Circularly Polarized Luminescence Bioimaging Using Chiral BODIPYs: A Model Scaffold for Advancing Unprecedented CPL Microscopy Using Small Full-Organic Probes.

Unprecedented circularly polarized luminescence bioimaging (CPL-bioimaging) of live cells using small full-organic probes is first reported. These highly biocompatible and adaptable probes are pivotal to advance emerging CPL Laser-Scanning Confocal Microscopy (CPL-LSCM) as an undeniable tool to distinguish, monitor, and understand the role of chirality in the biological processes. The development of these probes was challenging due to the poor dichroic character associated with the involved CPL emissions.

Polar ammoniostyryls easily converting a clickable lipophilic BODIPY in an advanced plasma membrane probe.

A very simple, small and symmetric, but highly bright, photostable and functionalizable molecular probe for plasma membrane (PM) has been developed from an accessible, lipophilic and clickable organic dye based on BODIPY. To this aim, two lateral polar ammoniostyryl groups were easily linked to increase the amphiphilicity of the probe and thus its lipid membrane partitioning. Compared to the BODIPY precursor, the transversal diffusion across lipid bilayers of the ammoniostyryled BODIPY probe was highly reduced, as evidenced by fluorescence confocal microscopy on model membranes built up as giant unilamellar vesicles (GUVs).