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

Teija Parkkari, Ari M.P. Koskinen, Mikko Myllymäki, Juha R. Savinainen, Susanna M. Saario, Joel A. Castillo-Melendez, Jarmo T. Laitinen, Tapio Nevalainen, Tomi Järvinen

    Research output: Contribution to journalArticleScientificpeer-review

    5 Citations (Scopus)
    176 Downloads (Pure)

    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.
    Original languageEnglish
    Pages (from-to)2437-2440
    JournalBioorganic and Medicinal Chemistry Letters
    Issue number16
    DOIs
    Publication statusPublished - 2006
    MoE publication typeA1 Journal article-refereed

    Keywords

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

    Fingerprint

    Dive into the research topics of 'a-methylated derivatives of 2-arachidonyl glycerol: Synthesis, CB1 receptor activity and enzymatic stability'. Together they form a unique fingerprint.

    Cite this