Complexation of zinc(II) and other divalent metal ions by the fluorophore 2-methyl-8-(toluene-p-sulfonamido)-6-quinolyloxyacetic acid in 50% aqueous ethanol

Hendrickson, Kym M.; Rodopoulos, Theo; Pittet, Pierre-André; Mahadevan, I. B.; Lincoln, Stephen F.; Ward, A. D.; Kurucsev, Tomas; Duckworth, Paul A.; Forbes, Ian J.; Zalewski, Peter D.; Betts, W H

doi:10.1039/a703433d

Cited by 37 publications

(29 citation statements)

References 24 publications

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“…3). Our conclusion is similar to that of Hendrickson et al (1997) who found that Zinquin predominantly forms a 1:2 complex with traces of 1:1 in 50% aqueous ethanol solution. Fahrni and O'Halloran (1999) found no evidence for 1:1 complexes in potentiometric titrations performed in an 80:20 mixture of DMSO and water; however, their experiments were performed at 1:2 ratio of Zn 2ϩ and Zinquin, which would tend to minimize the formation of the 1:1 complex.…”

Section: Characteristics Of Zinquin and Tflzn In Aqueous Solutionsupporting

confidence: 92%

Fluorescent Detection of Zn2+-Rich Vesicles with Zinquin: Mechanism of Action in Lipid Environments

Snitsarev

Budde

Stricker

et al. 2001

Biophysical Journal

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High concentrations of free Zn2+ ions are found in certain glutamatergic synaptic vesicles in the mammalian brain. These terminals can be visualized histochemically with quinoline sulfonamide compounds that form fluorescent complexes with Zn2+. The present study was undertaken to examine the interaction of the water-soluble quinoline sulfonamide probe, Zinquin (2-methyl-8-(toluene-p-sulfonamido)-6-quinolyloxyacetic acid) with the complex heterogeneous cellular environment. Experiments on rat hippocampal and neocortical slices gave indications that Zinquin in its free acid form was able to diffuse across the plasma and synaptic vesicle membranes. Further experiments were undertaken on unilamellar liposomes to study the interaction of Zinquin and its metal complexes in membranes. These experiments confirmed that Zinquin is able to diffuse across lipid bilayers. Steady-state and time-resolved fluorimetric studies showed that Zinquin in aqueous solution mainly forms a 1:2 (metal:ligand) complex with small amounts of a 1:1 complex. Formation of the 1:1 complex was favored by the presence of lipid, suggesting that it partitions into membranes. Evidence is presented that Zinquin can act as a Zn(2+)-ionophore, exchanging Zn2+ for two protons. The presence of a pH gradient across vesicles traps the Zn(2+)-probe complex within the vesicles. Zinquin is useful as a qualitative probe for detecting the presence of vesicular Zn2+; however, its tendency to partition into membranes and to serve as an ionophore should be borne in mind.

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Section: Characteristics Of Zinquin and Tflzn In Aqueous Solutionsupporting

confidence: 92%

Fluorescent Detection of Zn2+-Rich Vesicles with Zinquin: Mechanism of Action in Lipid Environments

Snitsarev

Budde

Stricker

et al. 2001

Biophysical Journal

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“…, which may be due to nonradiative energy transitions or energy transfer between the d orbital of the ions and the fluorophore. [14] These results demonstrate the high selectivity of L1 towards Zn 2+ . For practical applications, the sensing ability of L1 towards Zn 2+ at different pH values was investigated (Figure 6).…”

Section: When Znmentioning

confidence: 66%

A Highly Selective Fluorescent and Colorimetric Chemosensor for Zn^II and Its Application in Cell Imaging

et al. 2011

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“…However, the fluorescence of the L1/Zn 2+ system was quenched by Cu 2+ and Hg 2+ , which may be due to nonradiative energy transition in the process of electron or energy transfer between the d orbital of the ions and the fluorophore. [7,18] Figure 5). L1 shows no appreciable fluorescence response to Zn 2+ in an acidic environment because protonation of the amino group of L1 weakens the coordination ability of Zn 2+ .…”

Section: Resultsmentioning

confidence: 99%

A Highly Zinc(II)‐Selective Fluorescent Sensor Based on 8‐Aminoquinoline and Its Application in Biological Imaging

Xie

Wang

et al. 2011

Eur J Inorg Chem

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Complexation of zinc(II) and other divalent metal ions by the fluorophore 2-methyl-8-(toluene-p-sulfonamido)-6-quinolyloxyacetic acid in 50% aqueous ethanol

Cited by 37 publications

References 24 publications

Fluorescent Detection of Zn2+-Rich Vesicles with Zinquin: Mechanism of Action in Lipid Environments

Fluorescent Detection of Zn2+-Rich Vesicles with Zinquin: Mechanism of Action in Lipid Environments

A Highly Selective Fluorescent and Colorimetric Chemosensor for Zn^II and Its Application in Cell Imaging

A Highly Zinc(II)‐Selective Fluorescent Sensor Based on 8‐Aminoquinoline and Its Application in Biological Imaging

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Complexation of zinc(II) and other divalent metal ions by the fluorophore 2-methyl-8-(toluene-p-sulfonamido)-6-quinolyloxyacetic acid in 50% aqueous ethanol

Cited by 37 publications

References 24 publications

Fluorescent Detection of Zn2+-Rich Vesicles with Zinquin: Mechanism of Action in Lipid Environments

Fluorescent Detection of Zn2+-Rich Vesicles with Zinquin: Mechanism of Action in Lipid Environments

A Highly Selective Fluorescent and Colorimetric Chemosensor for ZnII and Its Application in Cell Imaging

A Highly Zinc(II)‐Selective Fluorescent Sensor Based on 8‐Aminoquinoline and Its Application in Biological Imaging

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A Highly Selective Fluorescent and Colorimetric Chemosensor for Zn^II and Its Application in Cell Imaging