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

Lookup NU author(s): Rua Alnoman, Dr Julian Knight



This is the authors' accepted manuscript of an article that has been published in its final definitive form by Taylor and Francis Ltd, 2020.

For re-use rights please refer to the publisher's terms and conditions.


© 2019, © 2019 Informa UK Limited, trading as Taylor & Francis Group. 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 barrierBDE bond dissociation energyBODIPY boron–dipyrromethaneDdl D-alanine:D-alanine ligaseDDQ 2,3-dichloro-5,6-dicyano-1,4-benzoquinoneDFT density functional theoryDNA deoxyribonucleic acidDPPH 1,1‒diphenyl‒2‒picrylhydrazylNBSN-bromo succinimideROS reactive oxygen speciesUV–vis ultraviolet–visibleFMO frontier molecular orbitalsHOMO highest occupied molecular orbitalLUMO lowest unoccupied molecular orbital Communicated by Ramaswamy H. Sarma.

Publication metadata

Author(s): Alnoman RB, Parveen S, Hagar M, Ahmed HA, Knight JG

Publication type: Article

Publication status: Published

Journal: Journal of Biomolecular Structure and Dynamics

Year: 2020

Volume: 38

Issue: 18

Pages: 5429-5442

Online publication date: 06/12/2019

Acceptance date: 02/12/2019

Date deposited: 11/02/2020

ISSN (print): 0739-1102

ISSN (electronic): 1538-0254

Publisher: Taylor and Francis Ltd


DOI: 10.1080/07391102.2019.1701555

PubMed id: 31809642


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