110301-23-0Relevant articles and documents
Chemical tuning of photoswitchable azobenzenes: A photopharmacological case study using nicotinic transmission
Sansalone, Lorenzo,Zhao, Jun,Richers, Matthew T.,Ellis-Davies, Graham C.R.
, p. 2812 - 2821 (2019)
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 configu
Fluorinated Azobenzenes Switchable with Red Light
Leistner, Anna-Lena,Kirchner, Susanne,Karcher, Johannes,Bantle, Tobias,Schulte, Mariam L.,G?dtel, Peter,Fengler, Christian,Pianowski, Zbigniew L.
, p. 8094 - 8099 (2021)
Molecular photoswitches triggered with red or NIR light are optimal for photomodulation of complex biological systems, including efficient penetration of the human body for therapeutic purposes (“therapeutic window”). Yet, they are rarely reported, and ev
Red-shifted tetra-ortho-halo-azobenzenes for photo-regulated transmembrane anion transport
Bo, Zonghua,Duarte, Fernanda,Kerckhoffs, Aidan,Langton, Matthew J.,Penty, Samuel E.
supporting information, p. 9058 - 9067 (2021/11/04)
Photo-responsive synthetic ion transporters are of interest as tools for studying transmembrane transport processes and have potential applications as targeted therapeutics, due to the possibility of spatiotemporal control and wavelength-dependent function. Here we report the synthesis of novel symmetric and non-symmetric red-shifted tetra-ortho-chloro- and tetra-ortho-fluoro azobenzenes, bearing pendant amine functionality. Functionalisation of the photo-switchable scaffolds with squaramide hydrogen bond donors enabled the preparation of a family of anion receptors, which act as photo-regulated transmembrane chloride transporters in response to green or red light. The subtle effects of chlorine/fluorine substitution,meta/parapositioning of the anion receptors, and the use of more flexible linkers are explored. NMR titration experiments on the structurally diverse photo-switchable receptors reveal cooperative binding of chloride in theZ, but notEisomer, by the two squaramide binding sites. These results are supported by molecular dynamics simulations in explicit solvent and model membranes. We show that this intramolecular anion recognition leads to effective switching of transport activity in lipid bilayer membranes, in which optimalZisomer activity is achieved using a combination of fluorine substitution andpara-methylene spacer units.