Design, synthesis and evaluation of a novel fluorescent probe to accurately detect H2S in hepatocytes and natural waters

Shen, Dadong; Liu, Jian; Sheng, Li; Lv, Yonghui; Guo-juan, WU; Wang, Pu; Du, Kui

doi:10.1016/j.saa.2019.117690

Cited by 24 publications

(9 citation statements)

References 52 publications

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“…Expanding to sugar ligation, Wang and Du reported the hepatocyte-targeted probe 186 (QL-Gal-N 3 ), which uses a tethered galactose to target ASGPR that are overexpressed in the liver. 258 This probe provided a 102-fold fluorescence turn-on at 521 nm upon treatment with H 2 S with good selectivity, although a minor response to Cys was observed. In addition, this probe provided a larger fluorescent response in HepG2 cells than A549 or HeLa cells, which is consistent with the increased level of ASGPR in hepatic cells.…”

Section: Azide Reduction and Intramolecular Reactionmentioning

confidence: 98%

Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species

Fosnacht,

Pluth

2024

Chem. Rev.

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Hydrogen sulfide (H 2 S) is not only a well-established toxic gas but also an important small molecule bioregulator in all kingdoms of life. In contemporary biology, H 2 S is often classified as a "gasotransmitter," meaning that it is an endogenously produced membrane permeable gas that carries out essential cellular processes. Fluorescent probes for H 2 S and related reactive sulfur species (RSS) detection provide an important cornerstone for investigating the multifaceted roles of these important small molecules in complex biological systems. A now common approach to develop such tools is to develop "activitybased probes" that couple a specific H 2 S-mediated chemical reaction to a fluorescent output. This Review covers the different types of such probes and also highlights the chemical mechanisms by which each probe type is activated by specific RSS. Common examples include reduction of oxidized nitrogen motifs, disulfide exchange, electrophilic reactions, metal precipitation, and metal coordination. In addition, we also outline complementary activity-based probes for imaging reductant-labile and sulfane sulfur species, including persulfides and polysulfides. For probes highlighted in this Review, we focus on small molecule systems with demonstrated compatibility in cellular systems or related applications. Building from breadth of reported activity-based strategies and application, we also highlight key unmet challenges and future opportunities for advancing activity-based probes for H 2 S and related RSS.

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Section: Azide Reduction and Intramolecular Reactionmentioning

confidence: 98%

Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species

Fosnacht,

Pluth

2024

Chem. Rev.

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“…Further, an economical and portable paper-based device with good reliability and sensitivity for visual monitoring and real-time online analysis of H 2 S was constructed using a smart phone having easy access color-scanning application . Shen et al reported the synthesis of a fast response (within 1 min) H 2 S probe 16 through an azide reduction mediated FL detection approach . The glycosylated quinoline fluorophore endowed the probe with good water solubility to demonstrate its prospective application for the accurate detection of H 2 S in natural water.…”

Section: Small Molecules As Fluorimetric Probesmentioning

confidence: 99%

“…Mostly HS – exists in water at pH 7.4, whereas about one-third exists as undissociated H 2 S and S 2– in appreciable concentrations above pH 10. Further, sulfate can be microbially reduced to sulfide in anaerobic water . The World Health Organization has estimated the taste and odor thresholds for H 2 S in water to be 0.05–0.1 mg L –1 , whereas the maximum allowable S 2– level in drinking water is defined as 15 μM .…”

Section: Introductionmentioning

confidence: 99%

Small Molecule Optical Probes for Detection of H₂S in Water Samples: A Review

Kulkarni,

Sunil

2024

ACS Omega

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Hydrogen sulfide (H 2 S) is closely linked to not only environmental hazards, but also it affects human health due to its toxic nature and the exposure risks associated with several occupational settings. Therefore, detection of this pollutant in water sources has garnered immense importance in the analytical research arena. Several research groups have devoted great efforts to explore the selective as well as sensitive methods to detect H 2 S concentrations in water. Recent studies describe different strategies for sensing this ubiquitous gas in real-life water samples. Though many of the designed and developed H 2 S detection approaches based on the use of organic small molecules facilitate qualitative/quantitative detection of the toxic contaminant in water, optical detection has been acknowledged as one of the best, attributed to the simple, highly sensitive, selective, and good repeatability features of the technique. Therefore, this review is an attempt to offer a general perspective of easy-to-use and fast response optical detection techniques for H 2 S, fluorimetry and colorimetry, over a wide variety of other instrumental platforms. The review affords a concise summary of the various design strategies adopted by various researchers in constructing small organic molecules as H 2 S sensors and offers insight into their mechanistic pathways. Moreover, it collates the salient aspects of optical detection techniques and highlights the future scope for prospective exploration in this field based on the limitations of the existing H 2 S probes.

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“…In recent years, the gradual development of fluorescent probes for monitoring specific biomarkers based on the study of predecessors has been improved in terms of sensitivity, 50 selectivity, 51 water solubility, 52 and permeability, 53 which makes them more effective tools for detection in cells, tissues, and organisms.…”

Section: Galactose-based Hepatocyte-targeting Fluorescent Probesmentioning

confidence: 99%

Recent research progress in galactose-based fluorescent probes for detection of biomarkers of liver diseases

Deng

et al. 2022

Chem. Commun.

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Design, synthesis and evaluation of a novel fluorescent probe to accurately detect H2S in hepatocytes and natural waters

Cited by 24 publications

References 52 publications

Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species

Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species

Small Molecule Optical Probes for Detection of H₂S in Water Samples: A Review

Recent research progress in galactose-based fluorescent probes for detection of biomarkers of liver diseases

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Design, synthesis and evaluation of a novel fluorescent probe to accurately detect H2S in hepatocytes and natural waters

Cited by 24 publications

References 52 publications

Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species

Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species

Small Molecule Optical Probes for Detection of H2S in Water Samples: A Review

Recent research progress in galactose-based fluorescent probes for detection of biomarkers of liver diseases

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Product

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Small Molecule Optical Probes for Detection of H₂S in Water Samples: A Review