https://orcid.org/0000-0003-0749-590X
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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
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.
