Coumarin-based octopamine phototriggers and their effects on an insect octopamine receptor
- Schaal, J.
- Dekowski, B.
- Eisenhardt, D.
- Hagen, V.
- Wiesner, B.
- Eichhorst, J.
- Marter, K.
- Vargas, C.
- Keller, S.
- Eremina, N.
- Barth, A.
- Baumann, A.
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DOIAbstract
We have developed and characterized efficient caged compounds of the neurotransmitter octopamine. For derivatization, we introduced [6-bromo-8-(diethylaminomethyl)-7-hydroxycoumarin-4-yl]methoxycarbonyl (DBHCMOC) and {6-bromo-7-hydroxy-8-[(piperazin-1-yl)methyl]coumarin-4-yl}methoxycarbonyl (PBHCMOC) moieties as novel photo-removable protecting groups. The caged compounds were functionally inactive when applied to heterologously expressed octopamine receptors (AmOctα1R). Upon irradiation with UV-visible or IR light, bioactive octopamine was released and evoked Ca2+ signals in AmOctα1R-expressing cells. The pronounced water solubility of compounds 2-4 in particular holds great promise for these substances as excellent phototriggers of this i...