Molecular engineering of benzenesulfonyl analogs for visual hydrogen polysulfide fluorescent probes based on Nile red skeleton

Qian, Feng; Song, Yoonho; Ma, Youjie; Yan, Deyue; Xu, Pengyue; Sheng, Kangjia; Zhang, Yongmin; Li, Jianli; Wu, Shaoping

doi:10.1016/j.saa.2023.122658

Cited by 8 publications

(4 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“… They observed that higher electrophilicity resulted in faster reactivity with RSS, with 2-nitrobenzenesulfonyl based 1018 showing the highest selectivity and response for H 2 S n over thiols and H 2 S. This probe was subsequently used to image exogenous H 2 S n in HeLa cells. Song and Wu also developed a variety of electronically substituted H 2 S probes, with 1027 (NR-BS4) being the most sensitive and selective, responding to H 2 S n with a fluorescence turn-on at 590 nm with good selectivity for H 2 S n over anions, H 2 S, and thiols, although NaClO did decrease the sensitivity of the probe . The probe was further used to image exogenous H 2 S n , LPS-induced H 2 S n , and PAG treatment in HepG2 cells and exogenous H 2 S n in larval zebrafish.…”

Section: Fluorescent Probes For Sulfane Sulfur Containing Speciesmentioning

confidence: 99%

“…Song and Wu also developed a variety of electronically substituted H 2 S probes, with 1027 (NR-BS4) being the most sensitive and selective, responding to H 2 S n with a fluorescence turn-on at 590 nm with good selectivity for H 2 S n over anions, H 2 S, and thiols, although NaClO did decrease the sensitivity of the probe. 1013 The probe was further used to image exogenous H 2 S n , LPS-induced H 2 S n , and PAG treatment in HepG2 cells and exogenous H 2 S n in larval zebrafish.…”

Section: Electrophilic Probesmentioning

confidence: 99%

See 1 more Smart Citation

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

Fosnacht,

Pluth

2024

Chem. Rev.

View full text Add to dashboard Cite

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.

show abstract

Section: Fluorescent Probes For Sulfane Sulfur Containing Speciesmentioning

confidence: 99%

Section: Electrophilic Probesmentioning

confidence: 99%

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

Fosnacht,

Pluth

2024

Chem. Rev.

View full text Add to dashboard Cite

show abstract

“…Nowadays, the methods of detecting biothiols are diversified and gradually improved. Yet, different detection methods have their own advantages and drawbacks [2,[4][5][6][7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Theoretical Investigation of a Coumarin Fluorescent Probe for Distinguishing the Detection of Small-Molecule Biothiols

Deng,

Huang,

Feng

et al. 2024

Molecules

View full text Add to dashboard Cite

Monitoring the level of biothiols in organisms would be beneficial for health inspections. Recently, 3-(2′-nitro vinyl)-4-phenylselenyl coumarin as a fluorescent probe for distinguishing the detection of the small-molecule biothiols cysteine/homocysteine (Cys/Hcy) and glutathione (GSH) was developed. By introducing 4-phenyselenium as the active site, the probe CouSeNO2/CouSNO2 was capable of detecting Cys/Hcy and GSH in dual fluorescence channels. Theoretical insights into the fluorescence sensing mechanism of the probe were provided in this work. The details of the electron excitation process in the probe and sensing products under optical excitation and the fluorescent character were analyzed using the quantum mechanical method. All these theoretical results would provide insight and pave the way for the molecular design of fluorescent probes for the detection of biothiols.

show abstract

“…15 In addition to its lethal effects, H 2 S also modulates a wide range of physiological actions including vasodilation, anti-inflammatory effects, insulin release, neurotransmission, antioxidant properties, anti-apoptotic effects, and neuroprotection. 16 Notably, H 2 S triggers S -sulfhydration of Keap1, activating Nrf 2 and facilitating its nuclear translocation, which results in the production of antioxidant proteins. 17 Numerous studies have demonstrated that H 2 S ranks as the third most crucial signaling molecule in organisms following CO and NO.…”

Section: Introductionmentioning

confidence: 99%

A novel fluorescent probe with a phosphofluorene molecular structure for selective detection of hydrogen sulfide in living cells

Zhang,

Liu,

Chen

et al. 2024

RSC Adv.

View full text Add to dashboard Cite

show abstract

Molecular engineering of benzenesulfonyl analogs for visual hydrogen polysulfide fluorescent probes based on Nile red skeleton

Cited by 8 publications

References 28 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

Theoretical Investigation of a Coumarin Fluorescent Probe for Distinguishing the Detection of Small-Molecule Biothiols

A novel fluorescent probe with a phosphofluorene molecular structure for selective detection of hydrogen sulfide in living cells

Contact Info

Product

Resources

About