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

Egger, Julian; Bretscher, Peter; Freigang, Stefan Bernd; Kopf, Manfred; Carreira, Erick M (2014). Discovery of a highly potent anti-inflammatory epoxyisoprostane-derived lactone. Journal of the American Chemical Society, 136(50), pp. 17382-17385. American Chemical Society 10.1021/ja509892u

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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.

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