1493763-10-2Relevant academic research and scientific papers
Optical control of acetylcholinesterase with a tacrine switch
Broichhagen, Johannes,Jurastow, Innokentij,Iwan, Katharina,Kummer, Wolfgang,Trauner, Dirk
, p. 7657 - 7660 (2014)
Photochromic ligands have been used to control a variety of biological functions, especially in neural systems. Recently, much effort has been invested in the photocontrol of ion channels and G-protein coupled receptors found in the synapse. Herein, we describe the expansion of our photopharmacological approach toward the remote control of an enzyme. Building on hallmark studies dating from the late 1960s, we evaluated photochromic inhibitors of one of the most important enzymes in synaptic transmission, acetylcholinesterase (AChE). Using structure-based design, we synthesized several azobenzene analogues of the well-known AChE inhibitor tacrine (THA) and determined their effects on enzymatic activity. One of our compounds, AzoTHA, is a reversible photochromic blocker of AChE in vitro and ex vivo with high affinity and fast kinetics. As such, AzoTHA can be used to control synaptic transmission on the neuromuscular endplate based on the light-dependent clearance of a neurotransmitter.
A simple and effective synthesis of aryl azides via arenediazonium tosylates
Kutonova, Ksenia V.,Trusova, Marina E.,Postnikov, Pavels.,Filimonov, Victor D.,Parello, Joseph
, p. 2706 - 2710 (2013/10/21)
Aromatic azides are formed in high yield from arenediazonium tosylates and sodium azide in water at room temperature or from aromatic amines via diazotization in the presence of p-TsOH Besides being experimentally simple, these methods do not require any metal catalysis and provide clean products without purification. Georg Thieme Verlag Stuttgart New York.
