Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling

Bioorg Med Chem Lett. 2008 Nov 15;18(22):5838-41. doi: 10.1016/j.bmcl.2008.06.091. Epub 2008 Jul 2.

Abstract

The endocannabinoid 2-arachidonoylglycerol (2-AG) has been implicated as a key retrograde mediator in the nervous system based on pharmacological studies using inhibitors of the 2-AG biosynthetic enzymes diacyglycerol lipase alpha and beta (DAGL-alpha/beta). Here, we show by competitive activity-based protein profiling that the DAGL-alpha/beta inhibitors, tetrahydrolipstatin (THL) and RHC80267, block several brain serine hydrolases with potencies equal to or greater than their inhibitory activity against DAGL enzymes. Interestingly, a minimal overlap in target profiles was observed for THL and RHC80267, suggesting that pharmacological effects observed with both agents may be viewed as good initial evidence for DAGL-dependent events.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arachidonic Acids / antagonists & inhibitors*
  • Arachidonic Acids / biosynthesis*
  • Brain / enzymology*
  • Cannabinoid Receptor Modulators / antagonists & inhibitors*
  • Cannabinoid Receptor Modulators / biosynthesis*
  • Cyclohexanones / pharmacology*
  • Endocannabinoids*
  • Glycerides / antagonists & inhibitors*
  • Glycerides / biosynthesis*
  • Humans
  • Isoenzymes / antagonists & inhibitors
  • Lactones / pharmacology*
  • Lipase / antagonists & inhibitors*
  • Molecular Structure
  • Orlistat
  • Receptor, Cannabinoid, CB1 / metabolism
  • Serine Proteinase Inhibitors / pharmacology*

Substances

  • Arachidonic Acids
  • Cannabinoid Receptor Modulators
  • Cyclohexanones
  • Endocannabinoids
  • Glycerides
  • Isoenzymes
  • Lactones
  • Receptor, Cannabinoid, CB1
  • Serine Proteinase Inhibitors
  • 1,6-bis(cyclohexyloximinocarbonyl)hexane
  • glyceryl 2-arachidonate
  • Orlistat
  • Lipase