Thiazolidine based fluorescent chemosensors for aluminum ions and their applications in biological imaging

Utilization of fluorescent techniques in detection of various metal ions actively pursued allow ultrasensitive and selective detections of metal ions and prevent the adverse effect of cations such as aluminum (III) ions. In this study, two novel fluorescent chemosensors containing thiazole derivatives, ((E)-2-(4-hydroxy-3-(((2-hydroxyphenyl)imino)methyl)phenyl)-3-phenyl thiazolidin-4-one) AM1 and (2,3-bis(4-hydroxy-3-((E)-((2-hydroxyphenyl)imino) methyl) phenyl) thiazolidin-4-one) AM2, have been fabricated. The probes AM1 and AM2 were prepared using the condensation reaction between 2-hydroxy-5-(4-oxo-3-phenyl thiazolidin-2-yl) benzaldehyde and 2-aminophenol for the probe AM1 and 5,5′-(4-oxothiazolidine-2,3-diyl)bis(2-hydroxy benzaldehyde) and 2-aminophenol for the probe AM2. Afterwards, they were analyzed by various types of NMR and FT-IR spectroscopy, ESI-MS spectra, and elemental anayzer. As a second step, each fabricated chemosensor was able to use turn on fluorescence sensing for detecting of Al3+ ions in ACN/H2O (v/v = 50/50, 10.0 μM, pH = 7.0) solution. Clear complexes formed between the probe AM1 and Al3+ ions and also the probe AM2 and Al3+ ions was determined by not only 1H NMR titration study but also calculated by using the Job's plot. The limit of detection (LOD) value was found to be 0.11 μM (AM1) and 4.4 μM (AM2) for Al3+ ions. Likewise, cell imaging and in vitro cytotoxicity experiments of Al3+ ions in Human epithelium Lovo cells exhibited that prepared chemosensors had low cytotoxicity and blue fluorescence when they treated with of Al3+ ions in the cellular system.