Selective bioimaging of cancer cells and detection of HSA with indomethacin-based fluorescent probes.

Two fluorescent probes were designed by connecting indomethacin to coumarin through different linkers. The introduction of indomethacin quenched the fluorescence of coumarin-based probes with apparent red-shifts in the absorption and emission maxima, probably due to the photoinduced electron transfer (PET) from the indomethacin to the fluorophore and the formation of folding conformation. The addition of human serum albumin (HSA) triggered about 40-fold fluorescence enhancements of ADC-IMC-2 and ADC-IMC-6 with 85 nm blue-shifts. The probe with longer spacer ADC-IMC-6 exhibited ratiometric fluorescent response toward HSA, and that with shorter linker showed "off-on" fluorescence response to HSA. However, insignificant spectral changes of the reference compounds (ADC-6 and ADC-2) initiated by HSA implied that indomethacin played critical role in the identification of HSA. The competitive assays and molecular docking results reveal that the indomethacin in ADC-IMC-6 could tightly combine at drug site I of HSA. Fluorescence bio-imaging experiments show that both probes could distinguish cancer cells from normal cells.