a-methylated derivatives of 2-arachidonyl glycerol: Synthesis, CB1 receptor activity and enzymatic stability

Research output: Scientific - peer-reviewArticle

Details

Original languageEnglish
Pages (from-to)2437-2440
JournalBioorganic & Medicinal chemistry letters
Issue number16
StatePublished - 2006
MoE publication typeA1 Journal article-refereed

Researchers

  • Teija Parkkari
  • Ari Koskinen

  • Mikko Myllymäki
  • Juha R. Savinainen
  • Susanna M. Saario
  • Joel A. Castillo-Melendez
  • Jarmo T. Laitinen
  • Tapio Nevalainen
  • Tomi Järvinen

Research units

Abstract

a-Methylated analogues of the endogenous cannabinoid, 2-arachidonoyl glycerol (2-AG), were synthesized aiming to the improved enzymatic stability of 2-AG. In addition, the CB1 activity properties of fluoro derivatives of 2-AG were studied. The CB1 receptor activity was determined by the [35S]GTPcS binding assay, and the enzymatic stability of a-methylated analogues was determined in rat cerebellar membranes. The results indicate that even if the a-methylated 2-AG derivatives are slightly weaker CB1 receptor agonists than 2-AG, they are clearly more stable than 2-AG. In addition, the results showed that the replacement of the hydroxyl group(s) of 2-AG by fluorine does not improve the CB1 activity of 2-AG.

    Research areas

  • 2 AG, cannabinoidi, CB1 reseptor, enzymatic stability, stereoselective synthesis

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