Details

Autor(en) / Beteiligte

• Arai, Shota
• Fujiwara, Koichi
• Kojima, Masahiro
• Aoki-Saito, Haruka
• Yatomi, Masakiyo
• Saito, Tsugumichi
• Koga, Yasuhiko
• Fukuda, Hayato
• Watanabe, Mizuki
• Matsunaga, Shigeki
• Hisada, Takeshi
• Shuto, Satoshi

Titel

Design and Synthesis of Cyclopropane Congeners of Resolvin E3, an Endogenous Pro-Resolving Lipid Mediator, as Its Stable Equivalents

Ist Teil von

• Journal of organic chemistry, 2022-08, Vol.87 (15), p.10501-10508

Ort / Verlag

American Chemical Society

Erscheinungsjahr

2022

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Resolvins are pro-resolving lipid mediators with highly potent anti-inflammatory effects. Because of their polyunsaturated structures, however, they are unstable to oxygen as a drug prototype. To address this issue, we designed and synthesized CP-RvE3 as oxidatively stable congeners of RvE3 by replacing the cis-olefin with a cis-cyclopropane to avoid the unstable bisallylic structure. Although the oxidative stabilities of CP-RvE3 were not improved, β-CP-RvE3 was 3.7 times more metabolically stable than RvE3. Thus, we identified β-CP-RvE3 as a metabolically stable equivalent.