Curcumin-Derived Turn-Off Fluorescent Probe for Copper (II) Ion Detection and Live Cell Imaging Applications

A curcumin-derived chemosensor 4,4′-((1E,3Z,5Z,6E)-3,5-bis((2hydroxyphenyl)imino) hepta-1,6-diene-1,7-diyl)bis(2-methoxyphenol) (HIBMP) was developed from curcumin and o-aminophenol using Schiff base condensation method. HIBMP selectively recognizes Cu (II) ion (Cu (II)) relative to other tested metal ions. Selective binding of Cu (II) ion turns off the fluorescent property of HIBMP and shows no interference with other metal ions. Moreover, the favourable binding of Cu (II) with HIBMP was noticed by a good linearity between the fluorescence intensity and concentration of Cu (II) with a range of 0–15.6 × 10⁻⁷ M, and the limit of detection was determined to be as low as 30.1 nM. Furthermore a 1:1 stoichiometry was identified from the results of Job's plot and HR-MS. Density functional theory (DFT) calculation results expressed that the intramolecular charge transfer (ICT) during chelation is responsible for quenching of fluorescence. Besides, the fluorescence life time measurement and ethylenediaminetetraacetic acid (EDTA) titration method revealed the stability and reversibility of the sensor. Practical use of the sensor was achieved through the quantitative analysis of spiked Cu (II) ion in real water samples with good recoveries, and biological experiments exposed that the sensor was less toxic and could be applied in fluorescence imaging of Cu (II) in living cells.