New Strategy for Quantifying Biological Zinc by a Modified Zinpyr Fluorescence Sensor

Zhang, Xiaoan; Hayes, Dugan; Smith, Sarah J.; Friedle, Simone; Lippard, Stephen J.

doi:10.1021/ja807156b

Cited by 148 publications

(100 citation statements)

References 16 publications

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“…We propose a binding mode involving the three nitrogen atoms of the DPA arm and the oxygen atom on the cresol ring, which triggers the spirobenzopyran ring-opening reaction. This binding mode maintains the [N 3 O] coordination sphere of previously reported sensors, such as those in the ZP family, [30, 31] ZPP1, [32] and the recently reported ZBR probes. [33] SpiroZin1 chelates Zn 2+ tightly with an apparent dissociation constant ( K d ) of 21(1) pM (Figure SI-6).…”

Section: Resultssupporting

confidence: 74%

SpiroZin1: A Reversible and pH‐Insensitive, Reaction‐Based, Red‐Fluorescent Probe for Imaging Biological Mobile Zinc

Rivera‐Fuentes

Lippard

2014

ChemMedChem

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A reversible, reaction-based sensor for biological mobile zinc was designed, prepared, and characterized. The sensing mechanism of this probe is based on the zinc-induced, ring-opening reaction of spirobenzopyran to give a cyanine fluorophore that emits in the deep-red region of the electromagnetic spectrum. This probe is not activated by protons and operates efficiently in aqueous solution at pH 7 and high ionic strength. The mechanism of this reaction was studied by using a combination of kinetics experiments and DFT calculations. The biocompatibility of the probe was demonstrated in live HeLa cells.

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Section: Resultssupporting

confidence: 74%

SpiroZin1: A Reversible and pH‐Insensitive, Reaction‐Based, Red‐Fluorescent Probe for Imaging Biological Mobile Zinc

Rivera‐Fuentes

Lippard

2014

ChemMedChem

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“…Incorporation of strongly electron-withdrawing fluoride groups on the fluorescein scaffold afforded ZP3 (vs. chloride in ZP1), which exhibits a greater dynamic range of 7-fold (Table 1, Chang et al , 2004a). An alternative approach is to modify the zinc-binding unit, as illustrated by the pyrazine/pyridine-containing donor ligands in ZPP1 (Zhang et al , 2008; Buccella et al , 2011) and (2-picolyl)(4-picolyl)amine in ZP1B (Wong et al , 2009b). Both of these substitutions reduce the p K a of the binding pocket, giving rise to 15- and 23-fold dynamic ranges, respectively, primarily by suppression of proton-induced fluorescence emission in the metal-free form.…”

Section: A Guide To Fluorescent Zinc Probesmentioning

confidence: 99%

Illuminating Mobile Zinc with Fluorescence

Huang

Lippard

2012

Methods in Enzymology

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With the aid of chemoselective sensors, fluorescence microscopy has emerged as an indispensable tool to visualize the distribution and dynamics of various biologically important molecules in live specimens. Motivated by our interest in understanding the chemistry and biology of mobile zinc underlying its physiological and pathological roles, over the past decade our laboratory has developed an extensive library of zinc fluorescence probes. In this article, we provide essential information about our sensor toolbox in order to assist investigators interested to apply our constructs to study various aspects of mobile zinc biology. We illustrate their use with several examples of imaging both exogenous and endogenous mobile zinc in live cells and tissues using various versions of fluorescence microscopy, including confocal and two-photon microscopy.

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“…In a recent report, [41] a new cell-permeable fluorescent sensor (ZPP1) that becomes highly fluorescent (~500 nm excitation and ~540 nm emission) only after binding of two Zn(II) ions (Figure 5A) has been used to longitudinally monitor the zinc content of tissues in vivo by optical imaging. ZPP1 has been used to detect zinc levels ex vivo in urine samples of PCa patients [42] and in vivo using whole-body intravital fluorescence confocal imaging of the mouse prostate.…”

Section: Zinc Detection In Prostatementioning

confidence: 99%

Zinc as an Imaging Biomarker of Prostate Cancer

Jordan

Sherry

2017

Israel Journal of Chemistry

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Zinc has long been the focus of many biological investigations because of its essential role in biology including a catalytic role in many enzymes, a structural role in the many zinc finger proteins, and a physiological role in many secretory cell processes. Divalent zinc is known to be highly abundant in healthy prostate tissues and lower in prostate cancer (PCa). Given the need for newer diagnostic methods for detection of prostate cancer, zinc-responsive probes of various types have been considered as imaging tools for detecting tissue levels of zinc. Among them, recent zinc-responsive MRI probes show great promise for non-invasive detection of zinc ion secretion from the prostate and other tissues in vivo. In this review, we summarize the need for new diagnostic tools and demonstrate how responsive zinc probes and MRI could satisfy this unmet need.

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New Strategy for Quantifying Biological Zinc by a Modified Zinpyr Fluorescence Sensor

Cited by 148 publications

References 16 publications

SpiroZin1: A Reversible and pH‐Insensitive, Reaction‐Based, Red‐Fluorescent Probe for Imaging Biological Mobile Zinc

SpiroZin1: A Reversible and pH‐Insensitive, Reaction‐Based, Red‐Fluorescent Probe for Imaging Biological Mobile Zinc

Illuminating Mobile Zinc with Fluorescence

Zinc as an Imaging Biomarker of Prostate Cancer

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