10009962  2-(14,15-Epoxyeicosatrienoyl) Glycerol

2-14,15-EG (CAS 848667-56-1)



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• See more Endocannabinoids; Cancer; Cytochrome P450

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2-Arachidonoyl glycerol (2-AG) is an endogenous central cannabinoid (CB1) receptor agonist that is present at relatively high levels in the central nervous system.1,2,3 2-AG is hydrolyzed by the enzyme monoacylglycerol lipase, terminating its biological activity, and metabolism by cyclooxygenase-2 and lipoxygenases has been documented.4,5 The related endocannabinoid, 2-arachidonoyl ethanolamide (AEA), can be metabolized by cytochrome P450 (CYP450) enzymes in human liver and kidney to a number of epoxy-ethanolamide derivatives.6 2-14,15-EG is a novel CYP450 metabolite of 2-AG in the kidney.7 2-14,15-EG is a potent mitogen for renal epithelial cells, increasing DNA synthesis in LLCPKcl4 cells at concentrations as low as 100 nM and doubling cell proliferation rates at 1 µM.7 In these cells, 2-14,15-EG activates the metalloprotease ADAM17, which cleaves proTGF-α and releases TGF-α as a ligand that initiates the EGFR-ERK signalling pathway.
1  Stella, N., Schweitzer, P., Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388 773-778 (1997).
2  Sugiura, T., Kodaka, T., Nakane, S., et al. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. J Biol Chem 274 2794-2801 (1999).
3  Kondo, S., Kondo, H., Nakane, S., et al. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor agonist: Identification as one of the major species of monoacylglycerols in various rat tissues, and evidence for its generation through Ca2+-dependent and -independent mechanisms. FEBS Lett 429 152-156 (1998).
4  Dinh, T.P., Carpenter, D., Leslie, F.M., et al. Brain monoglyceride lipase participating in endocannabinoid inactivation. Proc Natl Acad Sci USA 99(16) 10819-10824 (2002).
5  Kozak, K.R., Marnett, L.J. Oxidative metabolism of endocannabinoids. Prostaglandins Leukot Essent Fatty Acids 66(2&3), 211-220 (2002).
6  Snider, N.T., Kornilov, A.M., Kent, U.M., et al. Anandamide metabolism by human liver and kidney microsomal cytochrome P450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides. J Pharmacol Exp Ther 321(2) 590-597 (2007).
7  Chen, J., Chen, J., Falck, J.R., et al. Mitogenic activity and signaling mechanism of 2-(14,15-epoxyeicosatrienoyl)glycerol, a novel cytochrome P450 arachidonate metabolite. Mol Cell Biol 27(8) 3023-3034 (2007).

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Pricing Information

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Size Price Quantity
25 µg €228.00
50 µg €434.00
100 µg €821.00
500 µg €3,192.00
Pricing updated 2010-08-01.
Prices are subject to change without notice.