biostudies-literatureOlson JPNIDA NIH HHSHoward Hughes Medical InstituteNIMH NIH HHSNINDS NIH HHSNIGMS NIH HHS15948-54https://www.ebi.ac.uk/biostudies/studies/S-EPMC4097017biostudies-literatureUnknown135(42)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 (ε450 = 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.Journal of the American Chemical SocietySpectral evolution of a photochemical protecting group for orthogonal two-color uncaging with visible light.PMC4097017MH085498R01 NS069720R01 GM053395R01 MH085498GM053395NS069720K99 DA034648Sabatini BLBanghart MROlson JPEllis-Davies GCfalseSpectral evolution of a photochemical protecting group for orthogonal two-color uncaging with visible light.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 (ε450 = 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.2013-01-01T00:00:00Z2013 Oct2025-04-22T00:58:48.129Z2019-03-27T01:32:02ZS-EPMC40970172411706010.1021/ja408225k