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

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

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

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Title:	a-methylated derivatives of 2-arachidonyl glycerol: Synthesis, CB1 receptor activity and enzymatic stability
Author(s):	Parkkari, Teija ; Koskinen, Ari M.P. ; Myllymäki, Mikko ; Savinainen, Juha R. ; Saario, Susanna M. ; Castillo-Melendez, Joel A. ; Laitinen, Jarmo T. ; Nevalainen, Tapio ; Järvinen, Tomi
Date:	2006
Language:	en
Pages:	2437-2440
Department:	Department of Chemistry
Series:	Bioorganic & Medicinal chemistry letters, issue 16
DOI-number:	10.1016/j.bmcl.2006.01.101
Keywords:	2 AG, cannabinoidi, CB1 reseptor, enzymatic stability, stereoselective synthesis
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Citation: Parkkari , T , Koskinen , A M P , Myllymäki , M , Savinainen , J R , Saario , S M , Castillo-Melendez , J A , Laitinen , J T , Nevalainen , T & Järvinen , T 2006 , ' a-methylated derivatives of 2-arachidonyl glycerol: Synthesis, CB1 receptor activity and enzymatic stability ' , Bioorganic and Medicinal Chemistry Letters , no. 16 , pp. 2437-2440 . https://doi.org/10.1016/j.bmcl.2006.01.101
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.

Permanent link to this item: http://urn.fi/URN:NBN:fi:aalto-201609234333 Email this Export to RefWorks QR Code Print BibTex Tweet