Prostaglandin D2 Ethanolamide-d4

Prostaglandin D₂ ethanolamide (PGD₂-EA)-d₄ contains four deuterium atoms. It is intended for use as an internal standard for the quantification of PGD₂-EA by GC- or LC-mass spectrometry. PGD₂-EA is a bioactive lipid produced by the sequential metabolism of anandamide (arachidonoyl ethanolamide) by cyclooxygenase (COX) enzymes, in particular by COX-2, and PGD synthase.^1,2,3 The biosynthesis of PGD₂-EA from anandamide can also be increased when anandamide metabolism is diminished by deletion of fatty acid amide hydrolase.⁴ PGD₂-EA is inactive against recombinant prostanoid receptors, including the D prostanoid receptor.⁵ It increases the frequency of miniature inhibitory postsynaptic currents in primary cultured hippocampal neurons, an effect which is the opposite of that induced by anandamide.³. PGD₂-EA also induces apoptosis in colorectal carcinoma cell lines.²

1.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) 2.Patsos, H.A., Hicks, D.J., Dobson, R.R.H., et al.The endogenous cannabinoid, anandamide, induces cell death in colorectal carcinoma cells: A possible role for cyclooxygenase 2Gut54(12)1741-1750(2005) 3.Sang, N., Zhang, J., and Chen, C.PGE2 glycerol ester, a COX-2 oxidative metabolite of 2-arachidonoyl glycerol, modulates inhibitory synaptic transmission in mouse hippocampal neuronsJ. Physiol.572(Pt 3)735-745(2006) 4.Weber, A., Ni, J., Ling, K.H.J., et al.Formation of prostamides from anandamide in FAAH knockout mice analyzed by HPLC with tandem mass spectrometryJ. Lipid. Res.45(4)757-763(2004) 5.Matias, I., Chen, J., De Petrocellis, L., et al.Prostaglandin ethanolamides (prostamides): In vitro pharmacology and metabolismJ. Pharmacol. Exp. Ther.309(2)745-757(2004)