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Synthesis of Resolvin E3, a Proresolving Lipid Mediator, and Its Deoxy Derivatives: Identification of 18-Deoxy-resolvin E3 as a Potent Anti-Inflammatory Agent

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journal contribution
posted on 2020-10-13, 15:38 authored by Hayato Fukuda, Hiroyuki Ikeda, Ryuta Muromoto, Koki Hirashima, Kohei Ishimura, Koichi Fujiwara, Haruka Aoki-Saito, Takeshi Hisada, Mizuki Watanabe, Jun Ishihara, Tadashi Matsuda, Satoshi Shuto
We synthesized RvE3 and its deoxy derivatives, 17-deoxy-RvE3 and 18-deoxy-RvE3, by a common route via Sonogashira coupling as a key step. The evaluation of their anti-inflammatory activities revealed that 18-deoxy-RvE3 was remarkably more potent than the parent RvE3 and significantly active at a 300 fg dose in mice; additionally, 17-deoxy-RvE3 was significantly less potent than the parent RvE3. For the first time, we found that the 17-hydroxy group of RvE3 is very important for anti-inflammatory activity.