Simple Way to Fabricate Chiral Fluorescent Molecules and Chirality-Dependent Biomolecule Recognition and Cell Imaging

Abstract Employing chiral fluorescent molecules to enable a visual communication with bio-objects (enzymes, signaling molecules, and living cells, etc.) is meaningful but extremely challenging, and the fabrication of the chirality concept into the molecule’s architecture is a great obstacle for scientists. In this study, two chiral compounds (TPA-PyrT@CSAD and TPA-PyrT@CSAL) were obtained using an anion replacement strategy, which shares the same fluorescent skeleton of TPA-PyrT and the chiral anion of camphor sulfonic salt (CAS) with opposite configurations as D or L. First, the chirality-dependent recognition of several bio-molecules was realized; in addition, these probes were verified with obvious discriminating ability to cancer cells or normal cells, demonstrating different mitochondria-imaging capability and dynamic cell endocytosis processes. Owing to its excellent sensing performance, TPA-PyrT@CSAD was successfully applied to monitor the concentration fluctuations of O2•- in mitochondria. Finally, the in vivo biosafety was evaluated using zebrafish as a model.