Uses
Arachidonoyl Serinol, an endogenous cannabimimetic metabolite, is an inhibitor of monoacylglycerol lipase (MAGL). Arachidonoyl Serinol inhibits the hydrolysis of [3H]2-oleoylglycerol and [3H]anandamide with IC50s of ～70 μM[1][2][3].
Definition
ChEBI: N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-(1,3-dihydroxy-propyl-2-amine) is a fatty amide.
Biological Activity
arachidonoyl serinol is an amide bond-containing analogue of 2-arachidonoylglycerol, exhibited only weak cb1 receptor agonistic activity. 2-arachidonoyl glycerol (2-ag), a product of increased inositol phospholipid metabolism, is the natural endocannabinoid ligand for the cb1 receptor [1][2][3].cannabinoid receptor (cb1) was first identified in rat brain in 1988. n-arachidonoylethanolamine (anandamide) binds to the cannabinoid receptor and exhibits various cannabimimetic activities. anandamide inhibits calcium currents in n18 neuroblastoma cells, inhibits forskolin-stimulated adenylase cyclase activity, electrically evokes twitch response of the mouse vas deferens, and causes analgesia, hypothermia, hypoactivity, and catalepsy [3]. anandamide acts as a weak agonist and 2-arachidonoylglycerol may be an endogenous cannabinoid receptor agonist in nervous tissues [1].replacement of the sn-2 oxygen in the glycerol moiety of 2-ag with a nitrogen atom produces arachidonoyl serinol. in ng108-15 cells, arachidonoyl serinol induced a weak elevation of [ca2+]i [1][2].
References
[1] Khanolkar AD, et, al. Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand. J Med Chem. 1996 Oct 25;39(22):4515-9. DOI:
10.1021/jm960152y[2] Fowler CJ, et, al. Cyclooxygenation of the arachidonoyl side chain of 1-arachidonoylglycerol and related compounds block their ability to prevent anandamide and 2-oleoylglycerol metabolism by rat brain in vitro. Biochem Pharmacol. 2005 Apr 15;69(8):1241-5. DOI:
10.1016/j.bcp.2005.01.016[3] Ghafouri N, et, al. Inhibition of monoacylglycerol lipase and fatty acid amide hydrolase by analogues of 2-arachidonoylglycerol. Br J Pharmacol. 2004 Nov;143(6):774-84. DOI:
10.1038/sj.bjp.0705948
