@article{cb97b6255de34bb38ebd90b7ebb3fbc4,
title = "Synthesis of Photoswitchable9-Tetrahydrocannabinol Derivatives Enables Optical Control of Cannabinoid Receptor 1 Signaling",
abstract = "The cannabinoid receptor 1 (CB1) is an inhibitory G protein-coupled receptor abundantly expressed in the central nervous system. It has rich pharmacology and largely accounts for the recreational use of cannabis. We describe efficient asymmetric syntheses of four photoswitchable 9-tetrahydrocannabinol derivatives (azo-THCs) from a central building block 3-Br-THC. Using electrophysiology and a FRET-based cAMP assay, two compounds are identified as potent CB1 agonists that change their effect upon illumination. As such, azo-THCs enable CB1-mediated optical control of inwardly rectifying potassium channels, as well as adenylyl cyclase.",
author = "Westphal, {Matthias V.} and Schafroth, {Michael A.} and Sarott, {Roman C.} and Imhof, {Michael A.} and Bold, {Christian P.} and Philipp Leippe and Amey Dhopeshwarkar and Grandner, {Jessica M.} and Vsevolod Katritch and Ken Mackie and Dirk Trauner and Carreira, {Erick M.} and Frank, {James A.}",
note = "Funding Information: E.M.C. gratefully acknowledges ETH Zurich and the Swiss National Science Foundation (200020_152898) for financial support. D.T., J.A.F., and P.L. gratefully acknowledge the Deutsche Forschungsgemeinschaft (TRR 152 project B19, SFB 1032 project B09) and the European Research Council (ERC Advanced Grant 268795 to D.T.) for financial support. K.M. gratefully acknowledges support from the U.S. National Institutes of Health (DA021696 and DA009158). We thank Simone Wouters for experimental assistance and Nicola{\'s} Armanino for helpful discussions. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",
year = "2017",
month = dec,
day = "20",
doi = "10.1021/jacs.7b06456",
language = "English (US)",
volume = "139",
pages = "18206--18212",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "50",
}