A turn-on fluorescent probe for imaging lysosomal hydrogen sulfide in living cells

Qiao, Qinglong; Zhao, Miao; Lang, Haijing; Mao, Deqi; Cui, Jingnan; Xu, Zhaochao

doi:10.1039/c4ra03725a

Cited by 50 publications

(23 citation statements)

References 44 publications

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“…Reporters for H 2 S based on coumarin ( 8-9 ), 70,71,72 2-(2-aminophenyl)benzothiazole ( 10 ), 73 7-nitrobenz-2-oxa-1,3-diazole ( 11 ), 74 dicyanomethylenedihydrofuran ( 12 ), 75 resorufamine ( 13 ), 76 BODIPY ( 14 ), 77 phenanthroimidazole ( 15 ), 78 and the 1,8-naphthalimide scaffold ( 16 ) 79 have been described, including a lysosomally-targeted derivative ( 17 ). 80 The Pluth laboratory has also developed the first chemiluminescent H 2 S probe 18 based on an azido derivative of luminol, which can be used to detect enzymatically-produced H 2 S in vitro . 81 A near-infrared (near-IR) probe 19 based on dicyanomethylene-4H-chromene that can also be used for two-photon imaging was reported simultaneously by Xu and Peng and their co-workers.…”

Section: H2s Probesmentioning

confidence: 99%

Chemical probes for molecular imaging and detection of hydrogen sulfide and reactive sulfur species in biological systems

et al. 2015

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Hydrogen sulfide (H2S), a gaseous species produced by both bacteria and higher eukaryotic organisms, including mammalian vertebrates, has attracted attention in recent years for its contributions to human health and disease. H2S has been proposed as a cytoprotectant and gasotransmitter in many tissue types, including mediating vascular tone in blood vessels as well as neuromodulation in the brain. The molecular mechanisms dictating how H2S affects cellular signaling and other physiological events remain insufficiently understood. Furthermore, the involvement of H2S in metal-binding interactions and formation of related RSS such as sulfane sulfur may contribute to other distinct signaling pathways. Owing to its widespread biological roles and unique chemical properties, H2S is an appealing target for chemical biology approaches to elucidate its production, trafficking, and downstream function. In this context, reaction-based fluorescent probes offer a versatile set of screening tools to visualize H2S pools in living systems. Three main strategies used in molecular probe development for H2S detection include azide and nitro group reduction, nucleophilic attack, and CuS precipitation. Each of these approaches exploit the strong nucleophilicity and reducing potency of H2S to achieve selectivity over other biothiols. In addition, a variety of methods have been developed for the detection of other reactive sulfur species (RSS), including sulfite and bisulfite, as well as sulfane sulfur species and related modifications such as S-nitrosothiols. Access to this growing chemical toolbox of new molecular probes for H2S and related RSS sets the stage for applying these developing technologies to probe reactive sulfur biology in living systems.

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Section: H2s Probesmentioning

confidence: 99%

Chemical probes for molecular imaging and detection of hydrogen sulfide and reactive sulfur species in biological systems

et al. 2015

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“…[150] To clarify the role of H 2 Si nl ysosomes,X ua nd co-workers introduced in 2013 the naphthalimide-based probe Lyso-NHS (65 a,S cheme 24), which could quantitatively determine H 2 S species inside the lysosomes of live cells.L yso-NHS localizes in lysosomes through the morpholine group and responds to H 2 St hrough the rapid thiolysis of the dinitrophenyl ether, which is as trong fluorescence quencher,u nder physiological conditions. [152] Other lysosome-targeting H 2 Sp robes (65 c [153a] and 65 d, [153b] Scheme 24) were also separately investigated. [152] Other lysosome-targeting H 2 Sp robes (65 c [153a] and 65 d, [153b] Scheme 24) were also separately investigated.…”

Section: Lytafps For Reactive Species and Thiolsmentioning

confidence: 99%

Discerning the Chemistry in Individual Organelles with Small‐Molecule Fluorescent Probes

et al. 2016

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Principle has it that even the most advanced super-resolution microscope would be futile in providing biological insight into subcellular matrices without well-designed fluorescent tags/probes. Developments in biology have increasingly been boosted by advances of chemistry, with one prominent example being small-molecule fluorescent probes that not only allow cellular-level imaging, but also subcellular imaging. A majority, if not all, of the chemical/biological events take place inside cellular organelles, and researchers have been shifting their attention towards these substructures with the help of fluorescence techniques. This Review summarizes the existing fluorescent probes that target chemical/biological events within a single organelle. More importantly, organelle-anchoring strategies are described and emphasized to inspire the design of new generations of fluorescent probes, before concluding with future prospects on the possible further development of chemical biology.

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“…Naphthalimide dye is the favorable building block for constructing fluorescent probes because of its excellent photophysical properties, such as high extinction coefficients, excellent quantum yields, and great photostability. In addition, azido group is well-known for sensitively and selectively responding to H 2 S, the electron withdrawing azide is very easy reduced by H 2 S affording the electron donating amine [17][18][19][20][21][22][23][24][25][26]. Thus, in this work, we employed the naphthalimide chromophore as the signal reporter and azido group as the responding site for H 2 S to construct a H 2 S probe based on internal charge transfer (ICT) process (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

An ICT-Based Hydrogen Sulfide Sensor with Good Water Solubility for Fluorescence Imaging in Living Cells

Wei

et al. 2015

J Fluoresc

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A turn-on fluorescent probe for imaging lysosomal hydrogen sulfide in living cells

Abstract: A 1,8-naphthalimide-derived fluorescent probe for lysosomal H2S based on the reduction of azide is reported.

Cited by 50 publications

References 44 publications

Chemical probes for molecular imaging and detection of hydrogen sulfide and reactive sulfur species in biological systems

Chemical probes for molecular imaging and detection of hydrogen sulfide and reactive sulfur species in biological systems

Discerning the Chemistry in Individual Organelles with Small‐Molecule Fluorescent Probes

An ICT-Based Hydrogen Sulfide Sensor with Good Water Solubility for Fluorescence Imaging in Living Cells

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