Download PDF
Synfacts 2021; 17(04): 0453
DOI: 10.1055/s-0040-1719461
Chemistry in Medicine and Biology

Optical Control of the Cannabinoid Receptor 2

Contributor(s):
Dirk Trauner
,
Johannes Morstein
Carreira EM, *, Frank A. * et al. Eidgenössische Technische Hochschule Zürich, Switzerland and Oregon Health & Science University, Portland, USA
Optical Control of Cannabinoid Receptor 2-Mediated Ca2+ Release Enabled by Synthesis of Photoswitchable Probes.

J. Am. Chem. Soc. 2021;
143: 736-743
DOI: 10.1021/jacs.0c08926.
CrossrefPubMedGoogle Scholar
› Further Information
 
 PDF Download Permissions and Reprints

Key words

G protein-coupled receptors - photoswitches - azobenzenes

Significance

Cannabinoid receptor 2 (CB2) is a G protein-coupled receptor with important roles in immunobiology. Pharmacological regulation holds promise for the treatment of neurological disorders. Photoswitchable probes would offer high spatiotemporal control, leading to new insights into CB2 signaling. The Carreira and Frank groups describe the development of azo-HU308-3, a probe that is inactive in the dark and can be activated upon irradiation with 375 nm light.


#

Comment

A series of three HU308-derived photoswitches (azo-HU308-1–3) were synthesized from the terpene (+)-verbenone. 3-OTf-HU308 could be accessed in seven robust and high-yielding steps. Azobenzene photoswitches were attached to this intermediate using Buchwald–Hartwig or Suzuki–Miyaura couplings with potassium trifluoroborate reagents C and D as pioneered by Molander (Synlett 2005, 1763).


#
#

Publication History

Article published online:
18 March 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany


   Permissions and Reprints