A bright, red-emitting water-soluble BODIPY fluorophore as an alternative to the commercial Mito Tracker Red for high-resolution mitochondrial imaging

Abstract

With the emergency and rapid development of super-resolution fluorescence microscopy, monitoring mitochondrial morphological changes has arouse researcher’s great interest to explore the role of mitochondria in the process of cell...

Mitochondria-targeted BODIPY dyes for small molecule recognition, bio-imaging and photodynamic therapy

“…To enable super-resolution observation of mitochondria, in 2021, Jiang et al reported a mitochondria-specific fluorogenic probe 11 , using TPP + and two quaternary ammonium cations as the targeting moiety. 90 Cell experiments proved that 11 possesses excellent photobleaching resistance and low phototoxicity, and is expected to be an alternative to the commercial Mito Tracker Red (Fig. 2B).…”

Recent Advances in N-Heterocyclic Small Molecules for Synthesis and Application in Direct Fluorescence Cell Imaging

“…A year later, Jiang and co-workers reported two novel fluorescent BODIPY dyes, 3 and 4 , for mitochondrial imaging ( Scheme 3 a) [ 21 ]. Lipophilic BODIPY 3 was afforded through a Knoevenagel condensation of 4-dimethylaminobenzaldehyde with the corresponding BODIPY.…”

“…( a , d ) MTG under a green channel (488 nm), ( b , e ) BODIPYs 4 and 3 under a red channel, and ( c , f ) merged images. Adapted from [ 21 ].…”

Parallel G-Quadruplex DNA Structures from Nuclear and Mitochondrial Genomes Trigger Emission Enhancement in a Nonfluorescent Nano-aggregated Fluorine–Boron-Based Dye

“…The coumarin core can be combined with, for example, quinazolines, benzothiazoles, benzoimidazoles, and amidines to give compounds that combine fluorescent properties with G4 binding and stabilizing properties. , Along the same line, dipyrro-boradiazaindacenes (BODIPY) dyes have great potential in the field of fluorescent sensing and bioimaging because of their excellent photophysical properties, relatively high photostability, and neutral total charge. , Unfortunately, with some exceptions, − the strong intermolecular interactions exerted by the planar π-conjugated BODIPY-units, in aqueous solution, strongly quench the fluorescence intensity through activation of fast nonradiative decay pathways, narrowing their practical applications . Here, by building on this knowledge, we designed a benzimidazole–iminocoumarin fused with a fluorine–boron unit that resembles the BODIPY core to generate a self-assembled dye, hereafter 4b , capable of recovering its intense fluorescence in response to binding to parallel G4s through the recognition-induced disassembly of the nonemissive aggregates (Figure ).…”