Coumarin-Based Octopamine Phototriggers and their Effects on an Insect Octopamine Receptor

被引：7
|
作者：
Schaal, Janina [1 ,2 ]
Dekowski, Brigitte [2 ]
Wiesner, Burkhard [2 ]
Eichhorst, Jenny [2 ]
Marter, Kathrin [1 ]
Vargas, Carolyn [3 ]
Keller, Sandro [3 ]
Eremina, Nadejda [4 ]
Barth, Andreas [4 ]
Baumann, Arnd [5 ]
Eisenhardt, Dorothea [1 ]
Hagen, Volker [2 ]
机构：
[1] Free Univ Berlin, Inst Biol, D-14195 Berlin, Germany
[2] Leibniz Inst Mol Pharmakol FMP, D-13125 Berlin, Germany
[3] Univ Kaiserslautern, D-67663 Kaiserslautern, Germany
[4] Stockholm Univ, Dept Biochem & Biophys, S-10691 Stockholm, Sweden
[5] Forschungszentrum Julich, Inst Complex Syst, D-52425 Julich, Germany
来源：
CHEMBIOCHEM | 2012年 / 13卷 / 10期
关键词：
caged compounds; coumarins; neurotransmitters; photolysis; protecting groups; FUNCTIONAL-CHARACTERIZATION; PROTECTING GROUPS; PHOTOCLEAVAGE; BEHAVIOR; RELEASE;
D O I：
10.1002/cbic.201200110
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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 (AmOcta1R). Upon irradiation with UVvisible or IR light, bioactive octopamine was released and evoked Ca2+ signals in AmOcta1R-expressing cells. The pronounced water solubility of compounds 24 in particular holds great promise for these substances as excellent phototriggers of this important neurotransmitter.
引用
收藏
页码：1458 / 1464
页数：7
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