A new chiral boron-dipyrromethene (BODIPY)-based fluorescent probe: molecular docking, DFT, antibacterial and antioxidant approaches

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

Keywords:

• BODIPY
• antibacterial
• antioxidant
• molecular docking
• DFT

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.