Abstract
We present a series of newly designed 2,1,3-benzothiadiazole (BTD)-containing imidazole(ium) derivatives that are selective live cell fluorescence imaging probes applied in bioimaging experiments. The attachment of imidazole(ium) moieties that are planar, rigid, flat and displays strong hydrogen bond sites allows modulating the physicochemical properties of the resulting fluorescent bioimaging molecular probes which are water-soluble at room temperature. The photophysical characterization revealed the high stability of those derivatives in both the ground and excited states meaning the relaxation processes take place with no degradation. DFT calculations showed the orbital behavior of the fluorescent compounds pointing to the origin of the high chemical stability of such compounds in their relaxation processes from the excited states (no degradation noted). Live cell fluorescence imaging experiments (MCF-7 breast cancer cell lineage and other types) showed a high subcellular selection inside the cells and lysosomes could be selectively stained. Bioimaging experiments also revealed that all compounds were capable of transpose the cellular membrane and one of them showed impressive selection towards lysosomes with intense, bright and green fluorescence. The BTD derivatives proved to be cell penetrating and stable in solution storage at room temperature, which represents a huge advance over the commercially available cellular markers.
Published Version
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