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

BDE

bond dissociation energy

BODIPY

boron–dipyrromethane

Ddl

D-alanine:D-alanine ligase

DDQ

2,3-dichloro-5,6-dicyano-1,4-benzoquinone

DFT

density functional theory

DNA

deoxyribonucleic acid

DPPH

1,1‒diphenyl‒2‒picrylhydrazyl

NBS

N-bromo succinimide

ROS

reactive oxygen species

UV–vis

ultraviolet–visible

FMO

frontier molecular orbitals

HOMO

highest occupied molecular orbital

LUMO

lowest 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