Zn2+/Cd2+ optical discrimination by fluorescent chemosensors based on 8-hydroxyquinoline derivatives and sulfur-containing macrocyclic units

M. Carla Aragoni, Massimiliano Arca, Andrea Bencini, Claudia Caltagirone, Alessandra Garau, Francesco Isaia, Mark E. Light, Vito Lippolis, Carlos Lodeiro, Marta Mameli, Riccardo Montis, M. Cristina Mostallino, Anna Pintus, Stefano Puccioni

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Four new fluorescent chemosensors for metal ions based on 8-hydroxyquinoline (8-HDQ) derivatives and sulfur-containing macrocyclic units were synthesized and characterized, namely 1-(5-chloro-8-hydroxy-7- quinolinylmethyl)-1-aza-4,7,10-trithiacyclododecane (L1), 1-(5-chloro-8-hydroxy- 7-quinolinylmethyl)-1-aza-4,13-dithia-7,10-dioxacyclopentadecane (L2), 1-(8-hydroxy-2-quinolinylmethyl)-1-aza-4,7,10-trithiacyclododecane (L3), and 1-(8-hydroxy-2-quinolinylmethyl)-1-aza-4,13-dithia-7,10-dioxacyclopentadecane (L4). Preliminary fluorimetric titrations indicated L1 as the only member of the family of ligands to give a selective CHEF-type response to the presence of Zn2+ in MeCN-H2O (1:1, v/v) solutions, which allowed imaging of this metal ion in Cos-7 cells in vitro. The other ligands either did not show any fluorescence response (L3, L4) to any of the metal ions considered (Cu2+, Zn2+, Cd2+, Hg2+ and Pb 2+) or gave (L2) a CHEF-type response also to the presence of Cd 2+. The coordination properties of L1 towards Zn2+ were, therefore, fully investigated by potentiometric measurements and absorption and emission spectroscopy at different pH values, which indicated that the formation of 2:1 L1/Zn2+ complexes is responsible for the CHEF-type effect observed. The complexes [Zn(L1)2H2O](BF4) 2 and [Zn(L3)](ClO4)2 were characterized in the solid state by X-ray crystallography, and DFT calculations were performed to understand the origin of the Zn2+/Cd2+ optical discrimination of the 8-HDQ-based "conjugate" fluorescent chemosensors reported.

    Original languageEnglish
    Pages (from-to)14516-14530
    Number of pages15
    JournalDalton Transactions
    Volume42
    DOIs
    Publication statusPublished - 2013

    Keywords

    • 8-Hydroxyquinoline
    • 8-hydroxyquinoline derivatives
    • Absorption and emission spectroscopy
    • Coordination properties
    • DFT calculation
    • Fluorescent chemosensors
    • Fluorimetric titration
    • Potentiometric measurements
    • Emission spectroscopy
    • Fluorescence
    • Lead
    • Ligands
    • Metal ions
    • Physiology
    • Sulfur
    • X ray crystallography
    • Zinc
    • Copper
    • 8 quinolinol
    • cadmium
    • fluorescent dye
    • macrocyclic compound
    • sulfur
    • zinc
    • Chlorocebus aethiops
    • COS 1 cell line
    • light related phenomena
    • spectrofluorometry
    • animal
    • chemical structure
    • chemistry
    • quantum theory
    • synthesis
    • article
    • COS Cells
    • Fluorescent Dyes
    • Macrocyclic Compounds
    • Models, Molecular
    • Molecular Structure
    • Optical Processes
    • Oxyquinoline

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