250684-63-0Relevant academic research and scientific papers
Activation of Sirtuin 2 Inhibitors Employing Photoswitchable Geometry and Aqueous Solubility
Grathwol, Christoph W.,W?ssner, Nathalie,Behnisch-Cornwell, Steven,Schulig, Lukas,Zhang, Lin,Einsle, Oliver,Jung, Manfred,Link, Andreas
supporting information, p. 1480 - 1489 (2020/05/25)
Because isoenzymes of the experimentally and therapeutically extremely relevant sirtuin family show high similarity, addressing the unique selectivity pocket of sirtuin 2 is a promising strategy towards selective inhibitors. An unrelated approach towards selective inhibition of isoenzymes with varied tissue distribution is targeted drug delivery or spatiotemporal activation by photochemical activation. Azologization of two nicotinamide-mimicking lead structures was undertaken to combine both approaches and yielded a set of 33 azobenzenes and azopyridines that have been evaluated for their photochemical behaviour and bioactivity. For some compounds, inhibitory activity reached the sub-micromolar range in their thermodynamically favoured E form and could be decreased by photoisomerization to the metastable Z form. Besides, derivatization with long-chain fatty acids yielded potent sirtuin 2 inhibitors, featuring another intriguing aspect of azo-based photoswitches. In these compounds, switching to the Z isomer increased aqueous solubility and thereby enhanced biological activity by up to a factor of 21. The biological activity of two compounds was confirmed by hyperacetylation of sirtuin specific histone proteins in a cell-based activity assay.
A New Class of Rigid Multi(azobenzene) Switches Featuring Electronic Decoupling: Unravelling the Isomerization in Individual Photochromes
Galanti, Agostino,Santoro, Jasmin,Mannancherry, Rajesh,Duez, Quentin,Diez-Cabanes, Valentin,Valá?ek, Michal,De Winter, Julien,Cornil, Jér?me,Gerbaux, Pascal,Mayor, Marcel,Samorì, Paolo
supporting information, p. 9273 - 9283 (2019/06/07)
We report a novel class of star-shaped multiazobenzene photoswitches comprising individual photochromes connected to a central trisubstituted 1,3,5-benzene core. The unique design of such C3-symmetric molecules, consisting of conformationally r
Electronic Decoupling in C3-Symmetrical Light-Responsive Tris(Azobenzene) Scaffolds: Self-Assembly and Multiphotochromism
Galanti, Agostino,Diez-Cabanes, Valentin,Santoro, Jasmin,Valá?ek, Michal,Minoia, Andrea,Mayor, Marcel,Cornil, Jér?me,Samorì, Paolo
supporting information, p. 16062 - 16070 (2018/11/23)
We report the synthesis of a novel C3-symmetrical multiphotochromic molecule bearing three azobenzene units at positions 1, 3, 5 of the central phenyl ring. The unique geometrical design of such a rigid scaffold enables the electronic decouplin
α,α-difluorophosphonomethyl azobenzene derivatives as photoregulated phosphoamino acid analogs. 1. Design and synthesis
Park, Seung Bum,Standaert, Robert F.
, p. 6557 - 6560 (2007/10/03)
A series of novel, photoregulated phosphoamino acid analogs based on an azobenzene core bearing an α,α-difluoromethylphosphonate as a hydrolytically stable phosphate isostere have been prepared with N-Fmoc protection for use in peptide synthesis. Classes of reagents analogous to both phosphotyrosine and phosphoserine/threonine were prepared by a common route employing a nitrosoarene/aniline condensation to form the azo linkage and the Cu(I)-promoted coupling of an iodoarene with (diethylphosphono)difluoromethyl cadmium bromide (Burton's method) to introduce the phosphonate moiety.
