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Multi‐Use NBD‐Based Tetra‐amino Macrocycle: Fluorescent Probe for Metals and Anions and Live Cell Marker
Author(s) -
Amatori Stefano,
Ambrosi Gianluca,
Fanelli Mirco,
Formica Mauro,
Fusi Vieri,
Giorgi Luca,
Macedi Eleonora,
Micheloni Mauro,
Paoli Paola,
Pontellini Roberto,
Rossi Patrizia,
Varrese Maria Antonietta
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103135
Subject(s) - fluorescence , chemistry , acetonitrile , halide , ligand (biochemistry) , metal , metal ions in aqueous solution , chelation , photochemistry , crystallography , inorganic chemistry , receptor , organic chemistry , biochemistry , physics , quantum mechanics
Ligand L (4‐(7‐nitrobenzo[1,2,5]oxadiazole‐4‐yl)‐1,7‐dimethyl‐1,4,7,10‐tetra‐azacyclododecane) is a versatile fluorescent sensor useful for Cu II , Zn II and Cd II metal detection, as a building block of fluorescent metallo‐receptor for halide detection, and as an organelle marker inside live cells. Ligand L undergoes a chelation‐enhanced fluorescence (CHEF) effect upon metal coordination in acetonitrile solution. In all three complexes investigated the metal cation is coordinatively unsaturated; thus, it can bind secondary ligands as anionic species. The crystal structure of [Zn L Cl](ClO 4 ) is discussed. Cu II and Zn II complexes are quenched upon halide interaction, whereas the [Cd L ] 2+ species behaves as an OFF–ON sensor for halide anions in acetonitrile solution. The mechanism of the fluorescence response in the presence of the anion depends on the nature of the metal ion employed and has been studied by spectroscopic methods, such as NMR spectroscopy, UV/Vis and fluorescence techniques and by computational methods. Subcellular localization experiments performed on HeLa cells show that L mainly localizes in spot‐like structures in a polarized portion of the cytosol that is occupied by the Golgi apparatus to give a green fluorescence signal.