title: Discovery of a highly potent anti-inflammatory epoxyisoprostane-derived lactone.
abstract: Epoxyisoprostanes EI (1) and EC (2) are effective inhibitors of the secretion of proinflammatory cytokines IL-6 and IL-12. In detailed studies toward the investigation of the molecular mode of action of these structures, a highly potent lactone (3) derived from 1 was identified. The known isoprostanoids 1 and 2 are most likely precursors of 3, the product of facile intramolecular reaction between the epoxide with the carboxylic acid in 2.
authors.affiliation: Laboratory of Organic Chemistry, ETH Zurich , HCI H335, Wolfgang-Pauli-Strasse 10, 8093 Zurich, Switzerland.
authors.forename: Julian
authors.initials: J
authors.lastname: Egger
authors.forename: Peter
authors.initials: P
authors.lastname: Bretscher
authors.forename: Stefan
authors.initials: S
authors.lastname: Freigang
authors.forename: Manfred
authors.initials: M
authors.lastname: Kopf
authors.forename: Erick M
authors.initials: EM
authors.lastname: Carreira
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000378:metabolism*; D055808:Drug Discovery; D028421:Isoprostanes / Q000737:chemistry / Q000378:metabolism*; D007783:Lactones / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure
chemical_list: D000893:Anti-Inflammatory Agents; D028421:Isoprostanes; D007783:Lactones; C000603551:epoxyisoprostane EC; C000603550:epoxyisoprostane EI