72433-26-2Relevant articles and documents
Dual-color control of nucleotide polymerization sensed by a fluorescence actuator
Reimao-Pinto, Madalena M.,Cordeiro, Ana,Almeida, Carina,Pinheiro, Andre V.,Moro, Artur,Lima, Joao C.,Baptista, Pedro V.
, p. 751 - 756 (2014/05/06)
Spatial and temporal control of molecular mechanisms can be achieved using photolabile bonds that connect biomolecules to protective caging groups, which can be cleaved upon irradiation of a specific wavelength, releasing the biomolecule ready-to-use. Here we apply and improve a previously reported strategy to tightly control in vitro transcription reactions. The strategy involves two caging molecules that block both ATP and GTP nucleotides. Additionally, we designed a molecular beacon complementary to the synthesized mRNA to infer its presence through a light signal. Upon release of both nucleotides through a specific monochromatic light (390 and 325 nm) we attain a light signal indicative of a successful in vitro transcription reaction. Similarly, in the absence of irradiation, no intense fluorescence signal was obtained. We believe this strategy could further be applied to DNA synthesis or the development of logic gates. This journal is
Coumarin-4-ylmethoxycarbonyls as Phototriggers for Alcohols and Phenols
Suzuki, Akinobu Z.,Watanabe, Takayoshi,Kawamoto, Mika,Nishiyama, Keiko,Yamashita, Hirotaka,Ishii, Megumi,Iwamura, Michiko,Furuta, Toshiaki
, p. 4867 - 4870 (2007/10/03)
(Equation Presented) Caged compounds can be used to regulate the spatial and temporal dynamics of signaling molecules in live cells. Photochemical properties of coumarin-4-ylmethoxy carbonates (1a-d) are investigated to construct caged compounds of hydroxy-containing molecules. All the compounds possess desired properties as phototriggers for alcohols and phenols. The 6-bromo-7-hydroxycoumarin-4-ylmethoxycarbonyl (Bhcmoc) group has the highest photochemical efficiency and is applied to make caged compounds of 1,2-dioctanoylglycerol (diC8), Tyr-OMe, and adenosine.
Deactivation behavior and excited-state properties of (coumarin-4-yl)methyl derivatives. 2. Photocleavage of selected (coumarin-4-yl)methyl-caged adenosine cyclic 3′,5′-monophosphates with fluorescence enhancement
Eckardt, Torsten,Hagen, Volker,Schade, Bjoern,Schmidt, Reinhardt,Schweitzer, Claude,Bendig, Juergen
, p. 703 - 710 (2007/10/03)
A series of axial and equatorial diastereomers of (coumarin-4-yl)methyl-caged adenosine cyclic 3′,5′-monophosphates (cAMPs), 1-6, having methoxy, dialkylamino, or no substituent in the 6- and/or 7-positions, and their corresponding 4-(hydroxymethyl)coumarin photoproducts 7-12 have been synthesized. The photochemical and UV/vis spectroscopical properties (absorption and fluorescence) of 1-6 and 7-12 have been examined in methanol/aqueous HEPES buffer solution. Donor substitution in the 6-position causes a strong bathochromic shift of the long-wavelength absorption band, whereas substitution in the 7-position leads only to a weak red shift. The photochemical cleavage of the caged cAMPs was investigated, and the photoproducts were analyzed. Photochemical quantum yields, fluorescence quantum yields, and lifetimes of the excited singlet states were determined. The highest values of photochemical quantum yields (photo-SN1 mechanism) were obtained with caged cAMPs having a donor substituent in the 7-position of the coumarin moiety, caused by electronic stabilization of the intermediately formed coumarinylmethyl cation. With donor substitution in the 6-position, the resulting moderate electronic stabilization of the coumarinylmethyl cation is overcompensated by the strong bathochromic shift, reducing the energy gap between the excited-state S1 and the corresponding coumarinylmethyl cation. The rate constant for the ester cleavage and liberation of cAMP is about 109 s-1, estimated for the axial isomer of 6 by analysis of the fluorescence increase of the alcohol 12 formed upon laser pulse photolysis.
