83489-61-6Relevant academic research and scientific papers
Structural modifications of nile red carbon monoxide fluorescent probe: Sensing mechanism and applications
Klán, Petr,Madea, Dominik,Martínek, Marek,Muchová, Lucie,Váňa, Ji?í,Vítek, Libor
, p. 3473 - 3489 (2020/03/25)
Carbon monoxide (CO) is a cell-signaling molecule (gasotransmitter) produced endogenously by oxidative catabolism of heme, and the understanding of its spatial and temporal sensing at the cellular level is still an open challenge. Synthesis, optical properties, and study of the sensing mechanism of Nile red Pd-based CO chemosensors, structurally modified by core and bridge substituents, in methanol and aqueous solutions are reported in this work. The sensing fluorescence "off-on" response of palladacycle-based sensors possessing low-background fluorescence arises from their reaction with CO to release the corresponding highly fluorescent Nile red derivatives in the final step. Our mechanistic study showed that electron-withdrawing and electron-donating core substituents affect the rate-determining step of the reaction. More importantly, the substituents were found to have a substantial effect on the Nile red sensor fluorescence quantum yields, hereby defining the sensing detection limit. The highest overall fluorescence and sensing rate enhancements were found for a 2-hydroxy palladacycle derivative, which was used in subsequent biological studies on mouse hepatoma cells as it easily crosses the cell membrane and qualitatively traces the localization of CO within the intracellular compartment with the linear quantitative response to increasing CO concentrations.
Water-soluble nile blue derivatives: syntheses and photophysical properties
Jose, Jiney,Ueno, Yuichiro,Burgess, Kevin
supporting information; experimental part, p. 418 - 423 (2009/06/19)
Four water-soluble 2-hydroxy-Nile Blue derivatives, 1a, 1b, 2a, and 2b, were prepared by condensation reactions performed under relatively mild conditions (90°C, N,N-dimethylformamide with no added acid). These fluorescent probes had more favorable fluorescence characteristics than two known water-soluble Nile Blue derivatives. Specifically, they were superior to the known dyes with respect to their quantum yields in aqueous media and the sharpness of their fluorescence emissions. Concentration-dependant UV absorption and fluorescence emission studies indicated that the dyes did not aggregate in aqueous solution at concentrations of less than 1-4 μM. The new water-soluble materials 1a, 1b, 2a, and 2b emit in a desirable region of the fluorescence spectrum (A = 670-675 nm). Overall they are potentially interesting for labeling biomolecules in aqueous environments.
