- Synthesis and photocleavage of 7-[{Bis(carboxymethyl)amino}-coumarin-4-yl] methyl-caged neurotransmitters
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7-[{Bis(carboxymethyl)amino}coumarin-4-yl]methyl-caged neurotransmitters (glutamate and GABA) were synthesized. Both caged compounds showed sufficient stability in the dark, were water-soluble at pH 7.2 without using organic solvents, and exhibited relati
- Senda, Naoko,Momotake, Atsuya,Arai, Tatsuo
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- {7-[Bis(carboxymethyl)amino]coumarin-4-yl}methoxycarbonyl derivatives for photorelease of carboxylic acids, alcohols/phenols, thioalcohols/thiophenols, and amines
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Light-induced release of biomolecules from inactive precursor molecules represents a powerful method to study cellular processes with high temporal and spatial resolution. Here we report the synthesis and photochemistry of a series of {7-[bis(carboxymethyl)amino]coumarin-4-yl}methyl carboxylates, carbonates, carbamates, and thiocarbonates as potential phototriggers for compounds with COOH, OH, NH2, and SH functions. The compounds are soluble in aqueous buffer, show low fluorescence, and are efficiently photolysed by irradiation with UV/Vis or IR light to release carboxylates, alcohols, phenols, amines, thioalcohols, or thiophenols.
- Hagen, Volker,Dekowski, Brigitte,Kotzur, Nico,Lechler, Ralf,Wiesner, Burkhard,Briand, Benoit,Beyermann, Michael
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experimental part
p. 1621 - 1627
(2009/04/06)
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- Coumarinylmethyl esters for ultrafast release of high concentrations of cyclic nucleotides upon one- and two-photon photolysis
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(Chemical Equation Presented) Shedding light: Efficient activation of cyclic nucleoside monophosphates (cNMPs) can be achieved upon one- and two-photon flash photolysis of novel photolabile coumarinylmethyl esters of cAMP and cGMP (A = adenosine, G = guanosine) as well as their 8-bromosubstituted derivatives. The phototriggers show high solubility in water and permit space- and time-resolved investigations of the molecular mechanisms of cyclic nucleotide dependent processes.
- Hagen, Volker,Dekowski, Brigitte,Nache, Vasilica,Schmidt, Reinhard,Geissler, Daniel,Lorenz, Dorothea,Eichhorst, Jenny,Keller, Sandra,Kaneko, Hiroshi,Benndorf, Klaus,Wiesner, Burkhard
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p. 7887 - 7891
(2007/10/03)
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