A new chiral boron-dipyrromethene (BODIPY)-based fluorescent probe: molecular docking, DFT, antibacterial and antioxidant approaches

A new chiral BODIPY-based fluorescent compound, 5-bromo-4,4-difluoro-3(S)-1-phenylethyl)amino) BODIPY, <b>4</b> was synthesized for biomedical applications. Optical, antimicrobial, antioxidant properties of the compound <b>4</b> are investigated. The partition coefficient suggested that the compound <b>4</b> has the potential to be developed as an active antibacterial and antioxidant candidate. In this context, antibacterial assay was carried out for compound <b>4</b> against various bacterial strains, revealing maximum inhibition zone (24 ± 2.19 mm) in <i>Escherichia coli.</i> Moreover, results of antioxidant activity of compound <b>4</b> revealed IC₅₀ values to be greater than ascorbic acid. Molecular docking has given brief insight about the binding of the compound <b>4</b>, suggesting that it has a strong potential to inhibit bacterial target enzymes <i>viz.,</i> DNA gyrase, enzymes in the type II fatty acid synthesis and Ddl (d-alanine: d-alanine ligase) in peptidoglycan synthesis. The molecular geometry and electrostatic potential of compound <b>4</b>, was established by DFT (Density Functional Theory) calculations. AbbreviationsBBBblood‒brain barrierBDEbond dissociation energyBODIPYboron–dipyrromethaneDdlD-alanine:D-alanine ligaseDDQ2,3-dichloro-5,6-dicyano-1,4-benzoquinoneDFTdensity functional theoryDNAdeoxyribonucleic acidDPPH1,1‒diphenyl‒2‒picrylhydrazylNBS<i>N</i>-bromo succinimideROSreactive oxygen speciesUV–visultraviolet–visibleFMOfrontier molecular orbitalsHOMOhighest occupied molecular orbitalLUMOlowest unoccupied molecular orbital blood‒brain barrier bond dissociation energy boron–dipyrromethane D-alanine:D-alanine ligase 2,3-dichloro-5,6-dicyano-1,4-benzoquinone density functional theory deoxyribonucleic acid 1,1‒diphenyl‒2‒picrylhydrazyl <i>N</i>-bromo succinimide reactive oxygen species ultraviolet–visible frontier molecular orbitals highest occupied molecular orbital lowest unoccupied molecular orbital Communicated by Ramaswamy H. Sarma