A cyanine-based colorimetric and fluorescence probe for detection of hydrogen sulfide in vivo

Wang, Huan; Yang, Dan; Tan, Rui; Zhou, Zhang Jian; Xu, Rui; Zhang, Jun Feng; Zhou, Ying

doi:10.1016/j.snb.2017.03.030

Cited by 39 publications

(11 citation statements)

References 17 publications

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“…Bright-field images (top) and fluorescence images (bottom) in C. elegans : (A, E) probe 35 only; (B, F) probe 35 + 1 equiv of H 2 S; (C, G) probe 35 + 2 equiv of H 2 S; and (D, H) probe 35 + 3 equiv of H 2 S. Adapted with permission from ref . Copyright 2017 Elsevier.…”

Section: Small-molecule-based Nir Probesmentioning

confidence: 99%

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Sensing and Bioimaging of the Gaseous Signaling Molecule Hydrogen Sulfide by Near-Infrared Fluorescent Probes

et al. 2020

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A fluorescent probe for the monitoring of H 2 S levels in living cells and organisms is highly desirable. In this regard, nearinfrared (NIR) fluorescent probes have emerged as a promising tool. NIR-I and NIR-II probes have many significant advantages; for instance, NIR light penetrates deeper into tissue than light at visible wavelengths, and it causes less photodamage during biosample analysis and less autofluorescence, enabling higher signal-to-background ratios. Therefore, it is expected that fluorescent probes having emission in the NIR region are more suitable for in vivo imaging. Consequently, a considerable increase in reports of new H 2 Sresponsive NIR fluorescent probes appeared in the literature. This review highlights the advances made in developing new NIR fluorescent probes aimed at the sensitive and selective detection of H 2 S in biological samples. Their applications in real-time monitoring of H 2 S in cells and in vivo for bioimaging of living cells/animals are emphasized. The selection of suitable dyes for designing NIR fluorescent probes, along with the principles and mechanisms involved for the sensing of H 2 S in the NIR region, are described. The discussions are focused on small-molecule and nanomaterialsbased NIR probes.

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Section: Small-molecule-based Nir Probesmentioning

confidence: 99%

“…Wang et al 89 reported a colorimetric and fluorescent probe, 35, based on the disulfide bond group bridged between two hydroxy cyanine dyes. Breaking the disulfide bond and an intramolecular cyclization that promoted a 25-fold increase in fluorescence and color change was observed.…”

mentioning

confidence: 99%

Sensing and Bioimaging of the Gaseous Signaling Molecule Hydrogen Sulfide by Near-Infrared Fluorescent Probes

et al. 2020

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“…reported a cyanine‐based colorimetric fluorescent probe 28 (Figure 17). [ 106 ] A disulfide bond was introduced into the hydroxycyanine fluorophore. Due to nucleophilic attack of the hydrosulfide anion, the disulfide bond of the probe 28 was cleaved and a nucleophilic sulfhydryl group was generated, which further attacked the adjacent ester bond, and finally released the fluorophore ( λ em = 633 nm, 25‐fold).…”

Section: Fluorescent Probes Based On Dual Nucleophilic Reactionsmentioning

confidence: 99%

A review: Red/near‐infrared (NIR) fluorescent probes based on nucleophilic reactions of H₂S since 2015

et al. 2020

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The topics of human health and disease are always the focus of much attention. Hydrogen sulfide (H2S), as a double‐edged sword, plays an important role in biological systems. Studies have revealed that endogenous H2S is important to maintain normal physiological functions. Conversely, abnormal levels of H2S may contribute to various diseases. Due to the importance of H2S in physiology and pathology, research into the effects of H2S has been active in recent years. Fluorescent probes with red/near‐infrared (NIR) emissions (620–900 nm) are more suitable for imaging applications in vivo, because of their negligible photodamage, deep tissue penetration, and maximum lack of interference from background autofluorescence. H2S, an ‘evil and positive’ molecule, is not only toxic, but also produces significant effects; a ‘greedy’ molecule, is not only a strong nucleophile under physiological conditions, but also undergoes a continuous double nucleophilic reaction. Therefore, in this tutorial review, we will highlight recent advances made since 2015 in the development and application of red/NIR fluorescent probes based on nucleophilic reactions of H2S.

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“…Reduction-based triggers include azides, − sulfonyl azides, , nitro groups, − nitroso groups, and quinones . A wide variety of electrophilic triggers that operate via hydrogen sulfide’s nucleophilicity have been developed including aldehyde-assisted ester cleavage, aldehyde-assisted conjugate addition, aldehyde-assisted dinitrophenyl cleavage, nucleophilic aromatic substitution, , nucleophilic addition to an imine, , nitrobenzoxadiazole with amine ,− or alcohol , leaving groups, vinyl chloride substitution alone or followed by cyclization, an aryl cyanate, disulfide-assisted ester cleavage, − diselenide-assisted ester cleavage, selenenyl sulfide-assisted ester cleavage, , sulfonamide cleavage, dinitrophenyl ether cleavage, − …”

Section: Hydrogen Sulfidementioning

confidence: 99%

Reaction-Based Luminescent Probes for Reactive Sulfur, Oxygen, and Nitrogen Species: Analytical Techniques and Recent Progress

2019

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A cyanine-based colorimetric and fluorescence probe for detection of hydrogen sulfide in vivo

Cited by 39 publications

References 17 publications

Sensing and Bioimaging of the Gaseous Signaling Molecule Hydrogen Sulfide by Near-Infrared Fluorescent Probes

Sensing and Bioimaging of the Gaseous Signaling Molecule Hydrogen Sulfide by Near-Infrared Fluorescent Probes

A review: Red/near‐infrared (NIR) fluorescent probes based on nucleophilic reactions of H₂S since 2015

Reaction-Based Luminescent Probes for Reactive Sulfur, Oxygen, and Nitrogen Species: Analytical Techniques and Recent Progress

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A cyanine-based colorimetric and fluorescence probe for detection of hydrogen sulfide in vivo

Cited by 39 publications

References 17 publications

Sensing and Bioimaging of the Gaseous Signaling Molecule Hydrogen Sulfide by Near-Infrared Fluorescent Probes

Sensing and Bioimaging of the Gaseous Signaling Molecule Hydrogen Sulfide by Near-Infrared Fluorescent Probes

A review: Red/near‐infrared (NIR) fluorescent probes based on nucleophilic reactions of H2S since 2015

Reaction-Based Luminescent Probes for Reactive Sulfur, Oxygen, and Nitrogen Species: Analytical Techniques and Recent Progress

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A review: Red/near‐infrared (NIR) fluorescent probes based on nucleophilic reactions of H₂S since 2015