Illuminating the Path to Enhanced Bioimaging by Phosphole‐based Fluorophores

Abstract

As the research of biological systems becomes increasingly complex, there is a growing demand for fluorophores with a diverse range of wavelengths. In this study, we introduce phosphole‐based fluorophores that surpass existing options like dansyl chloride. The reactive S‐Cl bond in chlorosulfonylimino‐5‐phenylphosphole derivatives allows rapid and direct coupling to peptides making the fluorophores easily introducible to peptides. This coupling process occurs under mild conditions, demonstrated for [F7, P34]‐NPY and its shorter analogues. Peptides linked with our fluorophores exhibit similar receptor activation to the control peptide, while maintaining high stability and low toxicity, making them ideal biolabeling reagents. In fluorescence microscopy experiments, they can be easily visualized even at low concentrations, without suffering from the typical issue of bleaching. These phosphole‐based fluorophores represent a significant leap forward in the field. Their versatility, ease of modification, superior performance, and applicability in biological labeling make them a promising choice for researchers seeking advanced tools to unravel the details of complex biological systems.

Thieno[3,2-b]phosphole-based AIEgens: facile preparation and dual modulation of solid-state luminescence

“…Phospholes are a class of phospha-cyclopentadienes 32 that exhibit unique electronic and structural properties, making them highly suitable for modulating the emission characteristics of fluorophores. 33–45 Phosphole-based fluorophores have demonstrated efficacy in diverse applications, including organic light-emitting diodes (OLEDs) 46–48 and biomolecular imaging, 49–51 thus underscoring their utility and versatility. Benzo- and thieno-annellated phosphole oxides emerge as highly advantageous candidates for achieving color tunability in fluorophores due to their favorable electron-acceptor properties (Fig.…”

Enantioselective Synthesis of P-Chirogenic 1,2,3-Triazolobenzophospholes

“…Dibenzophospholes and fused heteroaromatic derivatives have attracted increasing interest for their applications in organic optoelectronic materials, catalysis and bioimaging . Chiral versions of dibenzophospholes or derivatives have been developed and proved to be suitable ligands , or Lewis-bases in asymmetric catalysis or organocatalysis, respectively.…”