A near-infrared fluorescent probe based on nucleophilic substitution–cyclization for selective detection of hydrogen sulfide and bioimaging

Men, Jinxia; Yang, Xiaojun; Zhang, Huibin; Zhou, Jinpei

doi:10.1016/j.dyepig.2017.12.036

Cited by 54 publications

(24 citation statements)

References 36 publications

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“…Disulfide-linked receptor 33 (see Chart ), based on 2-(pyridin-2-yl-disulfanyl)benzoic acid attached to dicyanomethylene-4 H -pyran (DCM), was reported for H 2 S detection . The probe 33 was selective for H 2 S, among other biothiols with a LOD of 1.1 nM.…”

Section: Small-molecule-based Nir Probesmentioning

confidence: 99%

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%

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

et al. 2020

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“…Men et al . reported a fluorescent probe 30 (Figure 17) based on nucleophilic substitution–cyclization for H 2 S. [ 108 ] Probe 30 displayed excellent sensitivity and selectivity toward H 2 S over other relevant analytes including ions, ROS, and biothiols under physiological conditions. It was able to detect H 2 S rapidly with significant NIR fluorescent turn‐on responses around 680 nm with a visual colour change from light yellow to pink in DMSO–PBS solution (10 mM, pH = 7.4, 1/1, v /v).…”

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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“…Fluorescence technology is particularly promising for such purposes, as it enables monitoring of the target with superior temporal and spatial resolution [56,57,58,59], especially for in vivo applications. By exploiting its unique characteristics, such as strong nucleophilicity and ability to reduce potency, various small-molecule fluorescent probes have been developed for detecting and imaging H 2 S. These probes can be mainly categorized into three types according to their sensing strategy: (i) sensors based on the H 2 S-mediated reduction of an azide/nitro group to the amine [60,61,62,63]; (ii) sensors based on the H 2 S-participated nucleophilic reaction [64,65,66,67]; and (iii) sensors based on the binding reaction between sulfide and Cu 2+ [68,69]. By exploiting the similar sensing strategies and carefully employing post-synthetic modification approaches, a number of MOF-based fluorescent H 2 S probes (Table 1) were successfully constructed in the last few years [70].…”

Section: Mof-based Luminescent Chemodosimeters For Sulfur Compoundsmentioning

confidence: 99%

Recent Progress in Metal–Organic Framework (MOF) Based Luminescent Chemodosimeters

et al. 2019

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Metal–organic frameworks (MOFs), as a class of crystalline hybrid architectures, consist of metal ions and organic ligands and have displayed great potential in luminescent sensing applications due to their tunable structures and unique photophysical properties. Until now, many studies have been reported on the development of MOF-based luminescent sensors, which can be classified into two major categories: MOF chemosensors based on reversible host–guest interactions and MOF chemodosimeters based on the irreversible reactions between targets with a probe. In this review, we summarize the recently developed luminescent MOF-based chemodosimeters for various analytes, including H2S, HClO, biothiols, fluoride ions, redox-active biomolecules, Hg2+, and CN−. In addition, some remaining challenges and future perspectives in this area are also discussed.

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A near-infrared fluorescent probe based on nucleophilic substitution–cyclization for selective detection of hydrogen sulfide and bioimaging

Cited by 54 publications

References 36 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

Recent Progress in Metal–Organic Framework (MOF) Based Luminescent Chemodosimeters

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A near-infrared fluorescent probe based on nucleophilic substitution–cyclization for selective detection of hydrogen sulfide and bioimaging

Cited by 54 publications

References 36 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

Recent Progress in Metal–Organic Framework (MOF) Based Luminescent Chemodosimeters

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