Synthesis of New 7-O-Modified Chrysin Derivatives and Their Anti-proliferative and Apoptotic Effects on Human Gastric Carcinoma MGC-803 Cells

doi:10.1007/s40242-014-4269-6

Chemical Research in Chinese Universities ›› 2014, Vol. 30 ›› Issue (6): 925-930.doi: 10.1007/s40242-014-4269-6

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Synthesis of New 7-O-Modified Chrysin Derivatives and Their Anti-proliferative and Apoptotic Effects on Human Gastric Carcinoma MGC-803 Cells

LIU Yunmei¹, SONG Xiudao^1,2, MA Jin³, HE Jun⁴, ZHENG Xing¹, LEI Xiaoyong¹, JIANG Guorong², ZHAO Zihao¹, PAN Xia¹

1. Institute of Pharmacy & Pharmacology, University of South China, Hengyang 421001, P. R. China;
2. Suzhou Academy of Wumen Chinese Medicine, Suzhou Hospital of Traditional Chinese Medicine, Suzhou 215003, P. R. China;
3. Soochow University Affiliated Children's Hospital, Suzhou 215003, P. R. China;
4. Institute of Chemistry & Chemical Engineering, University of South China, Hengyang 421001, P. R. China

Received:2014-07-18 Revised:2014-09-04 Online:2014-12-01 Published:2014-09-22
Contact: LIU Yunmei E-mail:lymhsm2013@126.com
Supported by:
Supported by the Construct Program of the Key Discipline in Hunan Province, China(No.[2011]76).

Abstract

Abstract:

Two series of 7-O-modified chrysin derivatives were prepared from 7-O-carboxymethyl chrysin(2a), 7-O-carboxypropylchrysin(2b) and short-chain alcohols by using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride(EDCI), N-hydroxybenzotriazole(HOBt) and 4-dimethylamiopryidine(DMAP) as coupling reagents. Taking cisplatin as a reference substance, their anti-proliferative activities in vitro against human gastric carcinoma MGC-803 cells were evaluated by the standard 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) method. The results show that among the compounds tested, hepty 4-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy) acetate(3f) displayed the most potent growth-inhibitory effect on MGC-803 cells with half maximal inhibitory concentration(IC₅₀) value of 3.23 μmol/L. The preliminary mechanism of inhibitory effect of compound 3f was also detected by flow cytometry(FCM), and the compound exerted anti- cancer activity via inducing the apoptosis of MGC-803 cells in a dose dependent manner, which suggested that compound 3f would be a potential anti-cancer agent.

Key words: 7-O-Modified chrysin, Anti-proliferative effect, Apoptotic effect, Flavanoid

LIU Yunmei, SONG Xiudao, MA Jin, HE Jun, ZHENG Xing, LEI Xiaoyong, JIANG Guorong, ZHAO Zihao, PAN Xia. Synthesis of New 7-O-Modified Chrysin Derivatives and Their Anti-proliferative and Apoptotic Effects on Human Gastric Carcinoma MGC-803 Cells[J]. Chemical Research in Chinese Universities, 2014, 30(6): 925-930.

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Synthesis of New 7-O-Modified Chrysin Derivatives and Their Anti-proliferative and Apoptotic Effects on Human Gastric Carcinoma MGC-803 Cells

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