Two-photon fluorescence microscopy has become an indispensable
technique for cellular imaging. Whereas most two-photon fluorescent
probes rely on well-known fluorophores, here we report a new fluorophore
for bioimaging, namely azulene. A chemodosimeter, comprising a boronate
ester receptor motif conjugated to an appropriately substituted azulene,
is shown to be an effective two-photon fluorescent probe for reactive
oxygen species, showing good cell penetration, high selectivity for
peroxynitrite, no cytotoxicity, and excellent photostability.
N-Heterocyclic carbene (NHC) boranes undergo oxidative hydrolysis to give imidazolium salts with excellent kinetic selectivity for HOCl over other reactive oxygen species (ROS), including peroxides and peroxynitrite. Selectivity for HOCl results from the electrophilic oxidation mechanism of NHC boranes, which stands in contrast to the nucleophilic oxidation mechanism of arylboronic acids with ROS. The change in polarity that accompanies the conversion of NHC boranes to imidazolium salts can control the formation of emissive excimers, forming the basis for the design of the first fluorescence probe for ROS based on the oxidation of B-H bonds. Two-photon microscope (TPM) ratiometric imaging of HOCl in living cells and tissues is demonstrated.
The ratiometric fluorescent probe B6S, which contains pyrene as a fluorophore and imidazoline-2-thione as a reactive site, was developed for detection of hypochlorite (OCl). B6S displays a high specificity toward OCl in contrast to other reactive oxygen species and reactive nitrogen species. The probe has a low detection limit and operates under biological conditions. Moreover, the low cytotoxicity of B6S enables it to be utilized effectively for OCl imaging in living cells and tissues by using two-photon microscopy. The findings indicate that B6S has the capability of serving as a probe to explore the biological functions of OCl in living systems.
A new quinone propionic acid locked TP fluorophore which can be used for human NAD(P)H:quinone oxidoreductase (hNQO1) detection was developed. The probe, TPQ, which displays high selectivity and anti-interference ability, was successfully applied to endogenous hNQO1 imaging and for the identification of different cancer cells.
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