Zn(ii) detection and biological activity of a macrocycle containing a bis(oxadiazole)pyridine derivative as fluorophore. Issue 22 (22nd May 2020)

• Record Type: Journal Article
• Authors: Ambrosi, Gianluca; Fanelli, Mirco; Paoli, Paola; Formica, Mauro; Paderni, Daniele; Rossi, Patrizia; Micheloni, Mauro; Giorgi, Luca; Fusi, Vieri
• Is Part Of: Dalton transactions. Volume 49:Issue 22(2020)
• Page Start: 7496
• Page End: 7506
• Publication Date: 2020-05-22
• Subjects: Chemistry, Inorganic -- Periodicals; Chemistry, Physical and theoretical -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.05
• DOI: 10.1039/c9dt03910d
• Languages: English
• ISSNs: 1477-9226

Abstract

Abstract : A macrocyclic ligand able to detect Zn(ii ) and Cd(ii ) ions in aqueous solution at pH = 7 through a CHEF effect with antiproliferative properties is presented. Abstract : The synthesis, photochemical properties, biological effects and the X-ray crystal structure of a fluorescent polyamine macrocycle L are reported. L is a polyamine cyclophane macrocycle in which 2, 6-bis(5-(2-methylphenyl)-1, 3, 4-oxadiazol-2-yl)pyridine (POXAPy) acts as a fluorescent sensor and the polyamine as a metal ion binding unit. L performs as a PET-mediated chemosensor, with a maximum emission wavelength close to 360 nm. This gives rise to a signal that is visible to the naked eye in the blue visible range. L is able to detect the Zn(ii ) and Cd(ii ) metal ions in an aqueous solution at pH = 7, with the coordination of the ions switching the emission ON through a CHEF effect. In contrast, paramagnetic metal ions like Cu(ii ) and Ni(ii ) completely quench the already low emission of L at this pH value. L affects the cell survival of a leukemic cellular model (U937) at micromolar concentrations with cell death starting after only 24 h of exposure; starting from a final concentration of 5 μM, L almost completely abrogates the survival of the leukemic cells over 72 h, with a mechanism that is compatible with a genomic DNA interaction.