Thiol-reactive Pyrene Dimer Having A Disulfide Linkage as A Ratiometric Fluorescence Probe to Thiol-containing Biomolecules

A disulfide-linked pyrene dimer (1), which was constructed with two pyrene derivatives and a cystine-derived disulfide linker, was synthesized as a thiol-reactive ratiometric fluorescence probe. 1 alone showed strong excimer fluorescence at around 490 nm in an aqueous dimethyl sulfoxide solution. Upon addition of thiol-containing biomolecules such as l-cysteine, l-homocysteine, and glutathione, the excimer fluorescence of 1 decreased, while monomeric fluorescence increased, reflecting reduction-responsive cleavage of disulfide bond of 1 to give the corresponding thiol 2. A disulfide-linked pyrene dimer (1), which was constructed with two pyrene derivatives and a cystine-derived disulfide linker, was synthesized as a thiol-reactive ratiometric fluorescence probe. Upon addition of thiol-containing biomolecules such as l-cysteine, the excimer fluorescence of 1 decreased, while monomeric fluorescence increased, reflecting reduction-responsive cleavage of disulfide bond of 1 to give the corresponding thiol 2.