Design and synthesis of a Cu(II)-complex-based carbazole-hemicyanine hybrid for fluorescent sensing of H 2 S in SDS micellar solution

Xu, Qian; Gu, Zhen-yuan; Xing, Guo‐wen

doi:10.1016/j.tet.2017.02.060

Cited by 17 publications

(8 citation statements)

References 87 publications

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“…The behavior of py‐cyclam‐pyr‐Cu in the presence of NaSH is thus very similar to that reported for several related Cu 2+ complexes , …”

Section: Resultssupporting

confidence: 85%

“…By harnessing these two favorable conditions, in the past few years, several examples of copper complexes have been reported as efficient fluorescent H 2 S sensors. Their working principle exploits copper‐mediated precipitation of sulfide, with subsequent release of the organic ligand, which restores the initial fluorescence intensity of the free ligand , , , , …”

Section: Introductionmentioning

confidence: 99%

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A Cyclam‐Based Fluorescent Ligand as a Molecular Beacon for Cu²⁺ and H₂S Detection

2017

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A pentadentate cage‐like cyclam‐based fluorescent ligand has been designed, synthesized, and characterized by 1D and 2D NMR spectroscopic analysis. To further characterize the title ligand, ESI‐MS, UV/Vis spectroscopy, and fluorescence experiments have been also performed. Its suitability as a chemosensor for the detection of Cu2+ ions has been successfully explored with a variety of spectroscopic techniques (i.e., ESI‐MS, UV/Vis, and fluorescence). A Job's plot experiment, together with ESI‐MS experiments, indicate a 1:1 stoichiometry for the binding of Cu2+ to the cyclam‐based ligand. Fluorescence experiments corroborate this hypothesis. The resulting system is selective in the recognition of copper and is stable for a week, as assessed by fluorescence spectroscopy. The CuII complex has been isolated and tested as a fluorescent probe for the detection of H2S. NMR spectroscopy and ESI‐MS investigations have provided evidence that H2S recognition occurs through a copper‐displacement mechanism, as reported in the literature for different copper complexes. The system functions with a selective response to HS–, harnessing a concentration‐dependent “turn‐on” of the initial fluorescence intensity.

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“…The behavior of py‐cyclam‐pyr‐Cu in the presence of NaSH is thus very similar to that reported for several related Cu 2+ complexes , …”

Section: Resultssupporting

confidence: 85%

Section: Introductionmentioning

confidence: 99%

A Cyclam‐Based Fluorescent Ligand as a Molecular Beacon for Cu²⁺ and H₂S Detection

2017

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“…This probe was also used to image exogenous H 2 S in HeLa cells. Adding an extra pyridyl binding motif, Xing reported the tri(2-pyridylmethyl)ethylenediamine (TPEA) carbazole-hemicyanine construct 806 (HACBA), which provided a fluorescent response to H 2 S in buffer with 5 mM SDS, but also had a minor response to Cys and GSH . Wang reported a dansyl conjugate 807 (DNS-Cu), which provided a turn-on response to H 2 S and good selectivity over competing anions and was used to investigate H 2 S in different water samples …”

Section: Metal-based 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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“…This sensor was continuously exposed to 200 ppb H 2 S 5 times at room temperature, and showed good repeatability after continuous adsorption and desorption process. In 2017, Xu et al [ 45 ] designed and synthesized a novel fluorescent chemical sensor HACBA-Cu 2+ with carbazole-hemicyanine fluorophore as signal reporter and N , N , N ’-tri(2-pyridylmethyl)ethylenediamin e (TPEA) as binding site. Alternately, added H 2 S and Cu 2+ can achieve an “on-off-on” form of fluorescence cycle, and at least 3 repeat cycles were observed, but the fluorescence intensity decreased after multiple repeats.…”

Section: Metal Affinity Based H 2 S Detectionmentioning

confidence: 99%

Review of Chemical Sensors for Hydrogen Sulfide Detection in Organisms and Living Cells

Yang

Zhou

Wang

et al. 2023

Sensors

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As the third gasotransmitter, hydrogen sulfide (H2S) is involved in a variety of physiological and pathological processes wherein abnormal levels of H2S indicate various diseases. Therefore, an efficient and reliable monitoring of H2S concentration in organisms and living cells is of great significance. Of diverse detection technologies, electrochemical sensors possess the unique advantages of miniaturization, fast detection, and high sensitivity, while the fluorescent and colorimetric ones exhibit exclusive visualization. All these chemical sensors are expected to be leveraged for H2S detection in organisms and living cells, thus offering promising options for wearable devices. In this paper, the chemical sensors used to detect H2S in the last 10 years are reviewed based on the different properties (metal affinity, reducibility, and nucleophilicity) of H2S, simultaneously summarizing the detection materials, methods, linear range, detection limits, selectivity, etc. Meanwhile, the existing problems of such sensors and possible solutions are put forward. This review indicates that these types of chemical sensors competently serve as specific, accurate, highly selective, and sensitive sensor platforms for H2S detection in organisms and living cells.

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Design and synthesis of a Cu(II)-complex-based carbazole-hemicyanine hybrid for fluorescent sensing of H 2 S in SDS micellar solution

Cited by 17 publications

References 87 publications

A Cyclam‐Based Fluorescent Ligand as a Molecular Beacon for Cu²⁺ and H₂S Detection

A Cyclam‐Based Fluorescent Ligand as a Molecular Beacon for Cu²⁺ and H₂S Detection

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

Review of Chemical Sensors for Hydrogen Sulfide Detection in Organisms and Living Cells

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Design and synthesis of a Cu(II)-complex-based carbazole-hemicyanine hybrid for fluorescent sensing of H 2 S in SDS micellar solution

Cited by 17 publications

References 87 publications

A Cyclam‐Based Fluorescent Ligand as a Molecular Beacon for Cu2+ and H2S Detection

A Cyclam‐Based Fluorescent Ligand as a Molecular Beacon for Cu2+ and H2S Detection

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

Review of Chemical Sensors for Hydrogen Sulfide Detection in Organisms and Living Cells

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Product

Resources

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A Cyclam‐Based Fluorescent Ligand as a Molecular Beacon for Cu²⁺ and H₂S Detection

A Cyclam‐Based Fluorescent Ligand as a Molecular Beacon for Cu²⁺ and H₂S Detection