Antiproliferative and apoptosis-inducing activities of alkyl gallate and gallamide derivatives related to (-)-epigallocatechin gallate

被引：47
作者：
Dodo, Kosuke [1 ,2 ]
Minato, Taro [1 ]
Noguchi-Yachide, Tomomi [1 ]
Suganuma, Masami [3 ]
Hashimoto, Yuichi [1 ]
机构：
[1] Univ Tokyo, Inst Mol & Cellular Biosci, Bunkyo Ku, Tokyo 1130032, Japan
[2] RIKEN, Wako, Saitama 3510198, Japan
[3] Saitama Canc Ctr, Res Inst Clin Oncol, Ina, Saitama 3620806, Japan
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2008年 / 16卷 / 17期
基金：
日本学术振兴会;
关键词：
gallate; gallamide; catechin; apoptosis; caspase;
D O I：
10.1016/j.bmc.2008.07.063
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Green tea and (-)-epigallocatechin gallate (EGCG: one of the main components of green tea) are reported to have cancer-preventive activity in humans. A previous SAR study of EGCG and derivatives indicated that a galloyl group is essential for the activity. To test this hypothesis, we synthesized various alkyl gallate and gallamide derivatives and evaluated their antiproliferative effects on human leukemia HL-60 cells. Dodecyl 3,4,5-trihydroxybenzoate (6c) showed the most potent activity, being more potent than EGCG. To clarify the molecular mechanism of the antiproliferative action, we investigated the effects of 6c on various factors. Compound 6c was found to induce apoptosis mediated by endoplasmic reticulum (ER)-stress-related caspase-12. Upregulation of gadd-153, an ER-stress marker protein, was also observed. These results indicate that 6c induced apoptosis via the ER-stress-related pathway. (C) 2008 Elsevier Ltd. All rights reserved.
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收藏
页码：7975 / 7982
页数：8
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