Coumarin-based octopamine phototriggers and their effects on an insect octopamine receptor.
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 important neurotransmitter.
Leibniz-Institut für Molekulare Pharmakologie (FMP), Robert-Rössle-Strasse 10, 13125 Berlin, Germany.
Janina
J
Schaal
Brigitte
B
Dekowski
Burkhard
B
Wiesner
Jenny
J
Eichhorst
Kathrin
K
Marter
Carolyn
C
Vargas
Sandro
S
Keller
Nadejda
N
Eremina
Andreas
A
Barth
Arnd
A
Baumann
Dorothea
D
Eisenhardt
Volker
V
Hagen
D000818:Animals; D001516:Bees / Q000378:metabolism; D020013:Calcium Signaling; D002245:Carbon Dioxide / Q000737:chemistry; D003374:Coumarins / Q000737:chemistry*; D057809:HEK293 Cells; D006801:Humans; D007259:Infrared Rays; D009655:Octopamine / Q000138:chemical synthesis / Q000737:chemistry*; D010782:Photolysis; D017982:Receptors, Biogenic Amine / Q000235:genetics / Q000378:metabolism*; D012995:Solubility; D014466:Ultraviolet Rays
D003374:Coumarins; D017982:Receptors, Biogenic Amine; C027604:norsynephrine receptor; D002245:Carbon Dioxide; D009655:Octopamine; C030123:coumarin