ArticleJournal of the American Chemical Society2005
QZ1 and QZ2: rapid, reversible quinoline-derivatized fluoresceins for sensing biological Zn(II).
Article in Journal of the American Chemical Society, 2005. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 44 papers.
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Who cites it
44 citing papers in PubMed.
- Rosamine derivatives ofOrganic & biomolecular chemistry · 2026Article
- Bright Zinc Probes with Thiomorpholine Monoxide Auxochromes for Imaging Insulin Secretion.Chemical & biomedical imaging · 2025Article
- A Review on Small Molecule Based Fluorescence Chemosensors for Bioimaging Applications.Journal of fluorescence · 2025Review
- Mechanistic Innovations in Fluorescent Chemosensors for Detecting Toxic Ions: PET, ICT, ESIPT, FRET and AIE Approaches.Journal of fluorescence · 2025Review
- Targeted imaging of lysosomal zinc ions with a tetrahedral DNA framework fluorescent reporter.National science review · 2024Article
- Rational design of a genetically encoded NMR zinc sensor.Chemical science · 2023Article
- Mobile zinc as a modulator of sensory perception.FEBS letters · 2023Review
- Unusual Reactivity and Metal Affinity of Water-Soluble Dipyrrins.Inorganic chemistry · 2022Article
- Non-invasive radionuclide imaging of trace metal trafficking in health and disease: "PET metallomics".RSC chemical biology · 2022Review
- ZnRSC advances · 2021Article
- Fast Ion-Chelate Dissociation Rate forJournal of the American Chemical Society · 2021Article
- Thermally Stable Fluorogenic Zn(II) Sensor Based on a Bis(benzimidazole)pyridine-Linked Phenyl-Silsesquioxane Polymer.ACS omega · 2020Article
- Solid-State Emissive Metallo-Supramolecular Assemblies of Quinoline-Based Acyl Hydrazone.Sensors (Basel, Switzerland) · 2020Article
- Green and Red Fluorescent Dyes for Translational Applications in Imaging and Sensing Analytes: A Dual-Color Flag.ChemistryOpen · 2018Review
- Near-Infrared Fluorescent Probes with Large Stokes Shifts for Sensing Zn(II) Ions in Living Cells.ACS sensors · 2016Article
- Quantitative imaging of glutathione in live cells using a reversible reaction-based ratiometric fluorescent probe.ACS chemical biology · 2015Article
- Carbamodithioate-based dual functional fluorescent probe for Hg(2+) and S(2-).Journal of fluorescence · 2014Article
- Addition of a second binding site increases the dynamic range but alters the cellular localization of a red fluorescent probe for mobile zinc.Inorganic chemistry · 2014Article
- Combinatorial actions of Tgfβ and Activin ligands promote oligodendrocyte development and CNS myelination.Development (Cambridge, England) · 2014Article
- Two-photon imaging of Zn2+ dynamics in mossy fiber boutons of adult hippocampal slices.Proceedings of the National Academy of Sciences of the United States of America · 2014Article
Corrections and comments
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6 authors.
Funding
Abstract
QZ1, 2-[2-chloro-6-hydroxy-3-oxo-5-(quinolin-8-ylaminomethyl)-3H-xanthen-9-yl]benzoic acid, and QZ2, 2-[6-hydroxy-3-oxo-4,5-bis-(quinolin-8-ylaminomethyl)-3H-xanthen-9-yl]benzoic acid, two fluorescein-based dyes derivatized with 8-aminoquinoline, have been prepared and their photophysical, thermodynamic, and zinc-binding kinetic properties determined. Because of their low background fluorescence and highly emissive Zn(II) complexes, QZ1 and QZ2 have a large dynamic range, with approximately 42- and approximately 150-fold fluorescence enhancements upon Zn(II) coordination, respectively. These dyes have micromolar K(d) values for Zn(II) and are selective for Zn(II) over biologically relevant concentrations of the alkali and alkaline earth metals. The Zn(II) complexes also fluoresce brightly in the presence of excess Mn(II), Fe(II), Co(II), Cd(II), and Hg(II), offering improved specificity for Zn(II) over di(2-picolyl)amine-based Zn(II) sensors. Stopped-flow kinetic investigations indicate that QZ1 and QZ2 bind Zn(II) with k(on) values of (3-4) x 10(6) M(-1) s(-1), compared to (6-8) x 10(5) M(-1) s(-1) for select ZP (Zinpyr) dyes, at 4.3 degrees C. Dissociation of Zn(II) from QZ1 and QZ2 occurs with k(off) values of 150 and 160 s(-1), over 5 orders of magnitude larger than those for ZP probes, achieving reversibility on the biological (millisecond) time scale. Laser scanning confocal and two-photon microscopy studies reveal that QZ2 is cell-permeable and Zn(II)-responsive in vivo. Because of its weaker affinity for Zn(II), QZ2 responds to higher concentrations of intracellular Zn(II) than members of the ZP family, illustrating that binding affinity is an important parameter for Zn(II) detection in vivo.
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