Prostaglandin E2-1-glyceryl ester-d5

Prostaglandin E₂-1-glyceryl ester-d₅ (PGE₂-1-glyceryl ester-d₅) contains five deuterium atoms. It is intended for use as an internal standard for the quantification of PGE₂-1-glyceryl ester by GC- or LC-mass spectrometry. 2-Arachidonoyl glycerol (2-AG) has been isolated from porcine brain, and has been characterized as the natural endocannabinoid ligand for the central cannabinoid receptor.^1,2 Incubation of 2-AG with cyclooxygenase-2 and specific PGH₂ isomerases in cell cultures and isolated enzyme preparations results in PG glycerol ester formation.³ The biosynthesis of PGH, PGD, PGE, PGF, and thromboxane A-2-glyceryl ester compounds have all been documented. The 2-glyceryl ester moiety equilibrates rapidly (within minutes) with the more stable 1-glyceryl ester, producing a 10:90 2:1-glyceryl ester mixture in typical aqueous media. While the stability and metabolism of these prostaglandin products has been investigated, little is known about their intrinsic biological activity.⁴

1.Sugiura, T., Kodaka, T., Kondo, S., et al.2-Arachidonoylglycerol, a putative endogenous cannabinoid receptor ligand, induces rapid, transient elevation of intracellular free Ca2+ in neuroblastoma X glioma hybrid NG108-15 cellsBiochemical and Biophysical Research Communications22958-64(1996) 2.Sugiura, T., Kodaka, T., Kondo, S., et al.Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor• Structural requirements for triggering a Ca2+ transient in NG108-15 cellsJ. Biochem.122(4)890-895(1997) 3.Kozak, K.R., Crews, B.C., Morrow, J.D., et al.Metabolism of the endocannabinoids, 2-arachidonylgycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamidesJ. Biol. Chem.277(47)44877-44885(2002) 4.Kozak, K.R., Crews, B.C., Ray, J.L., et al.Metabolism of prostaglandin glycerol esters and prostaglandin ethanolamides in vitro and in vivoThe Journal of Biological Chemisty276(40)36993-36998(2001)