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 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.
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
Graphical Abstract
![](/cms/asset/5442568c-bb23-40dc-8edf-8549b4f9bd40/tbsd_a_1701555_uf0001_c.jpg)
Acknowledgements
Authors gratefully acknowledge the Deanship of Scientific Research, Taibah University for support of our research group (60229).
Disclosure statement
The authors have no conflicts to declare.