28952-32-1Relevant articles and documents
Optical control of the nuclear bile acid receptor FXR with a photohormone
Morstein, Johannes,Trads, Julie B.,Hinnah, Konstantin,Willems, Sabine,Barber, David M.,Trauner, Michael,Merk, Daniel,Trauner, Dirk
, p. 429 - 434 (2020/01/21)
Herein, we report a photoswitchable modulator for a nuclear hormone receptor that exerts its hormonal effects in a light-dependent fashion. The azobenzene AzoGW enables optical control of the farnesoid X receptor (FXR), a key regulator of hepatic bile aci
Optimization of the azobenzene scaffold for reductive cleavage by dithionite; development of an azobenzene cleavable linker for proteomic applications
Leriche, Geoffray,Budin, Ghyslain,Brino, Laurent,Wagner, Alain
supporting information; experimental part, p. 4360 - 4364 (2010/09/20)
In this paper we conducted an extensive reactivity study to determine the key structural features that favour the dithionite-triggered reductive cleavage of the azo-arene group. Our stepwise investigation allowed identification of a highly reactive azo-arene structure 25 bearing a carboxylic acid, at the ortho position of the electron-poor arene and an ortho-Oalkyl-resorcinol as the electron-rich arene. Based on this 2(2′-alkoxy-4′-hydroxyphenylazo) benzoic acid (HAZA) scaffold, the orthogonally protected difunctional azo-arene cleavable linker 26 was designed and synthesized. Selective linker deprotection and derivatization was performed by introducing an alkyne reactive group and a biotin affinity tag. This optimized azo-arene cleavable linker led to a total cleavage in less than 10 s with only 1 mM dithionite. Similar results were obtained in biological media.
