期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 135, 期 42, 页码 15948-15954出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja408225k
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资金
- NIH [GM053395, NS069720, MH085498]
- HFSP [RG0089/2009C]
- Helen Hay Whitney Foundation
- Charles A. King Trust
- Bank of America, Co-Trustee
- Howard Hughes Medical Institute
Caged compounds are molecules rendered functionally inert by derivatization with a photochemical protecting group. We describe the design logic behind the development of a diethylaminocoumarin (DEAC) caging chromophore, DEAC450, that absorbs blue light strongly (e450 = 43,000 M(-1) cm(-1)) and violet light 11-fold more weakly. The absorption minimum is in the wavelength range (340-360 nm) that is traditionally used for photolysis of many widely used nitroaromatic caged compounds (e.g., 4-carboxymethoxy-5,7-dinitroindolinyl(CDNI)-GABA). We used this chromophore to synthesize DEAC450-caged cAMP and found this probe was very stable toward aqueous hydrolysis in the electronic ground state but was photolyzed with a quantum efficiency of 0.78. When DEAC450-cAMP and CDNI-GABA where co-applied to striatal cholinergic interneurons, the caged compounds were photolyzed in an chromatically orthogonal manner using blue and violet light so as to modulate the neuronal firing rate in a bidirectional way.
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