ChemComm
Communication
concentrations of biothiols. Preliminary fluorescence imaging
experiments in cells indicate its potential to probe H2S chem-
istry in biological systems.
Notes and references
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Fig. 5 (A) Fluorescence response of 1 (5 mM) to HSÀ (100 mM) and biothiols Cys
(0.5 mM), Hcy (0.5 mM), and GSH (1 mM) in PBS buffer (10 mM, pH 7.4, containing
20 mM CTAB). Red bar: 1 + biothiols; green bar: 1 + biothiols + H2S. lex = 455 nm,
l
em = 517 nm. Slits: 5/5 nm. (B) The corresponding fluorescent images: (1) 1 only;
(2) 1 + HSÀ; (3) 1 + Cys; (4) 1 + Cys + HSÀ; (5) 1 + Hcy; (6) 1 + Hcy + HSÀ; (7) 1 + GSH;
(8) 1 + GSH + HSÀ.
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Fig. 6 Images of H2S in COS-7 cells using probe 1 (5 mM) at 37 1C. (A)
Fluorescence image of COS-7 cells incubated with 1 for 30 min. (B) Fluorescence
image of COS-7 cells incubated with 1 for 30 min and further incubated with
NaHS (100 mM) for 30 min. (C) Fluorescence image of COS-7 cells incubated with 1
for 30 min and further incubated with NaHS (100 mM) for 30 min in the presence
of CTAB (1 mM). (D–F) The corresponding bright-field images. Scale bar: 20 mm.
experiments in the presence of biothiols. In fact, when H2S
(100 mM) and biothiols (for Cys and Hcy: 500 mM; for GSH:
1 mM) coexisted, we observed almost the same fluorescence
enhancement as that only treated by 100 mM H2S (Fig. 5A).
Moreover, the H2S-induced obvious fluorescence enhancement
in the presence of biothiols was observable by the naked eyes
(Fig. 5B). Thus, probe 1 was not consumed by biothiols, and
could be used to selective sensing of H2S in the presence of a
high concentration of biothiols.
Encouraged by the above results, we subsequently tested the
capability of 1 to image H2S in biological systems. COS-7 cells,
incubated with 1 (5 mM) in culture medium for 30 min at 37 1C,
showed almost no fluorescence (Fig. 6A), indicating that bio-
logical species, especially biothiols, did not cause inter-
ference. However, strong fluorescence in the cells was observed
after the cells were pretreated with 1 for 30 min and further
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incubated with NaHS (100 mM) for 30 min (Fig. 6B). Moreover, 10 Y. Chen, C. Zhu, Z. Yang, J. Chen, Y. He, Y. Jiao, W. He, L. Qiu, J. Cen
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we could observe stronger fluorescence when the cells were
further treated with 1 mM CTAB (Fig. 6C). These results
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indicated that probe 1 has the potential to visualize H2S levels
in living cells.
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In summary, a reaction-type fluorescent probe 1 for detec-
tion of H2S in aqueous solution was exploited through inte-
gration of a new H2S trap group 2-(iodomethyl)benzoate and a
potential fluorescent reporter methylfluorescein. The probe can
highly selectively detect H2S even in the presence of millimolar
12 It is known that in aqueous state under the physiological pH of 7.4,
the major form of H2S exists as HSÀ, and the ratio of HSÀ/H2S is
approximately 3 : 1. O. Kabil and R. Banerjee, J. Biol. Chem., 2010,
285, 21903.
c
This journal is The Royal Society of Chemistry 2013
Chem. Commun., 2013, 49, 11305--11307 11307