Photo‐release of Metal Ions in Living Cells

Gwizdala, Celina; Burdette, Shawn C.

doi:10.1002/9781118682975.ch9

Cited by 6 publications

(5 citation statements)

References 167 publications

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“…A 0.5 mL solution of compound 8 (0.1 M, 0.05 mmol) was mixed with 0.5 mL of ZnCl 2 (0.1 M, 0.05 mmol) and 0.05 mL of pyridine in CH 3 OH (1 M, 0.05 mmol), and sonicated for 5 min. After cooling for 36 h at 5 °C, [Zn (8)]Cl precipitated as yellow blocks suitable for X-ray crystallographic analysis (10 mg, 46% yield). mp = >260 °C.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…In the absence of known stimuli, Zn 2+ signals could evade detection by fluorescence techniques. Tools capable of spatiotemporally controlled Zn 2+ release allow interrogation of such pathways …”

Section: Introductionmentioning

confidence: 99%

“…Tools capable of spatiotemporally controlled Zn 2+ release allow interrogation of such pathways. 8 Our group previously developed photocaged complexes for Zn 2+ inspired by the o-nitrobenzyl systems for Ca 2+ . 9 ZinCast photocages modulate concentrations by weakening a Zn 2+ − anilino nitrogen interaction; however, these complexes cannot buffer Zn 2+ at physiologically relevant concentrations.…”

Section: ■ Introductionmentioning

confidence: 99%

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Zinc Photocages with Improved Photophysical Properties and Cell Permeability Imparted by Ternary Complex Formation

et al. 2019

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Photocaged complexes have demonstrated efficacy as tools to control the availability of bioactive metals in cells to interrogate signaling pathways. We describe the synthesis of two new photocages, {bis [(2-pyridyl)methyl]amino}(9-oxo-2-xanthenyl)acetic acid (XDPAdeCage, 1) {bis[(2-pyridyl)methyl]amino}(m-nitrophenyl)acetic acid (DPAdeCage, 2), which utilize a 4-xanthone acetic acid and meta-nitrobenzyl chromophore respectively, to mediate a photodecarboxylation reaction. Both photocages strongly coordinate Zn 2+ and the binding equilibrium shifts significantly toward free Zn 2+ upon the decarboxylation of the chelator. XDPAdeCage photolyzes with quantum yield of 27% with 365 nm light, and binds Zn 2+ with 4.6 pM affinity, which decreases by over 4 orders of magnitude upon uncaging. A neutral form of [Zn(XDPAdeCage)] + can be generated in situ using the anionic bidentate ligand pyrithione, which imparts membrane impermeability to the ternary complex. Using fluorescent imaging, we have confirmed transport of Zn 2+ across lipophilic membranes; in addition, RT-PCR experiments demonstrate the photocaged complexes ability to perturb cellular processes after photolysis by showing a change in the expression levels of metallothionein and zinc transporter proteins. File list (2) download file view on ChemRxiv March_22 Manuscript.pdf (734.69 KiB) download file view on ChemRxiv March_22 SI.pdf (5.45 MiB)

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Zinc Photocages with Improved Photophysical Properties and Cell Permeability Imparted by Ternary Complex Formation

et al. 2019

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“…[3] The general concept of photoactivatable probes is that the protecting group masks the biological activity of the molecule of interest until it is cleaved through a photochemical reaction. This strategy has been applied to a very diverse range of biologically active species, including metal ions, [4,5] diatomic signaling agents (i.e. NO, CO, etc.…”

Section: Chemical To Olsmentioning

confidence: 99%

Intracellular Photoactivation and Quantification Using Fluorescence Microscopy: Chemical Tools and Imaging Approaches

Bassolino¹,

Rivera‐Fuentes²

2016

Chimia

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Recent advances in optical microscopy enable the visualization and quantification of biological processes within live cells. To a great extent, these imaging techniques remain limited by the physical properties of the chemical probes that are used as fluorescent tags, detectors and actuators. At the same time, the quantification of concentrations in the intracellular medium is not trivial, but a few approaches that employ optical microscopy have been developed. Herein, we highlight a few examples of how a combination of novel chemical probes and microscopy methods could be used to bring a much-needed quantitative dimension to the field of biological imaging.

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“…Tools capable of spatiotemporally controlled Zn 2+ release allow interrogation of such pathways. 8 In addition to new pathways, such tools also complement investigations already possible with fluorescent probes.…”

mentioning

confidence: 99%

Zinc Photocages with Improved Photophysical Properties and Cell Permeability Imparted by Ternary Complex Formation

Basa¹,

Barr²,

Oakley³

et al. 2019

Preprint

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Photocaged complexes have demonstrated efficacy as tools to control the availability of bioactive metals in cells to interrogate signaling pathways. We describe the synthesis of two new photocages, {bis[(2-pyridyl)methyl]amino}(9-oxo-2-xanthenyl)acetic acid (XDPAdeCage, 1) {bis[(2-pyridyl)methyl]amino}(m-nitrophenyl)acetic acid (DPAdeCage, 2), which utilize a 4-xanthone acetic acid and meta-nitrobenzyl chromophore respectively, to mediate a photodecarboxylation reaction. Both photocages strongly coordinate Zn2+ and the binding equilibrium shifts significantly toward free Zn2+ upon the decarboxylation of the chelator. XDPAdeCage photolyzes with quantum yield of 27% with 365 nm light, and binds Zn2+ with 4.6 pM affinity, which decreases by over 4 orders of magnitude upon uncaging. A neutral form of [Zn(XDPAdeCage)]+ can be generated in situ using the anionic bidentate ligand pyrithione, which imparts membrane impermeability to the ternary complex. Using fluorescent imaging, we have confirmed transport of Zn2+ across lipophilic membranes; in addition, RT-PCR experiments demonstrate the photocaged complexes ability to perturb cellular processes after photolysis by showing a change in the expression levels of metallothionein and zinc transporter proteins.

show abstract

Photo‐release of Metal Ions in Living Cells

Cited by 6 publications

References 167 publications

Zinc Photocages with Improved Photophysical Properties and Cell Permeability Imparted by Ternary Complex Formation

Zinc Photocages with Improved Photophysical Properties and Cell Permeability Imparted by Ternary Complex Formation

Intracellular Photoactivation and Quantification Using Fluorescence Microscopy: Chemical Tools and Imaging Approaches

Zinc Photocages with Improved Photophysical Properties and Cell Permeability Imparted by Ternary Complex Formation

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