Development of a long-wavelength fluorescent probe based on quinone-methide-type reaction to detect physiologically significant thiols

We synthesized a new long-wavelength latent fluorimetric probe BCC (6) to detect physiologically significant thiols. The fluorogenic chemical transformation of BCC triggered by thiols is through a tandem reaction, thiol-induced benzoquinone reduction, and quinone-methide-type rearrangement reaction, which are spontaneous and irreversible at physiological temperature in aqueous media. The fluorescence signal revealed by this process is specific and exhibited in the near-red spectrum region with emission maxima at 595 nm, and it could be competitively inhibited by thiols scavenger, N-ethylmaleimide. The fluorescent response of BCC is insensitive to various non-thiol amino acids and biological reductants. This novel fluorimetric probe demonstrates a good relationship in detecting thiols in 1-100 mu M range, which presents to the applicability for the construction of fiber-optic biosensors in the future clinical diagnostic. (c) 2008 Elsevier B.V. All rights reserved.