Dataset Information

Fluorescence Sensing of Zinc and Mercury Ions with Hydrophilic 1,2,3-Triazolyl Fluorene Probes.

ABSTRACT: The ability to rapidly detect biologically and environmentally significant metal ions such as zinc and mercury is important to study a number of important cellular and environmental processes. Hydrophilic bis(1,2,3-triazolyl)fluorene-based derivatives, containing a 1,2,3-triazole-based recognition moiety, were synthesized through Click chemistry and characterized by UV-vis absorption, fluorescence emission, and two-photon absorption as new fluorescence sensing probes, selective for Zn(2+) and Hg(2+) ions. The UV-vis absorption and fluorescence emission spectra of the complexes exhibited blue-shifted absorption and emission spectra upon chelation to Zn(2+) and Hg(2+) ions, resulting in ca. two-fold enhancement in fluorescence. Fluorometric titration revealed that 1:2 and 1:3 ligand to metal complexes formed with binding constants of 10(8) and 10(16) for Zn(2+) and Hg(2+), respectively. The two-photon absorption cross sections for the probes and probe-metal ion complexes ranged from 200-350 GM at 800 nm. These novel fluorescent compounds may have potential as new metal ion sensors to probe cellular and biological environments.

SUBMITTER: Nguyen DM

PROVIDER: S-EPMC2888523 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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Fluorescence Sensing of Zinc and Mercury Ions with Hydrophilic 1,2,3-Triazolyl Fluorene Probes.

Nguyen Dao M DM Frazer Andrew A Rodriguez Luis L Belfield Kevin D KD

Chemistry of materials : a publication of the American Chemical Society 20100601 11

The ability to rapidly detect biologically and environmentally significant metal ions such as zinc and mercury is important to study a number of important cellular and environmental processes. Hydrophilic bis(1,2,3-triazolyl)fluorene-based derivatives, containing a 1,2,3-triazole-based recognition moiety, were synthesized through Click chemistry and characterized by UV-vis absorption, fluorescence emission, and two-photon absorption as new fluorescence sensing probes, selective for Zn(2+) and Hg ...[more]

PMID: 20577581

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Project description:In addition to being a covalent linker in molecular conjugation chemistry, the function of a 1,2,3-triazolyl moiety resulting from the copper(I)-catalyzed azide-alkyne cycloaddition reaction as a ligand for metal ions is receiving considerable attention. In this work, we characterize the thermodynamic and kinetic effects of incorporating a 1,2,3-triazolyl group in a multidentate ligand scaffold on metal coordination in the context of fluorescent zinc(II) indicator development. Ligands L14, BrL14, and FL14 (1,4-isomers) contain the 1,4-disubstituted-1,2,3-triazolyl group that is capable of binding with zinc(II) in conjunction with a di(2-picolylamino) (DPA) moiety within a multidentate ligand scaffold. Therefore, the 1,2,3-triazolyl in the 1,4-isomers is "integrated" in chelation. The 1,5-isomers L15, BrL15, and FL15 contain 1,2,3-triazolyls that are excluded from participating in zinc(II) coordination. These 1,2,3-triazolyls are "passive linkers". Zinc(II) complexes of 2:1 (ligand/metal) stoichiometry are identified in solution using (1)H NMR spectroscopy and isothermal titration calorimetry (ITC) and, in one case, characterized in the solid state. The 1:1 ligand/zinc(II) affinity ratio of L14 over L15, which is attributed to the affinity enhancement of a 1,2,3-triazolyl group to zinc(II) over that of the solvent acetonitrile, is quantified at 18 (-1.7 kcal/mol at 298 K) using an ITC experiment. Fluorescent ligands FL14 and FL15 are evaluated for their potential in zinc(II) sensing applications under pH neutral aqueous conditions. The 1,4-isomer FL14 binds zinc(II) both stronger and faster than the 1,5-isomer FL15. Visualization of free zinc(II) ion distribution in live HeLa cells is achieved using both FL14 and FL15. The superiority of FL14 in staining endogenous zinc(II) ions in live rat hippocampal slices is evident. In summation, this work is a fundamental study of 1,2,3-triazole coordination chemistry, with a demonstration of its utility in developing fluorescent indicators.

Dataset Information

Fluorescence Sensing of Zinc and Mercury Ions with Hydrophilic 1,2,3-Triazolyl Fluorene Probes.

Publications

Fluorescence Sensing of Zinc and Mercury Ions with Hydrophilic 1,2,3-Triazolyl Fluorene Probes.

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