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Bioorg Med Chem Lett. 2012 Aug 15;22(16):5322-5. doi: 10.1016/j.bmcl.2012.06.013. Epub 2012 Jun 15.

C3-heteroaroyl cannabinoids as photolabeling ligands for the CB2 cannabinoid receptor.

Author information

1
Department of Chemistry, University of Hawaii at Manoa, 2545 The Mall, Honolulu, HI 96822, USA.

Abstract

A series of tricyclic cannabinoids incorporating a heteroaroyl group at C3 were prepared as probes to explore the binding site(s) of the CB1 and CB2 receptors. This relatively unexplored structural motif is shown to be CB2 selective with K(i) values at low nanomolar concentrations when the heteroaromatic group is 3-benzothiophenyl (41) or 3-indolyl (50). When photoactivated, the lead compound 41 was shown to successfully label the CB2 receptor through covalent attachment at the active site while 50 failed to label. The benzothiophenone moiety may be a photoactivatable moiety suitable for selective labeling.

PMID:
22796181
PMCID:
PMC3445631
DOI:
10.1016/j.bmcl.2012.06.013
[Indexed for MEDLINE]
Free PMC Article

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