A D-π-A-based near-infrared fluorescent probe with large Stokes shift for the detection of cysteine in vivo

Abstract

D-π-A dyes are an ideal strategy for building near-infrared fluorescent probes that have a large Stokes shift due to their excellent properties of adjustable emission wavelength and Stokes shift. Developing a near-infrared (NIR) fluorescent probe (JTPQ-Cys) capable of detecting cysteine (Cys) was the aim of this study. In JTPQ-Cys, julolidine served as the electron donor (D) and quinoline as the electron acceptor (A), with 3,4-ethylenedioxythiophene as the π-bridge. The π-conjugation and vibrational/rotational activity of the molecule were increased by the introduction of 3,4-ethylenedioxythiophene, causing the molecule to exhibit NIR emission and a large Stokes shift. When JTPQ-Cys was used to detect Cys, a clear fluorescence turn-on signal was observed at 741 nm, together with a Stokes shift of 268 nm. The limit of detection of JTPQ-Cys for Cys is 24 nM. Moreover, JTPQ-Cys has been utilized successfully for imaging studies of Cys in cells and zebrafish because it has good photostability, low cytotoxicity, and a high signal-to-noise ratio. Overall, our findings demonstrate the potential of JTPQ-Cys to be one of the best choices for detecting Cys in biological systems, and JTPQ is an ideal fluorophore to construct fluorescence dyes for bioimaging.