Mitochondria-Targeting Chromogenic and Fluorescence Turn-On Probe for the Selective Detection of Cysteine by Caged Oxazolidinoindocyanine

Abstract

We report a chromogenic and fluorescence turn-on probe based on crotonoyl ester-functionalized oxazolidinoindole for the selective detection of cysteine in neutral buffer. The probe rapidly formed indocyanophenolate through the Michael addition and a subsequent cyclization reaction of cysteine, inducing both a dramatic bathochromic shift (>130 nm) and a large fluorescence turn-on response (F/F0 12) in the UV-vis and fluorescence spectra and affording a micromolar limit of detection (LOD = 5.0 μM) of cysteine in HEPES buffer. When cysteine was added, the probe exhibited a dual optical change with strong green fluorescence and dramatic red color by the oxazolidinoindole-to-hydroxyethylindolium transformation. Further cellular application of the probe was successfully performed for the mitochondrial imaging of HeLa cells.