A highly sensitive fluorescent probe for fast recognization of DTT and its application in one- and two-photon imaging.

As a widely used reducing agent, 1, 4-dithiothreitol (DTT) plays important roles in the fields of biology, biochemistry, and biomedicine. The development of facile and fast methods for DTT detection is urgent and necessary. In this article, we rationally constructed a novel two-photon fluorescent probe 6-(methylsulfinyl)-2-phenyl-1H-benzo[de]isoquinoline-1,3(2 H)-dione (NC-DTT) for detecting DTT, which employed the 1,8-naphthalimide and sulfoxide as the fluorophore and receptor unit respectively. The sulfoxide group in probe NC-DTT can be reduced by DTT to compound 6-(methylthio)-2-phenyl-1H-benzo[de]isoquinoline-1,3(2 H)-dione (NC), which could emit strong fluorescence with large Stokes shift presumably due to the enhanced intramolecular charge transfer (ICT). This probe responded to DTT quickly (within 1000 s) and showed satisfactory selectivity. A good linearity between fluorescence intensity and the concentration of DTT in the range of 0 - 700 μM was observed, and the detection limit towards DTT was 1.4 × 10 M. Furthermore, the probe was successfully employed in one- and two-photon imaging of DTT in HepG2 cells with low cytotoxicity.