Development of a highly selective fluorescence probe for hydrogen sulfide.

Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Journal of the American Chemical Society (Impact Factor: 10.68). 11/2011; 133(45):18003-5. DOI: 10.1021/ja207851s
Source: PubMed

ABSTRACT Hydrogen sulfide (H(2)S) has recently been identified as a biological response modifier. Here, we report the design and synthesis of a novel fluorescence probe for H(2)S, HSip-1, utilizing azamacrocyclic copper(II) ion complex chemistry to control the fluorescence. HSip-1 showed high selectivity and high sensitivity for H(2)S, and its potential for biological applications was confirmed by employing it for fluorescence imaging of H(2)S in live cells.

  • [Show abstract] [Hide abstract]
    ABSTRACT: A fluorescent off-on probe for H2S was exploited by coupling the azide-based strategy with the excited-state intramolecular proton transfer (ESIPT) sensing mechanism, which exhibits a considerably high fluorescence enhancement (1150-fold), an extremely low detection limit (0.78 nM), and a relatively fast response time (3-10 min) as well as excellent selectivity.
    Chemical Communications 03/2014; · 6.38 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: Hydrogen sulfide (H2 S) is connected with various physiological and pathological functions. However, understanding the important functions of H2 S remains challenging, in part because of the lack of tools for detecting endogenous H2 S. Herein, compounds Ratio-H2 S 1/2 are the first FRET-based mitochondrial-targetable dual-excitation ratiometric fluorescent probes for H2 S on the basis of H2 S-promoted thiolysis of dinitrophenyl ether. With the enhancement of H2 S concentration, the excitation peak at λ≈402 nm of the phenolate form of the hydroxycoumarin unit drastically increases, whereas the excitation band centered at λ≈570 nm from rhodamine stays constant and can serve as a reference signal. Thus, the ratios of fluorescence intensities at λ=402 and 570 nm (I402 /I570 ) exhibit a drastic change from 0.048 in the absence of H2 S to 0.36 in the presence of 180 μM H2 S; this is a 7.5-fold variation in the excitation ratios. The favorable properties of the probe include the donor and acceptor excitation bands, which exhibit large excitation separations (up to 168 nm separation) and comparable excitation intensities, high sensitivity and selectivity, and function well at physiological pH. In addition, it is demonstrated that the probe can localize in the mitochondria and determine H2 S in living cells. It is expected that this strategy will lead to the development of a wide range of mitochondria-targetable dual-excitation ratiometric probes for other analytes with outstanding spectral features, including large separations between the excitation wavelengths and comparable excitation intensities.
    Chemistry - An Asian Journal 04/2014; · 4.57 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: A kinetically stable Eu(iii) complex for the detection of sulfide in water is reported. The probe shows excellent selectivity and fast reaction time. Its long-lived luminescence makes this the first probe for the time-gated detection of sulfide in complex biological samples.
    Chemical Communications 03/2014; · 6.38 Impact Factor


Available from