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

• Fukuda, Hayato

• Ikeda, Hiroyuki

• Muromoto, Ryuta

• Hirashima, Koki

• Ishimura, Kohei

• Fujiwara, Koichi

• Aoki-Saito, Haruka

• Hisada, Takeshi

• Watanabe, Mizuki

• Ishihara, Jun

• Matsuda, Tadashi

• Shuto, Satoshi

Abstract

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.

Journal

• Journal of organic chemistry

  Journal of organic chemistry 85 (21), 14190-14200, 2020-11-06

  American Chemical Society

Keywords

• Organic Chemistry

Details

• CRID: 1050290072638427520
• NII Article ID: 120007168587
• DOI: 10.1021/acs.joc.0c01701
• ISSN: 15206904
• ISSN: 00223263
• HANDLE: 2115/83204
• Web Site: https://pubs.acs.org/doi/pdf/10.1021/acs.joc.0c01701
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN