Recent Developments in the Design of New Water-Soluble Boron Dipyrromethenes and Their Applications: An Updated Review

Abstract

Boron-dipyrromethene (BODIPY) and its derivatives play an important role in the area of organic fluorophore chemistry. Recently, the water-soluble boron-dipyrromethene dyes have increasingly received interest. The structural modification of the BODIPY core by incorporating different neutral and ionic hydrophilic groups makes it water-soluble. The important hydrophilic groups, such as quaternary ammonium, sulfonate, oligoethylene glycol, dicarboxylic acid, and sugar moieties significantly increase the solubility of these dyes in water while preserving their photophysical properties. As a result, these fluorescent dyes are utilized in aqueous systems for applications such as chemosensors, cell imaging, anticancer, biolabeling, biomedicine, metal ion detection, and photodynamic treatment. This review covers the most current developments in the design and synthesis of water-soluble BODIPY derivatives and their wide applications since 2014.

Zwitterionic Polysulfobetaine Inhibits Cancer Cell Migration Owing to Actin Cytoskeleton Dynamics

“…The cellular internalization and specific localization of PZI-F were investigated by using confocal microscopy. Bright fluorescence intensity of BODIPY-based compounds made them useful as a distinct marker inside various cellular subdomains. , Several BODIPY-based water-soluble polymers and polymeric nanoparticles were explored in the literature for specific cellular imaging. , Thus, the strong green emissive BODIPY moiety along with zwitterion units in PZI-F makes this polymer suitable for cellular studies. Before cell imaging, the biocompatibility of PZI-F was assessed by testing its cellular cytotoxicity on HeLa cells using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay.…”

Bis(pinacoloto)diboron/4-Phenylpyridine System for One-Pot Photocatalyzed Borylation and Reduction of Aldehyde: Synthesis of Tavaborole in a Flow Reactor

“…Boron compounds such as BODIPY have been found as molecular probes and sensors. 2b In recent years, researchers have discovered compounds containing more than one boron atom such as carboranes, boron cage compounds, etc. 2a This has opened a new avenue for design of new boron containing drug molecules.…”

Synthesis of Bodipy-Tagged Galactoconjugates and Evaluation of Their Antibacterial Properties

“…Boron Dipyrromethene difluoride (BODIPY) derivatives are usually chosen as dyes for many applications in the biological and medicinal fields [9], such as molecular imaging and luminescence-guided surgery, due to their high absorption coefficients in the visible region, good luminescence properties, high photostability, weak dependence on environmental conditions, small size, and finally their chemical versatility for core modification with target molecules [10]. For practical applications, the use of at least two different BODIPY derivatives on a molecular platform [11], with close proximity and significant spectral overlap, is encouraged by the high fluorescence quantum yields and large Stokes shifts of such bichromophoric species, with a high difference between the excitation and the emission energy, which allow the suppression of photon scattering and diminish tissue autofluorescence in fluorescence imaging [12].…”