Double labelling of intracellular mitochondria and nucleolus using thiophene pyridium salt with high quantum yield as biosensor and its application in stimulated emission depletion nanoscopy.

Probe for dual-site target distinct subcellular compartments from cytosol and nucleus is an attractive approach, however, which was scarcely reported. Herein, a series of small-molecular thiophene pyridium salt derivatives (MitoNuc1-4) possessing water-soluble, high quantum yield and two-photon activity were rationally designed, and their structures were crystallographic confirmed. Systematic photophysical and biological imaging property investigations were carried out for them. It was found that MitoNuc1-4 exhibit two-photon absorption properties in the near infrared region, and MitoNuc1 has membrane permeability and cationic nature, rendering it to be double labelling of mitochondria and nucleolus in living cells with superb photo-stability and non-invasiveness. It also demonstrated that MitoNuc1 in living cells can monitor mitochondrial division in real time and revealed nucleolar ultrastructure under stimulated emission depletion nanoscopy.