@article{ScheinerSinkSpatzetal.2021,
  author    = {Scheiner, Matthias and Sink, Alexandra and Spatz, Philipp and Endres, Erik and Decker, Michael},
  title     = {Photopharmacology on Acetylcholinesterase: Novel Photoswitchable Inhibitors with Improved Pharmacological Profiles},
  series = {ChemPhotoChem},
  volume    = {5},
  journal   = {ChemPhotoChem},
  number    = {2},
  doi       = {10.1002/cptc.202000119},
  url       = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-218445},
  pages     = {149 -- 159},
  year      = {2021},
  abstract  = {Considerable effort has previously been invested in a light-controlled inhibition of the enzyme acetylcholinesterase (AChE). We found that a novel azobenzene-based bistacrine AChE inhibitor switched faster than the known dithienylethene based bistacrine and inverted the photo-controlled interactions of the photoisomers compared to its dithienylethene congener. Furthermore, we have optimized a previously described light-controlled tacrine-based AChE inhibitor. Isomerization upon irradiation with UV light of the novel inhibitor was observed in aqueous medium and showed no fatigue over several cycles. The cis-enriched form showed an 8.4-fold higher inhibition of hAChE compared with its trans-enriched form and was about 30-fold more active than the reference compound tacrine with a single-digit nanomolar inhibition. We went beyond proof-of-concept to discover photoswitchable AChE inhibitors with pharmacologically desirable nanomolar inhibition, "cis-on" effect, and pronounces differences between the photoisomers.},
  language  = {en}
}