Regulation of the alkyl chain of fluorescent probes to selectively target the cell membrane or mitochondria in living cells

The visualization of cell membrane and mitochondrial behavior in living cells is of great life science value, but challenging due to the lack of ideal probes. In this work, two novel fluorescent probes based on different lengths of alkyl chains were reported for selective targeting of cell membranes or mitochondria of living cells. The probe CTM (1-Octadecyl-4-[9-ethyl-6-(diphenylamino)-9H-carbazol-3-yl] pyridinium) achieved cell membrane-specific staining in cells. Moreover, the probe CTM could monitor cell membrane damage through subcellular migration. Once the cell membrane was damaged, the probe CTM migrated into the mitochondria as a signal reporter. In addition, the probe MTM (1-Dodecly-4-[9-ethyl-6-(diphenylamino)-9H-carbazol-3-yl] pyridinium) with the shorter alkyl chain bearing the same skeleton structure penetrated the cell membrane and exhibited high affinity to mitochondria. This work will provide a useful tool to visualize the behavior of cell membranes and mitochondria in living cells.