Design and Synthesis of Cyclopropane Congeners of
Resolvin E2, an Endogenous Proresolving Lipid Mediator, as Its Stable
Equivalents

Fukuda, Hayato; Muromoto, Ryuta; Takakura, Yuuki; Ishimura, Kohei; Kanada, Ryutaro; Fushihara, Daichi; Tanabe, Makoto; Matsubara, Kotaro; Hirao, Toru; Hirashima, Koki; Abe, Hiroshi; Arisawa, Mitsuhiro; Matsuda, Tadashi; Shuto, Satoshi

doi:10.1021/acs.orglett.6b02612.s001

ol6b02612_si_001.pdf (8.14 MB)

Design and Synthesis of Cyclopropane Congeners of Resolvin E2, an Endogenous Proresolving Lipid Mediator, as Its Stable Equivalents

journal contribution

posted on 28.11.2016, 16:51 by Hayato Fukuda, Ryuta Muromoto, Yuuki Takakura, Kohei Ishimura, Ryutaro Kanada, Daichi Fushihara, Makoto Tanabe, Kotaro Matsubara, Toru Hirao, Koki Hirashima, Hiroshi Abe, Mitsuhiro Arisawa, Tadashi Matsuda, Satoshi Shuto

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.