Discovery of a Highly Potent Anti-inflammatory Epoxyisoprostane-Derived Lactone

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 isoprostan...

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Published inJournal of the American Chemical Society Vol. 136; no. 50; pp. 17382 - 17385
Main Authors Egger, Julian, Bretscher, Peter, Freigang, Stefan, Kopf, Manfred, Carreira, Erick M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.12.2014
Amer Chemical Soc
Subjects
Anti-Inflammatory Agents - chemistry
Anti-Inflammatory Agents - metabolism
Chemistry
Chemistry, Multidisciplinary
Drug Discovery
Isoprostanes - chemistry
Isoprostanes - metabolism
Lactones - chemistry
Lactones - metabolism
Molecular Structure
Physical Sciences
Science & Technology
ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
BIOLOGICAL-ACTIVITIES
OXIDIZED PHOSPHOLIPIDS
CONJUGATE REDUCTION
PATHWAY
CYCLOPENTENONE PROSTAGLANDINS
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja509892u