19(20)-edp ethanolamide

(±)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 by cytochrome P450 (CYP) epoxygenases. (±)19(20)-EDP ethanolamide (25 μM) reduces the viability of 143B metastatic osteosarcoma cells. 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.

(±)10(11)-EDP ethanolamide is an ω-3 endocannabinoid epoxide and cannabinoid (CB) receptor agonist (EC50s = 0.43 and 22.5 nM for CB1 and CB2 receptors, respectively). It is produced though direct epoxygenation of docosahexaenoyl ethanolamide by cytochrome P450 (CYP) epoxygenases. 10,11-EDP epoxide (12.5 and 25 μM) reduces the viability of 143B metastatic osteosarcoma cells. It induces apoptosis and inhibits cell migration in a wound-healing assay in 143B, MG63, and HOS osteosarcoma cells. (±)10(11)-EDP ethanolamide also reduces tube formation by human umbilical vein endothelial cells (HUVECs) in a Matrigel assay.