Development of a long-wavelength fluorescent probe based on quinone-methide-type reaction to detect physiologically significant thiols |
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Authors: | Huang Sheng-Tung Ting Kuo-Neng Wang Kun-Li |
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Affiliation: | aInstitute of Biotechnology, National Taipei University of Technology, Taipei, Taiwan;bInstitute of Chemical Engineering, National Taipei University of Technology, Taipei, Taiwan |
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Abstract: | 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 μM range, which presents to the applicability for the construction of fiber-optic biosensors in the future clinical diagnostic. |
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Keywords: | Thiols Fluorescence probe Quinone– methide rearrangement |
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