Two new coumarin-based “turn-off” fluorescent probes, ( E)-3-((3,4-dihydroxybenzylidene)amino)-7-hydroxy-2 H-chromen-2-one ( BS1) and ( E)-3-((2,4-dihydroxybenzylidene)amino)-7-hydroxy-2 H-chromen-2-one ( BS2), were synthesized and their detection of copper(II) and iron(III) ions was studied. Results show that both compounds are highly selective for Cu 2+ and Fe 3+ ions over other metal ions. However, BS2 is detected directly, while detection of BS1 involves a hydrolysis reaction to regenerate 3-amino-7-hydroxycoumarin ( 3) and 3,4-dihydroxybenzaldehyde, of which 3 is able to react with copper(II) or iron(III) ions. The interaction between the tested compounds and copper or iron ions is associated with a large fluorescence decrease, showing detection limits of ca. 10 ？5 M. Preliminary studies employing epifluorescence microscopy demonstrate that Cu 2+ and Fe 3+ ions can be imaged in human neuroblastoma SH-SY5Y cells treated with the tested probes.
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