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Zinc Photocages with Improved Photophysical Properties and Cell Permeability Imparted by Ternary Complex Formation.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2019 Jul 31; Vol. 141 (30), pp. 12100-12108. Date of Electronic Publication: 2019 Jul 16. - Publication Year :
- 2019
-
Abstract
- Photocaged complexes can control the availability of metal ions to interrogate cellular signaling pathways. We describe a new photocage, {bis[(2-pyridyl)methyl]amino}(9-oxo-2-xanthenyl)acetic acid (XDPAdeCage, 1 ), which utilizes a 2-xanthone acetic acid group to mediate a photodecarboxylation reaction. XDPAdeCage photolyzes with a quantum yield of 27%, and binds Zn <superscript>2+</superscript> with 4.6 pM affinity, which decreases by over 4 orders of magnitude after photolysis. For comparison to our previous approach to Zn <superscript>2+</superscript> release via photodecarboxylation, the analogous photocage {bis[(2-pyridyl)methyl]amino}( m -nitrophenyl)acetic acid (DPAdeCage, 2 ), which uses a m -nitrobenzyl chromophore, was also prepared and characterized. The advantages of the 2-xanthone acetic acid chromophore include red-shifted excitation and a higher extinction coefficient at the preferred uncaging wavelength. The neutral ternary complex of [Zn(XDPAdeCage)] <superscript>+</superscript> with the anionic ligand pyrithione is membrane permeable, which circumvents the need to utilize invasive techniques to introduce intracellular Zn <superscript>2+</superscript> fluctuations. Using fluorescent imaging, we have confirmed transport of Zn <superscript>2+</superscript> across membranes; in addition, RT-PCR experiments demonstrate changes in expression of Zn <superscript>2+</superscript> -responsive proteins after photolysis.
- Subjects :
- Acetic Acid chemistry
Cell Membrane chemistry
Cell Membrane metabolism
Cells, Cultured
Coordination Complexes chemistry
Fibroblasts chemistry
Fluorescent Dyes chemistry
Humans
Molecular Structure
Optical Imaging
Permeability
Photochemical Processes
Photolysis
Xanthones chemistry
Zinc chemistry
Acetic Acid metabolism
Coordination Complexes metabolism
Fibroblasts metabolism
Fluorescent Dyes metabolism
Xanthones metabolism
Zinc metabolism
Subjects
Details
- Language :
- English
- ISSN :
- 1520-5126
- Volume :
- 141
- Issue :
- 30
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 31256585
- Full Text :
- https://doi.org/10.1021/jacs.9b05504