Abstract
Excited-state intramolecular proton transfer (ESIPT)-based fluorophores with two-photon excitation fluorescence (TPEF) are rare. Our aim with this research was to develop ESIPT-based fluorophores exhibiting TPEF. Herein, we used 4-hydroxyisoindoline-1,3-dione as a scaffold to develop a two-photon fluorescent probe BHID-Bpin, for the detection of peroxynitrite (ONOO-). BHID-Bpin exhibits excellent selectivity, sensitivity, and fast response towards ONOO- in PBS buffer solution (10 mM, pH = 7.40). Additionally, BHID-Bpin displays high photo-stability under two-photon irradiation at 750 nm. Furthermore, the probe can image endogenous ONOO- in HeLa cells and exogenous ONOO- in rat hippocampal slices at a depth of 110 μm.
Highlights
Excited-state intramolecular proton transfer (ESIPT)-based fluorophores with two-photon excitation fluorescence (TPEF) are rare
Excitedstate intramolecular proton transfer (ESIPT) fluorophores are attractive for developing reaction-based fluorescent probes
Upon addition of 2 equiv. of ONOOÀ/9.5 equiv. of H2O2, a fluorescence enhancement was observed with maximum fluorescence observed at 1/80 min. These results indicated that probe BHID-Bpin has a much faster response and was more sensitive for ONOOÀ than H2O2
Summary
Excited-state intramolecular proton transfer (ESIPT)-based fluorophores with two-photon excitation fluorescence (TPEF) are rare. We used 4-hydroxyisoindoline-1,3-dione as a scaffold to develop a two-photon fluorescent probe BHID-Bpin, for the detection of peroxynitrite (ONOOÀ). The probe BHID-Bpin (10 mM) exhibits no absorption peak, upon addition of ONOOÀ (20 mM)/ H2O2 (95 mM), the probe displays a weak absorption at about 400 nm (Fig. S1 and S6, ESI†).
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