Detection of Tyrosinase in Real Food Samples and Living Cells by a Novel Near-Infrared Fluorescence Probe.

Abstract

A new near-infrared fluorescence probe was developed and applied to the fluorescence detection of tyrosinase in real food samples and living cells. The probe (E)-2-(2-(6-((3-hydroxybenzyloxy)carbonylamino)-2,3-dihydro-1H-xanthen-4-yl)vinyl)-3,3-dimethyl-1-propyl-3H-indolium (1) was designed and synthesized by coupling 3-hydroxybenzyl alcohol via carbamate bond with an amino hemicyanine skeleton, based on the high anti-interference ability of 3-hydroxybenzyl alcohol to reactive oxygen species and its binding affinity to tyrosinase. Compared with the existing tyrosinase probes, the proposed probe exhibits superior analytical performance, such as high selectivity, high sensitivity, superior spatiotemporal sampling ability, fluorescence signal switching at 706 nm, and low detection limit of 0.36 U mL-1. More importantly, the probe has been successfully used to monitor tyrosinase in the browning of apple slices for the first time, and the results indicated that the strongest fluorescence intensity could be achieved at 2.5 h to realize precise visual recognition of tyrosinase. Notably, the probe determined tyrosinase in real food samples (apple, banana, cheese, and red wine) with a stable average recovery range of 95.7-108.3% and has been successfully used to monitor tyrosinase in the living B16 cells. The superior properties of the probe make it of great potential use in food nutritional value evaluation and clinical diagnosis of melanin-related diseases.