A cancer cell-specific benzoxadiazole-based fluorescent probe for hydrogen sulfide detection in mitochondria

Fortibui, Maxine Mambo; Yoon, Dae Wui; Lim, Joong Yeon; Lee, SoHyun; Choi, Min-Sun; Heo, June Seok; Kim, Jinkwan; Kim, Jinheung

doi:10.1039/d0dt03653f

Cited by 11 publications

(5 citation statements)

References 52 publications

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“… This discrimination for Cys/Hcy and GSH/H 2 S was also demonstrated in HeLa cells and larval zebrafish. Kim and Kim reported 552 , which reacts with H 2 S to generate a fluorescent response at 545 nm and was reported to be selective for H 2 S over other analytes including Cys . This probe was used to image different H 2 S levels in H9C2 as well as cancerous cell lines HUH7, MDA231, and U87MG.…”

Section: Electrophilic H2s Probesmentioning

confidence: 99%

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: Electrophilic H2s Probesmentioning

confidence: 99%

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

Fosnacht,

Pluth

2024

Chem. Rev.

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“…There are many kinds of H 2 S probes which have been designed and synthesized to date [ 57 , 58 , 59 ]. In the subsequent sections, we summarize two different mechanisms of H 2 S detection reported over the last 7 years [ 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 ].…”

Section: Different Mechanisms Of H 2 S Detectionmentioning

confidence: 99%

H2S Sensors: Synthesis, Optical Properties, and Selected Biomedical Applications under Visible and NIR Light

2023

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Hydrogen sulfide (H2S) is an essential signaling gas within the cell, and its endogenous levels are correlated with various health diseases such as Alzheimer’s disease, diabetes, Down’s syndrome, and cardiovascular disease. Because it plays such diverse biological functions, being able to detect H2S quickly and accurately in vivo is an area of heightened scientific interest. Using probes that fluoresce in the near-infrared (NIR) region is an effective and convenient method of detecting H2S. This approach allows for compounds of high sensitivity and selectivity to be developed while minimizing cytotoxicity. Herein, we report a review on the synthesis, mechanisms, optical properties, and selected biomedical applications of H2S sensors.

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“…Moreover, treatment with NaHS suppressed the anti-apoptotic markers in B-cell lymphoma 2 (Bcl-2) by regulating the p53 and p38 MAPK pathways (Pan et al, 2014;Zhao et al, 2015), thus promoting cancer cell apoptosis (Zuhra et al, 2020b;Xia et al, 2021). Moreover, H 2 S acts as a stimulator of mitochondrial electron transfer, and endogenous H 2 S stimulates adenosine triphosphate (ATP) production in cancer cells, which plays an important role in preventing mitochondrial fission and maintaining mitochondrial DNA repair (Fortibui et al, 2021).…”

Section: The Effect Of H 2 S In Hepatocellular Carcinomamentioning

confidence: 99%

“…Endogenous and exogenous H 2 S play different roles in HCC through different mechanisms. (A) Endogenous H 2 S promotes immune escape and proliferation and enhances drug resistance in HCC, which may be related to the promotion of Treg-mediated immune evasion (Xu et al, 2021;Zhou et al, 2021), the stimulation of ATP production (Fortibui et al, 2021), and the activation of the STAT3/Akt/Bcl-2 pathway (Wang et al, 2018). The inhibition of reactive oxygen species (ROS) (Wang et al, 2018).…”

Section: Figurementioning

confidence: 99%

The double-edged role of hydrogen sulfide in the pathomechanism of multiple liver diseases

Liu

Wang

et al. 2022

Front. Pharmacol.

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In mammalian systems, hydrogen sulfide (H2S)—one of the three known gaseous signaling molecules in mammals—has been found to have a variety of physiological functions. Existing studies have demonstrated that endogenous H2S is produced through enzymatic and non-enzymatic pathways. The liver is the body’s largest solid organ and is essential for H2S synthesis and elimination. Mounting evidence suggests H2S has essential roles in various aspects of liver physiological processes and pathological conditions, such as hepatic lipid metabolism, liver fibrosis, liver ischemia‒reperfusion injury, hepatocellular carcinoma, hepatotoxicity, and acute liver failure. In this review, we discuss the functions and underlying molecular mechanisms of H2S in multiple liver pathophysiological conditions.

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A cancer cell-specific benzoxadiazole-based fluorescent probe for hydrogen sulfide detection in mitochondria

Abstract: A cancer cell specific fluorescent probe is reported for sensing hydrogen sulfide.

Cited by 11 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

H2S Sensors: Synthesis, Optical Properties, and Selected Biomedical Applications under Visible and NIR Light

The double-edged role of hydrogen sulfide in the pathomechanism of multiple liver diseases

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