| Identification | Back Directory | [Name]
19,20-EDP epoxide | [CAS]
2123485-34-5 | [Synonyms]
19,20-EDP epoxide
(±)19(20)-EDP Ethanolamide
4,7,10,13,16-Octadecapentaenamide, 18-(3-ethyl-2-oxiranyl)-N-(2-hydroxyethyl)-, (4Z,7Z,10Z,13Z,16Z)- | [Molecular Formula]
C24H37NO3 | [MOL File]
2123485-34-5.mol | [Molecular Weight]
387.56 |
| Hazard Information | Back Directory | [Description]
(±)19(20)-EDP ethanolamide is an ω-3 endocannabinoid epoxide and cannabinoid (CB) receptor agonist (EC50s = 108 and 280 nM for CB1 and CB2, respectively). It is produced through direct epoxygenation of docosahexaenoyl ethanolamide (DHEA; ) by cytochrome P450 (CYP) epoxygenases.1,2 (±)19(20)-EDP ethanolamide (25 μM) reduces the viability of 143B metastatic osteosarcoma cells.2 It decreases the production of IL-6 and increases the production of IL-10 when used at concentrations ranging from 2.5 to 10 μM in BV-2 microglia stimulated by LPS and decreases LPS-induced cytotoxicity when used at concentrations ranging from 5 to 10 μM. It also decreases nitrite production when used at a concentration of 7.5 μM, an effect that can be partially reversed by the CB2 receptor antagonist AM630 and the PPARγ antagonist GW 9662 . (±)19(20)-EDP ethanolamide induces vasodilation of isolated preconstricted bovine coronary arteries (ED50 = 1.9 μM) and reduces tube formation by human microvascular endothelial cells (HMVECs) in a Matrigel? assay. | [storage]
Store at -20°C | [References]
1. McDougle, D.R., Watson, J.E., Abdeen, A.A., et al. Anti-inflammatory ω-3 endocannabinoid epoxides Proc. Natl. Acad. Sci. USA 114(30),E6034-E6043(2017).
2. Roy, J., Watson, J.E., Hong, I.S., et al. Antitumorigenic properties of omega-3 endocannabinoid epoxides J. Med. Chem. 61(13),5569-5579(2018). |
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