380663-64-9Relevant academic research and scientific papers
On the chemical reactivity of tricyanofuran(TCF)-based near-infrared fluorescent redox probes – Effects of glutathione on the probe response and product fluorescence
Siarkiewicz, Przemys?aw,Michalski, Rados?aw,Sikora, Adam,Smulik-Izydorczyk, Renata,Szala, Marcin,Grzelakowska, Aleksandra,Modrzejewska, Julia,Bailey, Asha,Nycz, Jacek E.,Kalyanaraman, Balaraman,Malecki, Jan Grzegorz,Zielonka, Jacek,Podsiad?y, Rados?aw
, (2021/05/10)
Recent research towards the development of the redox probes for in vivo applications focuses on near-infrared fluorescent sensors and tricyanofuran-based fluorophores gained popularity thanks to their favorable spectral properties. The tricyanofuran-based boronate probe (TCF-BA) has been proposed for specific fluorescent detection of selected biological oxidants in vitro and in vivo. Here, we report the detailed chemical reactivity of TCF-BA toward hydrogen peroxide, hypochlorite, and peroxynitrite in the presence and absence of glutathione, a major small molecule biothiol present intracellularly at millimolar concentrations. We demonstrate that, at the physiologically relevant concentration of glutathione, the TCF-BA probe forms an adduct, resulting in decreased reactivity of the probe toward the oxidants tested. Only peroxynitrite efficiently oxidizes TCF-BA in the presence of GSH. Furthermore, the fluorescent phenolic oxidation product, TCF-OH, also reacts with glutathione, which results in a decreased fluorescence intensity. This observation suggests that the results reported with TCF-based probes may be affected by the changes in intracellular glutathione, in addition to the desired analyte. We also report a modified probe (TCF-BA-2) derived from 1-naphthalene boronic acid, which has similar reactivity toward peroxynitrite. Although the TCF-BA-2 probe also reacts with glutathione, the absorption spectrum of its oxidation product, TCF–OH–2, is not influenced by glutathione and, therefore, can be applied for real-time monitoring of peroxynitrite formation in biological systems.
Azido push-pull fluorogens photoactivate to produce bright fluorescent labels
Lord, Samuel J.,Lee, Hsiao-Lu D.,Samuel, Reichel,Weber, Ryan,Liu, Na,Conley, Nicholas R.,Thompson, Michael A.,Twieg, Robert J.,Moerner
, p. 14157 - 14167 (2011/04/24)
Dark azido push-pull chromophores have the ability to be photoactivated to produce bright fluorescent labels suitable for single-molecule imaging. Upon illumination, the aryl azide functionality in the fluorogens participates in a photochemical conversion to an aryl amine, thus restoring charge-transfer absorption and fluorescence. Previously, we reported that one compound, DCDHF-V-P-azide, was photoactivatable. Here, we demonstrate that the azide-to-amine photoactivation process is generally applicable to a variety of push-pull chromophores, and we characterize the photophysical parameters including photoconversion quantum yield, photostability, and turn-on ratio. Azido push-pull fluorogens provide a new class of photoactivatable singlemolecule probes for fluorescent labeling and super-resolution microscopy. Lastly, we demonstrate that photoactivated push-pull dyes can insert into bonds of nearby biomolecules, simultaneously forming a covalent bond and becoming fluorescent (fluorogenic photoaffinity labeling).
