Chemical tuning of photoswitchable azobenzenes: a photopharmacological case study using nicotinic transmission.

ABSTRACT: We have developed photochromic probes for the nicotinic acetylcholine receptor that exploit the unique chemical properties of the tetrafluoroazobenzene (4FAB) scaffold. Ultraviolet light switching and rapid thermal relaxation of the metastable cis configuration are the main drawbacks associated with standard AB-based switches. We designed our photoprobes to take advantage of the excellent thermodynamic stability of the cis-4FAB configuration (thermal half-life > 12 days at 37 °C in physiological buffer) and cis-trans photostationary states above 84%. Furthermore, the well-separated n-π* absorption bands of trans- and cis-4FAB allow facile photoswitching with visible light in two optical channels. A convergent 11-step synthetic approach allowed the install

SUBMITTER: Sansalone L 

PROVIDER: S-EPMC6880823 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature