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, 4 was synthesized for biomedical applications. Optical, antimicrobial, antioxidant properties of the compound 4 are investigated. The partition coefficient suggested that the compound 4 has the potential to be developed as an active antibacterial and antioxidant candidate. In this context, antibacterial assay was carried out for compound 4 against various bacterial strains, revealing maximum inhibition zone (24 ± 2.19 mm) in Escherichia coli. Moreover, results of antioxidant activity of compound 4 revealed IC50 values to be greater than ascorbic acid. Molecular docking has given brief insight about the binding of the compound 4, suggesting that it has a strong potential to inhibit bacterial target enzymes viz., 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 4, was established by DFT (Density Functional Theory) calculations. AbbreviationsBBB blood‒brain barrier BDEbond dissociation energy BODIPYboron–dipyrromethane DdlD-alanine:D-alanine ligase DDQ2,3-dichloro-5,6-dicyano-1,4-benzoquinone DFTdensity functional theory DNAdeoxyribonucleic acid DPPH1,1‒diphenyl‒2‒picrylhydrazyl NBSN-bromo succinimide ROSreactive oxygen species UV–visultraviolet–visible FMOfrontier molecular orbitals HOMOhighest occupied molecular orbital LUMOlowest 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 N-bromo succinimide reactive oxygen species ultraviolet–visible frontier molecular orbitals highest occupied molecular orbital lowest unoccupied molecular orbital Communicated by Ramaswamy H. Sarma