Reversible ratiometric detection of highly reactive hydropersulfides using a FRET-based dual emission fluorescent probe

Kawagoe, Ryosuke; Takashima, Ippei; Uchinomiya, Shohei; Ojida, Akio

doi:10.1039/c6sc03856e

Cited by 79 publications

(48 citation statements)

References 29 publications

(34 reference statements)

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“…In conclusion, we have designed and synthesized a FRET‐based, hydropolysulfides‐selective ratiometric fluorescent probe that is applicable for rapid (on the order of seconds) and reversible intracellular imaging and quantification of endogenous hydropolysulfides without interference from other thiols such as GSH. The high selectivity, rapid responsiveness, reversibility, and quantification ability of our probe stand in marked contrast to previously reported reversible fluorescent probes for live‐cell imaging of sulfane sulfurs or hydropersulfides, which suffer from GSH‐dependent dissociation reaction, relatively slow reaction kinetics (on the order of minutes), cross‐reactivity with physiologically relevant concentrations of GSH, and lack of quantification ability. We believe our versatile imaging tool for hydropolysulfides will open up tremendous opportunities to extend our understanding of the pathophysiological roles of RSS.…”

Section: Optical Properties Apparent Kd Values and Selectivity Of Smentioning

confidence: 58%

“…The fluorescence ratio increased immediately after addition of BnSSH, and subsequent addition of NEM resulted in rapid and complete restoration of the ratio, confirming reversibility of the reaction. The temporal resolution was on the order of seconds, which is the fastest yet reported . Interestingly, we observed a gradual increase in the basal level of the ratio when addition of BnSSH and washing with BnSSH‐free medium were repeated (Figure c,d and Video S2).…”

Section: Optical Properties Apparent Kd Values and Selectivity Of Smentioning

confidence: 70%

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A Reversible Fluorescent Probe for Real‐Time Live‐Cell Imaging and Quantification of Endogenous Hydropolysulfides

2018

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The chemical biology of reactive sulfur species, including hydropolysulfides,h as been as ubject undergoing intense study in recent years,but further understanding of their "intact" function in living cells has been limited owing to alack of appropriate analytical tools.I no rder to overcome this limitation, we developed an ew type of fluorescent probe that reversibly and selectively reacts to hydropolysulfides.T he probe enables live-cell visualization and quantification of endogenous hydropolysulfides without interference from intrinsic thiol species such as glutathione.A dditionally,r ealtime reversible monitoring of oxidative-stress-induced fluctuation of intrinsic hydropolysulfides has been achieved with at emporal resolution on the order of seconds,aresult which has not yet been realized using conventional methods.T hese results reveal the probesv ersatility as an ew fluorescence imaging tool to understand the function of intracellular hydropolysulfides.

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Section: Optical Properties Apparent Kd Values and Selectivity Of Smentioning

confidence: 58%

Section: Optical Properties Apparent Kd Values and Selectivity Of Smentioning

confidence: 70%

A Reversible Fluorescent Probe for Real‐Time Live‐Cell Imaging and Quantification of Endogenous Hydropolysulfides

2018

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“…In 2017, based on the above findings, Ojida et al reported the first example of a ratiometric fluorescent probe 24 based on Förster resonance energy transfer mechanism that can reversibly monitor intracellular hydropersulfide levels (Scheme 7). [31] This probe possesses a xanthene ring conjugated with a coumarin unit through a rigid linker, and is susceptible to intramolecular FRET photophysical process due to the spectral overlap between the fluorescence of coumarin (FRET donor) and the absorbance of xanthene (FRET acceptor).…”

Section: Nucleophilic Attack On Xanthene Ringmentioning

confidence: 99%

Reversible Reaction‐Based Fluorescent Probes for Dynamic Sensing and Bioimaging

2020

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Diverse chemical species such as ions and molecules exist within living cells and organisms undergoing dynamic changes in their local environment by a web of continuously interacting reactions. Reaction‐based fluorescent probes with a highly sought reversible feature can provide a real‐time monitor of the concentration dynamics (increases and decreases) of such chemical species, thus ideally suited to understand the physiological function, and pathogenic mechanisms of corresponding bio‐species in the regulation of cellular function and disease progression. This review summarizes the current methods for constructing reversible reaction‐based fluorescent probes. The sensing mechanisms and biological applications of these probes are also discussed. The representative examples reported recently are categorized according to the type of reversible chemical reactions utilized: nucleophilic additions (Michael additions, chromophore reactions), nucleophilic addition‐condensation reactions, and redox reactions. Finally, we present the potential challenges and suggestions for developing probes based on dynamic and reversible covalent bond formation reactions.

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“…5c) (39). When A549 cells were treated with the fluorescent probe for 20 min, bright fluorescence was observed in the cytosolic region.…”

Section: Cellular Applications Of Fluorescent Probes and Inhibitors Imentioning

confidence: 99%

Fluorescent Probes and Selective Inhibitors for Biological Studies of Hydrogen Sulfide- and Polysulfide-Mediated Signaling

Takano

Echizen

Hanaoka

2017

Antioxidants & Redox Signaling

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Significance: Hydrogen sulfide (H2S) plays roles in many physiological processes, including relaxation of vascular smooth muscles, mediation of neurotransmission, inhibition of insulin signaling, and regulation of inflammation. Also, hydropersulfide (R−S−SH) and polysulfide (−S−Sn−S−) have recently been identified as reactive sulfur species (RSS) that regulate the bioactivities of multiple proteins via S-sulfhydration of cysteine residues (protein Cys−SSH) and show cytoprotection. Chemical tools such as fluorescent probes and selective inhibitors are needed to establish in detail the physiological roles of H2S and polysulfide.Recent Advances: Although many fluorescent probes for H2S are available, fluorescent probes for hydropersulfide and polysulfide have only recently been developed and used to detect these sulfur species in living cells.Critical Issues: In this review, we summarize recent progress in developing chemical tools for the study of H2S, hydropersulfide, and polysulfide, covering fluorescent probes based on various design strategies and selective inhibitors of H2S- and polysulfide-producing enzymes (cystathionine γ-lyase, cystathionine β-synthase, and 3-mercaptopyruvate sulfurtransferase), and we summarize their applications in biological studies.Future Directions: Despite recent progress, the precise biological functions of H2S, hydropersulfide, and polysulfide remain to be fully established. Fluorescent probes and selective inhibitors are effective chemical tools to study the physiological roles of these sulfur molecules in living cells and tissues. Therefore, further development of a broad range of practical fluorescent probes and selective inhibitors as tools for studies of RSS biology is currently attracting great interest. Antioxid. Redox Signal. 27, 669–683.

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Reversible ratiometric detection of highly reactive hydropersulfides using a FRET-based dual emission fluorescent probe

Abstract: A ratiometric fluorescent probe that can visualize endogenously produced hydropersulfides has been developed.

Cited by 79 publications

References 29 publications

A Reversible Fluorescent Probe for Real‐Time Live‐Cell Imaging and Quantification of Endogenous Hydropolysulfides

A Reversible Fluorescent Probe for Real‐Time Live‐Cell Imaging and Quantification of Endogenous Hydropolysulfides

Reversible Reaction‐Based Fluorescent Probes for Dynamic Sensing and Bioimaging

Fluorescent Probes and Selective Inhibitors for Biological Studies of Hydrogen Sulfide- and Polysulfide-Mediated Signaling

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