A novel dual-function fluorescent probe for the detection of cysteine and its applications in vitro.

ABSTRACT

A fluorescent probe of both colorimetric and ratiometric type for highly selective and sensitive detection of Cys (cysteine) is very important in biological analysis. In this work, a new colorimetric and ratiometric fluorescent probe ((E)-2-(2-(5-(4-(acryloyloxy)phenyl)furan-2-yl)vinyl)-3-methylbenzo[d]thiazol-3-ium iodide, LP-1) was designed and synthesized for the detection of Cys. The reaction mechanism of LP-1 toward Cys involves a conjugate addition reaction between Cys and the α,ß-unsaturated carbonyl group, leading to the formation of an intermediate thioether, followed by intramolecular cyclization to produce the desired compounds LP-1-OH. At this point, the ICT process is activated, significantly increasing the fluorescence intensity of the molecules. Meanwhile, LP-1 is highly selective and sensitive to Cys identification under optimized experimental conditions. LP-1 shows a good linear relationship in the range of Cys concentration from 0.40 µM to 40 µM (R2 = 0.9942) and the limit of detection (LOD) of Cys is 0.19 µM. In addition, we have developed a simple, portable and low-cost smartphone-based high-sensitivity Cys detection method based on naked eye obvious color detection. LP-1 also has low cell toxicity and can be successfully used for biological imaging of Cys, suggesting that it is a promising biological application tool for Cys detection.