Abstract
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 IC
50
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.
Abbreviations
BBB
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
Communicated by Ramaswamy H. Sarma