Synthesis of piperlogs and analysis of their effects on cells

被引：23

作者：

Boskovic, Zarko V. ^{[1
,2
]}

Hussain, Mahmud M. ^{[1
,2
]}

Adams, Drew J. ^{[1
]}

Dai, Mingji ^{[1
,2
]}

Schreiber, Stuart L. ^{[1
,2
]}

机构：

[1] MIT, Howard Hughes Med Inst, Broad Inst, Cambridge, MA 02142 USA

[2] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

TETRAHEDRON | 2013年 / 69卷 / 36期

关键词：

Michael acceptors; Reactive oxygen species; Piperlongumine; Toxicity; S-GLUTATHIONYLATION; OXIDATIVE STRESS; MECHANISM;

D O I：

10.1016/j.tet.2013.05.080

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Piperlongumine (PL) is a naturally occurring small molecule previously shown to induce cell death preferentially in cancer cells relative to non-cancer cells. An initial effort to synthesize analogs highlighted the reactivities of both of piperlongumine's alpha,beta-unsaturated imide functionalities as key features determining PL's cellular effects. In this study, a second-generation of analogs was synthesized and evaluated in cells to gain further insight into how the reactivity, number, and orientation of PL's reactive olefins contribute to its ability to alter the physiology of cells. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：7559 / 7567

页数：9

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