Multi-use NBD-based tetra-amino macrocycle: fluorescent probe for metals and anions and live cell marker

Chemistry : a European Journal
Stefano AmatoriMaria Antonietta Varrese

Abstract

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 [ZnLCl](ClO(4)) is discussed. Cu(II) and Zn(II) complexes are quenched upon halide interaction, whereas the [CdL](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 gree...Continue Reading

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Citations

Feb 13, 2015·Chemical Society Reviews·Trent D AshtonFrederick M Pfeffer
Dec 18, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Elisa BorgogelliPatrizia Rossi
Jan 24, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Gianluca AmbrosiMario Inclán
Aug 30, 2019·Chemical Communications : Chem Comm·Jing YangZong-Wan Mao
Oct 25, 2013·Chemical Communications : Chem Comm·Xiaobo WangZhilin Wang
Feb 26, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Eleonora MacediVieri Fusi
Jan 25, 2020·Journal of Cell Science·Matthew ZajacYamuna Krishnan
May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mauro FormicaEnrique García-España
Apr 25, 2014·Inorganic Chemistry·Stefano AmatoriAurora Tassoni

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