High affinity electrophilic and photoactivatable covalent endocannabinoid probes for the CB1 receptor

…, SK Vadivel, P Fan, A Makriyannis

Index: Li, Chen; Xu, Wei; Vadivel, Subramanian K.; Fan, Pusheng; Makriyannis, Alexandros Journal of Medicinal Chemistry, 2005 , vol. 48, # 20 p. 6423 - 6429

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Citation Number: 32

Abstract

We have designed and synthesized the first two high affinity covalent anandamide probes for the CB1 receptor by introducing either an electrophilic isothiocyanato or a photoactivatable azido group at the terminal carbon of the arachidonic acid moiety. The headgroup of these anandamide analogues was optimized by using a cyclopropylamide substituent to impart optimal CB1 affinity. Both 20-isothiocyanato-eicosa-5, 8, 11, 14- ...