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  • Application of quercetin derivative in preparation of antitumor medicine
  • Application of quercetin derivative in preparation of antitumor medicine
  • Application of quercetin derivative in preparation of antitumor medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Example 1 Structural characterization of compound QB

[0015] M.p: 294.9~296.8 ℃;

[0016] 1 H NMR (400 MHz, DMSO) δ 12.43 (s, 1H,5-OH), 10.90 (s, 1H,7-OH), 10.59 (s, 1H,NH), 9.80 (s, 1H, 4′-OH ), 9.45 (s, 1H, 3′-OH), 7.95 (d, J = 8.8 Hz, 2H, 2′-H, 6′-H), 7.83 (d, J = 8.8 Hz, 2H,2×ph -H), 7.61 – 7.54 (m, 2H, 2×ph-H), 6.91 (d, J = 9.0 Hz, 1H, 5′-H), 6.46 (d, J = 2.0 Hz, 1H,8-H ), 6.24 (d, J = 2.0 Hz, 1H,6-H), 4.65 (s, 2H, COCH 2 ), 4.30 (q, J = 7.1 Hz, 2H,CH 3 CH 2 ), 1.32 (t, J = 7.1 Hz, 3H,CH 3 ).

[0017] 13 C NMR (101 MHz, DMSO) δ 178.04, 167.82, 165.77, 164.88, 161.57, 156.87, 156.30, 149.43, 145.81, 143.09, 137.19, 130.72, 125.16, 121.58, 120.93, 119.37, 116.26, 116.01, 104.43, 99.27, 94.24 , 71.67, 60.95, 14.68.

Embodiment 2

[0018] Example 2 Antitumor Activity Test

[0019] 2.1 Cell lines and reagents

[0020] Human esophageal squamous cell carcinoma cells EC109, human esophageal squamous cell carcinoma cells EC9706, human gastric cancer cells SGC7901 and mouse melanoma cells B16-F10 were purchased from the Cell Bank of Shanghai Institute of Biological Sciences, Chinese Academy of Sciences.

[0021] Dimethyl sulfoxide (DMSO), Sigma

[0022] Tetramethylazolazolium blue (MTT), Sigma

[0023] RPMI-1640 medium, Thermo Fisher Biochemicals (Beijing) Co., Ltd.

[0024] Fetal bovine serum, Thermo Fisher Biochemicals (Beijing) Co., Ltd.

[0025] Trypsin, Hangzhou Jinuo Biomedical Technology Co., Ltd.

[0026] Medium: Take RPMI-1640 medium, add 10% fetal bovine serum, penicillin 100U / mL, streptomycin 100μg / mL, mix well, store at 4°C for later use.

[0027] Cell cryopreservation solution: Add DMSO to the medium containing 10% fetal bovine serum to make the DMSO concentration 10%.

[0028] Trypsin d...

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Abstract

The invention discloses application of a compound (QB) shown in a formula I in preparation of medicines for prevention and / or treatment. The MTT experiment displays that the proliferation inhibition effects of the compound QB on the four tumor cells, such as human esophageal squamous carcinoma cell EC109, the human esophageal squamous carcinoma cell EC9706, the human gastric carcinoma cell SGC7901 and mouse melanoma cell B16-F10, are obviously superior to those of quercetin. The inhibition effect of (IC50=5.201mu g / mL) on the EC109 cells is equivalent to that of fluorouracil 5-FU(IC50=5.426mu g / mL), the toxic or side effect is relatively small, and the compound is a potential antitumor candidate compound.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to the application of quercetin derivatives in the preparation of antitumor drugs. Background technique [0002] Quercetin (quercetin, 3,3',4',5,7-pentahydroxyflavone) is one of the most abundant flavonoids in the plant kingdom, widely present in vegetables (onions, ginger, celery, etc.), fruits (apples, strawberries, etc.), Chinese herbal medicines (gingko, Panax notoginseng, Huai Mi, etc.) and many beverages (tea, coffee, red wine, and fruit juices). Quercetin has a variety of pharmacological activities, such as anti-oxidation, anti-tumor, anti-inflammation, vasodilation, etc. (Russo M, Spagnuolo C, Tedesco I, et al. Biochem Pharmacol., 2012 ,83(1):6-15; Bischoff SC. Curr Opin Clin Nutr Metab Care., 2008, 11(6):733-740.). Quercetin has chemoprevention and anti-cancer effects, and can exert anti-tumor effects by regulating the expression of tumor suppressor genes, b...

Claims

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Application Information

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IPC IPC(8): A61K31/352A61P35/00
Inventor 翟广玉颜子童渠文涛段艳丹
Owner ZHENGZHOU UNIV
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