The synthesis, photochemical properties, biological effects and the X-ray crystal structure of a fluorescent polyamine macrocycleLare reported.Lis 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.Lperforms 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.Lis 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 ofLat this pH value.Laffects 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,Lalmost completely abrogates the survival of the leukemic cells over 72 h, with a mechanism that is compatible with a genomic DNA interaction.

Zn(ii) detection and biological activity of a macrocycle containing a bis(oxadiazole)pyridine derivative as fluorophore / Ambrosi G.; Fanelli M.; Paoli P.; Formica M.; Paderni D.; Rossi P.; Micheloni M.; Giorgi L.; Fusi V.. - In: DALTON TRANSACTIONS. - ISSN 1477-9226. - STAMPA. - 49:(2020), pp. 7496-7506. [10.1039/c9dt03910d]

Zn(ii) detection and biological activity of a macrocycle containing a bis(oxadiazole)pyridine derivative as fluorophore

Paoli P.;Rossi P.;
2020

Abstract

The synthesis, photochemical properties, biological effects and the X-ray crystal structure of a fluorescent polyamine macrocycleLare reported.Lis 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.Lperforms 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.Lis 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 ofLat this pH value.Laffects 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,Lalmost completely abrogates the survival of the leukemic cells over 72 h, with a mechanism that is compatible with a genomic DNA interaction.
2020
49
7496
7506
Goal 3: Good health and well-being for people
Ambrosi G.; Fanelli M.; Paoli P.; Formica M.; Paderni D.; Rossi P.; Micheloni M.; Giorgi L.; Fusi V.
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/1208749
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