Near-infrared and naked-eye fluorescence probe for direct and highly selective detection of cysteine and its application in living cells.

Abstract

The near-infrared (NIR) fluorescence sensor for rapid, selective, and sensitive detection of cystenine (Cys) is of great importance in both biological and environmental sciences. Herein, we report a specific probe with turn-on fluorescence property, visible color change with naked-eye, and large wavelength shift on UV spectra for highly selective detection of Cys over homocysteine (Hcy) and glutathione (GSH) in both HEPES buffer (10 mM, pH 7.4) and diluted human serum. The probe based on the conjugate addition-cyclization reaction has a low limit of detection to Cys (0.16 μM as NIR fluorescence sensor and 0.13 μM as UV sensor). Kinetic study indicated that the probe has a very rapid response to Cys, owing to the much higher pseudo-first-order reaction constant with Cys (299 M(-1) s(-1)) than with Hcy (1.29 M(-1) s(-1)) or GSH (0.53 M(-1) s(-1)). Upon addition of Cys to a solution of the probe, the color changed from purple to cyan, with the maximum wavelength shifting from 582 to 674 nm in the UV spectrum and a fluorescence emission at 697 nm appearing. It has been successfully applied for determination of Cys in diluted serum and bioimaging of Cys in living cells with low cell toxicity.