Mitochondria-Targeted Reaction-Based Fluorescent Probe for Hydrogen Sulfide

Pak, Yen Leng; Li, Jun; Ko, Kyoung Chul; Kim, Gyoungmi; Lee, Jin Yong; Yoon, Juyoung

doi:10.1021/acs.analchem.6b00956

Cited by 217 publications

(75 citation statements)

References 85 publications

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“…333 Another H 2 S detection mechanism was described recently and is based on the thiolysis of the 7-nitro-1,2,3-benzodiazole amine moiety linked to the TPP + -linked naphthalimide fluorophore (Chart 46). 334 The reaction with H 2 S results in the formation of green-fluorescent piperazine-naphthalimide and 7-nitro-1,2,3-benzodiazole-4-thiol. However, the estimated rate constant value of the reaction of this probe with Na 2 S at pH 7.4 is low and equal to ca.…”

Section: Mitochondria-targeted Probes and Sensors For Reactive Oxymentioning

confidence: 99%

Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications

Zielonka¹,

Joseph²,

et al. 2017

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Mitochondria are recognized as one of the most important targets for new drug design in cancer, cardiovascular, and neurological diseases. Currently, the most effective way to deliver drugs specifically to mitochondria is by covalent linking a lipophilic cation such as an alkyltriphenylphosphonium moiety to a pharmacophore of interest. Other delocalized lipophilic cations, such as rhodamine, natural and synthetic mitochondria-targeting peptides, and nanoparticle vehicles, have also been used for mitochondrial delivery of small molecules. Depending on the approach used, and the potentials of cell and mitochondrial membranes, more than 1000-fold higher mitochondrial concentration can be achieved. Mitochondrial targeting has been developed to study mitochondrial physiology and dysfunction and the interaction between mitochondria and other subcellular organelles and for treatment of a variety of diseases such as neurodegeneration and cancer. In this review, we discuss efforts to target small-molecule compounds to mitochondria for probing mitochondria function, as diagnostic tools and potential therapeutics. We describe the physicochemical basis for mitochondrial accumulation of lipophilic cations, synthetic chemistry strategies to target compounds to mitochondria, mitochondrial probes and sensors, and examples of mitochondrial targeting of bioactive compounds. Finally, we review published attempts to apply mitochondria-targeted agents for the treatment of cancer and neurodegenerative diseases.

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Section: Mitochondria-targeted Probes and Sensors For Reactive Oxymentioning

confidence: 99%

Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications

Zielonka¹,

Joseph²,

et al. 2017

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“…7‐Hydroxycoumarin and NBD are considered as a suitable FRET pair, and their emission spectra are obviously separate (Figure S1). Triphenylphosphonium salt is thought to target mitochondria and has been widely used to prepare mitochondria‐targeted fluorescent probes . According to the above consideration, Probe MR‐1 was designed to selectively imaging of mitochondrial H 2 S (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

An NBD‐Based Mitochondrial Targeting Ratiometric Fluorescent Probe for Hydrogen Sulfide Detection

Wei

Guo

et al. 2019

ChemistrySelect

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Hydrogen sulfide (H2S) is an important endogenous gaseous signaling molecule with multiple biological functions. In this study, an NBD‐based ratiometric fluorescent probe (MR‐1) was successfully designed and synthesized for selectively detection H2S. The probe exhibits high selectivity and fast emission intensity ratio changes in response to H2S in solution. The modification of triphenylphosphine in the probe enables it to be used for the imaging mitochondrial H2S in living HeLa cells.

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“…The good selectivity could be well understood by the strong nucleophilic ability of HSO 3 − /SO 3 2− under neutral conditions. It was reported that HS − could react with 7-nitrobenzofurazan moiety to quench fluorescence36. So compound Donor (Supplementary Scheme 1) was used to reveal the reactivity toward HS − .…”

Section: Resultsmentioning

confidence: 99%

A new fluorescent probe for colorimetric and ratiometric detection of sulfur dioxide derivatives in liver cancer cells

Wang

Cui

et al. 2017

Sci Rep

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A new ratiometric fluorescent probe was constructed with hemicyanine and 7-nitrobenzofurazan for detection of sulfur dioxide derivatives (HSO3−/SO32−). The ratiometric response mode could be attributed to the efficient FRET (Förster resonance energy transfer) platform. The probe exbihited some desirable properties including fast response (within 2 minutes), good selectivity and high sensitivity. Moreover, the probe could detect endogenous HSO3− in liver cancer cells rather than normal liver cells, implying the diagnosal potential of the probe.

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Mitochondria-Targeted Reaction-Based Fluorescent Probe for Hydrogen Sulfide

Cited by 217 publications

References 85 publications

Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications

Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications

An NBD‐Based Mitochondrial Targeting Ratiometric Fluorescent Probe for Hydrogen Sulfide Detection

A new fluorescent probe for colorimetric and ratiometric detection of sulfur dioxide derivatives in liver cancer cells

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