Design and Synthesis of Cyclopropane Congeners of Resolvin E2, an Endogenous Proresolving Lipid Mediator, as Its Stable Equivalents
Design and Synthesis of Cyclopropane Congeners of Resolvin E2, an Endogenous Proresolving Lipid Mediator, as Its Stable Equivalents
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DOI：
10.1021/acs.orglett.6b02612
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发表时间：
2016-12-16
期刊：
影响因子：
5.2
通讯作者：
Shuto, Satoshi
中科院分区：
文献类型：
--
作者：
Fukuda, Hayato;Muromoto, Ryuta;Shuto, Satoshi
具有高效抗炎活性的脂类化学介体解旋素可以开发新型抗炎药物，但由于其特有的多不饱和结构，它们在氧气中不稳定。为了解决这一问题，我们设计合成了Cp-RvE2，其中RvE2的顺式烯烃被环丙烷取代。Cp-RvE2抗自氧化能力比RvE2稳定得多，与RvE2相当或更强。Cp-RvE2被成功地鉴定为RvE2的稳定等价物。
Lipid chemical mediator resolvins with highly potent anti-inflammatory activity can be leads to develop novel anti-inflammatory drugs; however, they are unstable in oxygen due to their characteristic polyunsaturated structures. To solve the problem, CP-RvE2 has been designed and synthesized in which the cis-olefin of RvE2 was replaced with a cyclopropane. CP-RvE2s were much more stable than RvE2 against autoxidation and equipotent or more potent than RvE2. CP-RvE2s were successfully identified as stable equivalents of RvE2.