A BODIPY-based fluorescent chemosensor with 2, 6-substitution for visual and highly selective detection of S2–

Wu, Jianwei; Chan, Chenming; Li, Jia; Shi, Yaqiao; Xue, Zhaoli; Zhao, Long

doi:10.1016/j.saa.2023.122741

Cited by 6 publications

(2 citation statements)

References 39 publications

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“…Jiang reported a related construct in 314, which reacts with H 2 S to generate a turn-off response at 615 nm with good selectivity over 10 μM Cys, Hcy, and GSH. 349 350 Expanding to other fluorophores, Cui and Xu also reported an early example of this approach in 2013 by appending the DNP group to the naphthalimide platform to report 316 (NI-NHS) (Figure 73). 351 This probe showed moderate selectivity over thiols in 10% MeCN in buffer and was used to image exogenous H 2 S in MCF-7 cells using two-photon excitation at 810 nm.…”

Section: Electrophilic H 2 S Probesmentioning

confidence: 99%

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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 H 2 S Probesmentioning

confidence: 99%

“…This turn-off response was confirmed with exogenous H 2 S in HCT-116 and CT-26 cells. Adding a second DNP motif, Xue and Zhao reported 315 (LM-BDP), which generated a turn-off response to H 2 S at 558 nm in 80% MeCN in buffer and also responded to exogenous H 2 S in Raw 264.7 cells …”

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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Blue‐to‐Red‐Emissive Star‐Shaped Boranils

Bai,

Nipate,

Malakalapalli

2023

ChemistrySelect

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Intriguing luminescent properties of boranil complexes have gained a prominence. Here, we report the synthesis and optical properties of star‐shaped boranil complexes. The strategy involves one‐step synthesis by a simple mixing triformylphloroglucinol with various aromatic amines in the presence of diisopropylethyl amine (DIPEA), and the complexing reagent of BF3⋅Et2O in chloroform at 80 °C for 24 hours. The complexes are obtained in good yields (60–85 %). These boranil complexes have strong fluorescence in both solution (λmax=466–605 nm) and solid (λmax=612–659 nm) states, with the fluorescence quantum yields varying from 1.5–57 % in chloroform. The emission color of the complexes has been tuned from blue to red by varying the aryl‐substituents in the complexes. Further understanding of the optical and electronic properties is obtained theoretically using DFT computations.

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Highly selective dual-responsive chemosensor for S2- in pure water and its application to environmental samples such as beverage, zebrafish and food spoilage

Jung,

Lee,

Jin

et al. 2024

Journal of Environmental Chemical Engineering

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A BODIPY-based fluorescent chemosensor with 2, 6-substitution for visual and highly selective detection of S2–

Cited by 6 publications

References 39 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

Blue‐to‐Red‐Emissive Star‐Shaped Boranils

Highly selective dual-responsive chemosensor for S2- in pure water and its application to environmental samples such as beverage, zebrafish and food spoilage

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