A fluorescence "turn-on" probe for Cu (Ⅱ) based on flavonoid intermediates generated by copper-induced oxidative cyclization and its fluorescence imaging in living cells

Abstract

A fluorescence "turn-on" probe for Cu (Ⅱ) ions was prepared based on the condensation reaction of coumaraldehyde and 1-hydroxy-2-acetylnaphthalene. A strong fluorescent flavonoid intermediate was formed and verified by the NMR and ESI-MS experiments. The water-soluble and pH dependence experiments were performed to confirm the optimal solvent condition (CH₃CN: HEPES = 1:1, v/v, pH = 7.2-7.4). The dynamic experiments indicated that the formation process of the intermediate catalyzed by Cu(Ⅱ) ions was probably pseudo-first-order reaction process. The probe showed good selectivity toward copper ions and almost no interference except Ag⁺ ions by the selectivity and competitive experiments. The HeLa cells were used in the cell fluorescence imaging tests and it was demonstrated that the probe could be used in the phycological condition and showed weak cytotoxicity by the MTT experiments.

Keywords: Cell imaging; Copper ions detection; Oxidative cyclization; The flavonoid intermediate.