Development of a Highly Selective Fluorescence Probe for Hydrogen Sulfide

Sasakura, Kiyoshi; Hanaoka, Kenjiro; Shibuya, Norihiro; Mikami, Yuzuru; Kimura, Yoshinobu; Komatsu, Toshimitsu; Ueno, Takahiro; Terai, Takuya; Kimura, Hideo; Nagano, Tetsuo

doi:10.1021/ja207851s

Cited by 614 publications

(356 citation statements)

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“…Although the PNP probes have performed as well as the fluorescent probes reported previously [23][24][25][26][27][28] , due to the ensemble average effect, bulk measurements are intrinsically not as sensitive as single-particle measurements. The AuNR-Ag PNP with a 2.1-nm thick silver shell, for example, contains B6 Â 10 5 silver atoms, which translates to B30 mM Ag for a B50 pM PNP solution.…”

Section: Resultsmentioning

confidence: 93%

“…During the past several years, several research groups have developed sulphide-responsive fluorescent organic molecules to detect H 2 S in live cells and have achieved selective intracellular sulphide imaging with limits of detection of 1-10 mM (ref. [23][24][25][26][27][28]. Although most publications suggest that the average endogenous H 2 S level is in the mM range, much lower sulphide concentrations have been reported 29 .…”

Section: Doi: 101038/ncomms2722mentioning

confidence: 98%

“…More importantly, the anabolism and catabolism of cellular sulphide are known to be rapid, which means that the sulphide concentration could fluctuate continuously from as high as submM during its explosive production to as low as a few nM after its rapid consumption 30 . However, almost all existing H 2 Ssensing methods are based on some irreversible stoichiometric reaction between the probe and sulphide species [23][24][25][26][27][28] and cannot be utilized to monitor the dynamics of sulphide generation and elimination inside cells, especially at the single-molecule level. Therefore, more sensitive methods that are capable of following time-dependent changes in H 2 S concentrations over a large dynamic range are needed for in-depth studies of this gaseous transmitter.…”

Section: Doi: 101038/ncomms2722mentioning

confidence: 99%

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Highly sensitive sulphide mapping in live cells by kinetic spectral analysis of single Au-Ag core-shell nanoparticles

et al. 2013

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Hydrogen sulphide (H 2 S) is a gaseous signalling agent that has important regulatory roles in many biological systems but remains difficult to measure in living biological specimens. Here we introduce a new method for highly sensitive sulphide mapping in live cells via singleparticle plasmonic spectral imaging that uses Au-Ag core-shell nanoparticles as probes. This strategy is based on Ag 2 S formation-induced spectral shifts of the nanoprobes, which is not only highly selective towards sulphide but also shows a linear logarithmic dependence on sulphide concentrations from 0.01 nM to 10 mM. A theoretical model was established that successfully explained the experimental observations, suggesting that the local sulphide concentration as well as its oscillations can be determined indirectly from kinetic measurements of the spectral shifts of the nanoprobes. We demonstrated for the first time the realtime mapping of local variations of sulphide levels in live cells with nM sensitivity.

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Section: Resultsmentioning

confidence: 93%

Section: Doi: 101038/ncomms2722mentioning

confidence: 98%

Section: Doi: 101038/ncomms2722mentioning

confidence: 99%

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Highly sensitive sulphide mapping in live cells by kinetic spectral analysis of single Au-Ag core-shell nanoparticles

et al. 2013

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“…Cyclam is a tetradentate chelating ligand that binds copper, and the reactions between copper cyclam complexes and thiols are slow (t 1/2 >10 min for H 2 S; t 1/2 >1 h for glutathione). 32 The DHX fluorophore was recently introduced by Lin and co-workers 33 and is available in a single synthetic step from carbocyanine dyes and resorcinol derivatives. NIR probes can be used in combination with those that emit in the visible to perform experiments in which more than one analyte is detected at the same time.…”

Section: Imaging Hno In the Near-infrared (Nir)mentioning

confidence: 99%

Metal-Based Optical Probes for Live Cell Imaging of Nitroxyl (HNO)

Rivera‐Fuentes

Lippard

2015

Acc. Chem. Res.

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Conspectus: Nitroxyl (HNO) is a biological signaling agent that displays distinctive reactivity compared to nitric oxide (NO). As a consequence, these two reactive nitrogen species trigger different physiological responses. Selective detection of HNO over NO has been a challenge for chemists, and several fluorogenic molecular probes have been recently developed with that goal in mind. Common constructs take advantage of the HNO-induced reduction of Cu(II) to Cu(I).The sensing mechanism of such probes relies on the ability of the unpaired electron in a d orbital of the Cu(II) center to quench the fluorescence of a photoemissive ligand by either an electron or energy transfer mechanism. Experimental and theoretical mechanistic studies suggest that proton-coupled electron transfer mediates this process, and careful tuning of the copper coordination environment has led to sensors with optimized selectivity and kinetics.The current optical probes cover the visible and near-infrared regions of the spectrum. This palette of sensors comprises structurally and functionally diverse fluorophores such as coumarin 2 (blue/green emission), boron dipyrromethane (BODIPY, green emission), benzoresorufin (red emission), and dihydroxanthenes (near-infrared emission). Many of these sensors have been successfully applied to detect HNO production in live cells. For example, copper-based optical probes have been used to detect HNO production in live mammalian cells that have been treated with H 2 S and various nitrosating agents. These studies have established a link between HSNO, the smallest S-nitrosothiol, and HNO. In addition, a near-infrared HNO sensor has been used to perform multicolor/multianalyte microscopy, revealing that exogenously applied HNO elevates the concentration of intracellular mobile zinc. This mobilization of zinc ions is presumably a consequence of nitrosation of cysteine residues in zinc-chelating proteins such as metallothionein.Future challenges for the optical imaging of HNO include devising probes that can detect HNO reversibly, especially because ratiometric imaging can only report equilibrium concentrations when the sensing event is reversible. Another important aspect that needs to be addressed is the creation of probes that can sense HNO in specific subcellular locations. These tools would be useful to identify the organelles in which HNO is produced in mammalian cells and probe the intracellular signaling networks in which this reactive nitrogen species is involved. In addition, near-infrared emitting probes might be applied to detect HNO in thicker specimens, such as acute tissue slices and even live animals, enabling the investigation of the roles of HNO in physiological or pathological conditions in multicellular systems.

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“…81,[84][85][86][87][88] Recent reports described several small-molecule fluorescent probes for H 2 S detection in living systems. [89][90][91][92][93][94] All these designs are based on H 2 S-specific reactions. A reaction-based FP sensor for H 2 S was also constructed by Chen and co-workers.…”

Section: Hydrogen Sulfide (H 2 S) Sensorsmentioning

confidence: 99%