A water soluble and fast response fluorescent turn-on copper complex probe for H2S detection in zebra fish

Palanisamy, Subramanian; Lee, Lu Ying; Wang, Yu Liang; Chen, Yu-Jen; Chen, Chiao Yun; Wang, Yun-Ming

doi:10.1016/j.talanta.2015.10.019

Cited by 49 publications

(20 citation statements)

References 30 publications

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“…[177] The methylanthracene triazole-tetraazacyclododecane 150 can form a complex with Cu(II) ions which quenches the ligand fluorescence (λmax = 415 and 435 nm). [178] The photochromic triazole-conjugated spiropyran 151 changes colour upon Cu(II) complexation, showing a new absorption peak at 571 nm. [179] The amino acid functionalised bis-triazolyl hexose derivative 152 efficiently detects Cu(II)/cyanide by quenching/switch-on of the ligand emission (λmax = 375 nm).…”

Section: Triazole-based Sensors For Metal Ionsmentioning

confidence: 99%

Photophysics and photochemistry of 1,2,3-triazole-based complexes

Scattergood

Sinopoli

Elliott

2017

Coordination Chemistry Reviews

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The copper-catalysed cycloaddition of alkynes and azides to form 1,2,3-triazoles has emerged as a powerful tool in ligand design and the synthesis of novel transition metal complexes. In this review we focus on the photophysical properties of metal complexes bearing 1,2,3-triazole-based ligands with a particular emphasis on those of d 6 metals including rhenium(I), iron(II), ruthenium(II), osmium(II) and iridium(III). We also highlight key examples of triazole complexes of platinum(II) and palladium(II) as well as the lanthanides and coinage metals. 1. Introduction 2. Photophysical properties of d 6 metal triazole-based complexes 2.1 Rhenium(I) complexes 2.2 Iridium(III) complexes 2.3 Ruthenium(II) complexes 2.4 Iron(II) complexes 2.5 Osmium(II) complexes 2.6 Photochemistry of 1,2,3-triazole-based d 6 metal complexes 3. Platinum(II) and palladium(II) complexes 4. Coinage metal complexes 5. Lanthanide complexes 6. Triazole-based sensors for metal ions 7. Conclusions & outlook.

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Section: Triazole-based Sensors For Metal Ionsmentioning

confidence: 99%

Photophysics and photochemistry of 1,2,3-triazole-based complexes

Scattergood

Sinopoli

Elliott

2017

Coordination Chemistry Reviews

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“…The majority of the copper complexes reported in the literature as H 2 S sensors harness the displacement of the metal from the fluorophores' environment to generally produce fluorescence turn‐on changes by the H 2 S‐mediated precipitation of metal sulfides , , , , , , . In contrast, in 2015, our research group reported a simple copper porphyrin complex as a “turn‐on” fluorescent probe for the detection of H 2 S in aqueous media, in which the sensing mechanism was based on binding HS – to the copper center …”

Section: Resultsmentioning

confidence: 97%

“…Indeed, Cu 2+ is a transition metal with an incompletely filled d shell, which makes possible the quenching of the fluorophore fluorescence by energy or electron transfer between the d orbitals of the metal ion and the excited states of the fluorophore . It is also well known that sulfide reacts with copper complexes, yielding a very stable CuS species (with a low solubility‐product constant, K sp = 1.27 × 10 –36 ) , . 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.…”

Section: Introductionmentioning

confidence: 99%

“…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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“…Based on a similar strategy, Zhao and Song demonstrated a series of probes with para-azidobenzyl group attached to the 1,8-naphthalimide [ 36 , 37 ]. Other methods are based on unique dual nucleophilic reactions [ 25 , 38 , 39 ], high binding affinity towards copper ions [ 40 , 41 , 42 ] and a specific addition reaction to unsaturated double bond [ 43 , 44 , 45 ].…”

Section: Resultsmentioning

confidence: 99%

Salivary Hydrogen Sulfide Measured with a New Highly Sensitive Self-Immolative Coumarin-Based Fluorescent Probe

et al. 2018

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Ample evidence suggests that H2S is an important biological mediator, produced by endogenous enzymes and microbiota. So far, several techniques including colorimetric methods, electrochemical analysis and sulfide precipitation have been developed for H2S detection. These methods provide sensitive detection, however, they are destructive for tissues and require tedious sequences of preparation steps for the analyzed samples. Here, we report synthesis of a new fluorescent probe for H2S detection, 4-methyl-2-oxo-2H-chromen-7-yl 5-azidopentanoate (1). The design of 1 is based on combination of two strategies for H2S detection, i.e., reduction of an azido group to an amine in the presence of H2S and intramolecular lactamization. Finally, we measured salivary H2S concentration in healthy, 18–40-year-old volunteers immediately after obtaining specimens. The newly developed self-immolative coumarin-based fluorescence probe (C15H15N3O4) showed high sensitivity to H2S detection in both sodium phosphate buffer at physiological pH and in saliva. Salivary H2S concentration in healthy volunteers was within a range of 1.641–7.124 μM.

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A water soluble and fast response fluorescent turn-on copper complex probe for H2S detection in zebra fish

Cited by 49 publications

References 30 publications

Photophysics and photochemistry of 1,2,3-triazole-based complexes

Photophysics and photochemistry of 1,2,3-triazole-based complexes

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

Salivary Hydrogen Sulfide Measured with a New Highly Sensitive Self-Immolative Coumarin-Based Fluorescent Probe

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A water soluble and fast response fluorescent turn-on copper complex probe for H2S detection in zebra fish

Cited by 49 publications

References 30 publications

Photophysics and photochemistry of 1,2,3-triazole-based complexes

Photophysics and photochemistry of 1,2,3-triazole-based complexes

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

Salivary Hydrogen Sulfide Measured with a New Highly Sensitive Self-Immolative Coumarin-Based Fluorescent Probe

Contact Info

Product

Resources

About

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