Journal
BIOSENSORS & BIOELECTRONICS
Volume 89, Issue -, Pages 919-926Publisher
ELSEVIER ADVANCED TECHNOLOGY
DOI: 10.1016/j.bios.2016.09.093
Keywords
Self-immolation; Fluorescence; In vivo; Sensing; Hydrogen sulfide
Categories
Funding
- National Research Foundation of Korea (NRF) - Korea government (MSIP) [NRF-2015R1A2A2A01007166]
- Global Frontier Project through the Center for BIoNano Health Guard - Ministry of Science, ICT and Future Planning [H-GUARD_2014M3A6B2060489]
- National Research Council of Science & Technology grant - MSIP [CAP-15-09-KIMS]
- KRIBB Initiative Research Program
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Hydrogen sulfide is a critical biological messenger, but few biologically compatible methods are available for its detection in vivo. Here, we describe the design and synthesis of a novel azide-functionalized near-infrared probe, NIR-Az, for a hydrogen sulfide assay in which a self-immolative linker is incorporated between the azide moiety and phenolic dihydroxanthene fluorophore from a cyanine dye. A large turn-on near-infrared fluorescence signal results from the reduction of the azide group of the fluorogenic moiety to an amine, in which the self-immolative linker also enhances the accessibility of NIR-Az to hydrogen sulfide. NIR-Az can select hydrogen sulfide from among 16 analytes, including cysteine, glutathione, and homocysteine. By exploiting the superior properties of NIR-Az, such as its good biocompatibility and rapid cell internalization, we successfully demonstrated its usefulness in monitoring both the concentration- and time-dependent variations of hydrogen sulfide in living cells and animals (detection limit less than 0.26 mu M), thereby providing a powerful approach for probing hydrogen sulfide chemistry in biological systems.
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