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Discovery of a highly potent anti-inflammatory epoxyisoprostane-derived lactone.

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Author Egger Julian, Bretscher Peter, Freigang Stefan, Kopf Manfred, Carreira Eric,
Project An apparatus for the real-time analysis of cellular metabolism
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Original article (peer-reviewed)

Journal J Am Chem Soc
Volume (Issue) 136(50)
Page(s) 17382 - 17385
Title of proceedings J Am Chem Soc
DOI 10.1021/ja509892u


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.