Chemical synthesis and actions of 11,12-thiirano-hepoxilin A3 |
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| Institution: | 1. Division of Rheumatology, Inflammation and Immunity, Department of Medicine, Brigham and Women''s Hospital, Harvard Medical School, Boston, MA, USA;2. Division of Rheumatology, Cumming School of Medicine, University of Calgary, Calgary, Alberta, Canada;3. Division of Preventive Medicine, Department of Medicine, Brigham and Women''s Hospital, Harvard Medical School, Boston, MA, USA;4. Division of Cardiovascular Medicine, Brigham and Women''s Hospital and Harvard Medical School, Boston, MA, USA;5. Center for Lipid Metabolomics, Brigham and Women''s Hospital and Harvard Medical School, Boston, MA, USA;6. Systems Genetics and Genomics Unit, Channing Division of Network Medicine Brigham and Women''s Hospital and Harvard Medical School, Boston, Massachusetts, USA;1. DICMAPI, University of Naples Federico II, Napoli, Italy;2. Institute for Research on Combustion, Napoli, Italy |
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| Abstract: | A novel analog of hepoxilin A3 has been chemically synthesized in which the 11,12-epoxide group has been altered to a thiirano group. This has been accomplished through allylic rearrangement of unnatural (11R,12R)-hepoxilin B3 under Mitsunobu conditions, first into unnatural (11R,12R)-hepoxilin A3, followed by conversion of this compound with inversion of the epoxide centers into the thiirano-hepoxilin A3 having the natural 11S,12S configuration. We also report herein evidence showing that thiirano-hepoxilin A3 raises intracellular calcium concentrations in intact human neutrophils. |
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