Optical control of the nuclear bile acid receptor FXR with a photohormone
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
Optically active and photoswitchable Tr?ger's base analogs
The enantiomer separation of a chiral Tr?ger's base analog and its use, as an optically active building block, in the construction of molecular superstructures are presented. Various strategies are illustrated here for the attachment of azo photoswitches to the Tr?ger's base scaffold without racemizing its stereogenic centers. The resulting optically active photoswitches introduced chirality, thermochromic, and phototunable properties to an achiral liquid crystal host. The doped mesophases reflected specific wavelengths of light owing to the formation of self-organized helical superstructures. These observations illustrate the potential use of the presented products as liquid crystal dopants.
Kazem-Rostami, Masoud
supporting information
p. 7751 - 7755
(2019/05/27)
Optimization of the azobenzene scaffold for reductive cleavage by dithionite; development of an azobenzene cleavable linker for proteomic applications
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.
Influence of helical twisting power on the photoswitching behavior of chiral azobenzene compounds: Applications to high-performance switching devices
Five photochromic chiral azobenzene compounds and one nonphotochromic chiral compound were synthesized and characterized by IR, 1H NMR spectroscopy, and elemental analysis. Cholesteric liquid crystalline phases were induced by mixing of the non