ArticleInorganic chemistry2013
Integrated and passive 1,2,3-triazolyl groups in fluorescent indicators for zinc(II) ions: thermodynamic and kinetic evaluations.
Article in Inorganic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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9 citing papers in PubMed, 74 citations in OpenAlex.
- Article
- Synthesis and biological evaluation of zinc chelating compounds as metallo-β-lactamase inhibitors.MedChemComm · 2019Article
- Structural Determinants of Alkyne Reactivity in Copper-Catalyzed Azide-Alkyne Cycloadditions.Molecules (Basel, Switzerland) · 2016Article
- Convergent Synthesis of Two Fluorescent Ebselen-Coumarin Heterodimers.Pharmaceuticals (Basel, Switzerland) · 2016Article
- Enhancing the Photostability of Arylvinylenebipyridyl Compounds as Fluorescent Indicators for Intracellular Zinc(II) Ions.The Journal of organic chemistry · 2015Article
- Bi-8-carboxamidoquinoline derivatives for the fluorescent recognition of Zn2+.Journal of fluorescence · 2015Article
- A fluorescent indicator for imaging lysosomal zinc(II) with Förster resonance energy transfer (FRET)-enhanced photostability and a narrow band of emission.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- Biologically targeted probes for ZnChemical science · 2014Article
- Zn(II)-coordination modulated ligand photophysical processes - the development of fluorescent indicators for imaging biological Zn(II) ions.RSC advances · 2014Article
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7 authors at 2 institutions in 1 country.
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Abstract
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.
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