ArticleThe Journal of organic chemistry2011
A methodology for radiolabeling of the endocannabinoid 2-arachidonoylglycerol (2-AG).
Article in The Journal of organic chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed, 16 citations in OpenAlex.
- Preparation of 2-Arachidonoylglycerol by Enzymatic Alcoholysis: Effects of Solvent and Water Activity on Acyl Migration.Foods (Basel, Switzerland) · 2022Article
- 2-Arachidonoylglycerol Synthesis: Facile and Handy Enzymatic Method That Allows to Avoid Isomerization.Molecules (Basel, Switzerland) · 2022Article
- Article
- Synthesis of enantiopure reversed structured ether lipids of the 1-O-alkyl-sn-2,3-diacylglycerol type.Marine drugs · 2015Article
- Assay and inhibition of diacylglycerol lipase activity.Bioorganic & medicinal chemistry letters · 2012Article
- Article
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
Abstract
The metabolic intermediate and endocannabinoid signaling lipid 2-arachidonoylglycerol (2-AG) has not been readily labeled, primarily because of its instability toward rearrangement. We now detail a synthetic method that easily gives tritiated 2-AG from [5,6,8,9,11,12,14,15-(3)H(N)]arachidonic acid in two steps. We utilized a short chain 1,3-diacylglycerol and proceeded through the "structured lipid" [5'',6'',8'',9'',11'',12'',14'',15''-(3)H(N)]2-arachidonoyl-1,3-dibutyrylglycerol, a triacylglycerol that was conveniently deprotected in ethanol with acrylic beads containing Candida antarctica lipase B to give [5'',6'',8'',9'',11'',12'',14'',15''-(3)H(N)]2-arachidonoylglycerol ([(3)H]2-AG). The flash chromatographic separation necessary to isolate the labeled 2-acylglycerol [(3)H]2-AG resulted in only 4% of the rearrangement byproducts that have been a particular problem with previous methodologies. This reliable "kit" method to prepare the radiolabeled endocannabinoid as needed gave tritiated 2-arachidonoylglycerol [(3)H]2-AG with a specific activity of 200 Ci/mmol for enzyme assays, metabolic studies, and tissue imaging. It has been run on unlabeled materials on over 10 mg scales and should be generally applicable to other 2-acylglycerols.
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Registered trials
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