Photochromic Dopamine Receptor Ligands Based on Dithienylethenes and Fulgides
Lachmann D, Studte C, Männel B, Hübner H, Gmeiner P, Koenig B (2017)
Publication Status: Published
Publication Type: Journal article, Original article
Publication year: 2017
Journal
Publisher: WILEY-V C H VERLAG GMBH
Book Volume: 23
Pages Range: 13423-13434
Journal Issue: 54
Abstract
We describe the incorporation of the well-investigated class of photochromic dithienylethenes (DTEs) and fulgides into known dopamine receptor ligands such as 1,4-disubstituted aromatic and hydroxybenzoxazinone piperazines as well as aminoindanes. Subtype and functional selective photochromic ligands were obtained and characterized by NMR and UV/VIS spectroscopic measurements. The photophysical properties of the DTE based dopamine ligands revealed a high fatigue resistance for the diarylmaleimides, but the ringclosure could not be accomplished in polar solvents due to a known twisted intramolecular charge transfer (TICT). Several cyclopentene-DTEs showed high PSS, but a fast degradation by forming an irreversible byproduct. Focusing on the fulgides, high photostationary states and switching in polar solvents were possible. The compounds 43, 45 and 46 containing the isopropyl group showed only isomerization between the open E-form and the closed C-form. At a concentration of 1 nm, the cyclopentene-DTE 29-open showed a more than 11-fold higher activation of D-2S, a pharmacologically important G protein-coupled receptor, than its photochromic congener 29-closed. Interestingly, the fulgimide-based pair 52-(E)-open/52-closed could be discovered as an alternative photoswitch with inverse activation properties exhibiting four-fold higher activity in the closed state.
Authors with CRIS profile
Barbara Männel
Graduiertenkolleg 1910/3 Medizinische Chemie selektiver GPCR-Liganden
Harald Hübner
Lehrstuhl für Pharmazeutische Chemie
Peter Gmeiner
Lehrstuhl für Pharmazeutische Chemie
Additional Organisation(s)
Involved external institutions
Germany (DE)How to cite
APA:
Lachmann, D., Studte, C., Männel, B., Hübner, H., Gmeiner, P., & Koenig, B. (2017). Photochromic Dopamine Receptor Ligands Based on Dithienylethenes and Fulgides. Chemistry - A European Journal, 23(54), 13423-13434. https://doi.org/10.1002/chem.201702147
MLA:
Lachmann, Daniel, et al. "Photochromic Dopamine Receptor Ligands Based on Dithienylethenes and Fulgides." Chemistry - A European Journal 23.54 (2017): 13423-13434.
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