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 microM range, which presents to the applicability for the construction of fiber-optic biosensors in the future clinical diagnostic.
Institute of Biotechnology, National Taipei University of Technology, Taipei, Taiwan. ws75624@ntut.edu.tw
Sheng-Tung
ST
Huang
Kuo-Neng
KN
Ting
Kun-Li
KL
Wang
D000596:Amino Acids / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003374:Coumarins / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry*; D045563:Indolequinones / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D010777:Photochemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D000596:Amino Acids; D003374:Coumarins; D005456:Fluorescent Dyes; D045563:Indolequinones; D013438:Sulfhydryl Compounds; C068040:quinone methide; C030123:coumarin