{7-[Bis(carboxymethyl)amino]coumarin-4-yl}methoxycarbonyl derivatives for photorelease of carboxylic acids, alcohols/phenols, thioalcohols/thiophenols, and amines.
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, NH(2), 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.
Leibniz-Institut für Molekulare Pharmakologie, Robert-Rössle-Strasse 10, 13125 Berlin, Germany. hagen@fmp-berlin.de
Volker
V
Hagen
Brigitte
B
Dekowski
Nico
N
Kotzur
Ralf
R
Lechler
Burkhard
B
Wiesner
Benoît
B
Briand
Michael
M
Beyermann
D000438:Alcohols / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D003374:Coumarins / Q000138:chemical synthesis*; D008956:Models, Chemical; D010636:Phenols / Q000737:chemistry*; D010782:Photolysis; D017319:Photosensitizing Agents / Q000138:chemical synthesis*; D012995:Solubility; D012996:Solutions / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D000438:Alcohols; D000588:Amines; D002264:Carboxylic Acids; D003374:Coumarins; D010636:Phenols; D017319:Photosensitizing Agents; D012996:Solutions; D013438:Sulfhydryl Compounds; D014867:Water; C042983:thiophenol