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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

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

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Abstract

© 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

URL: https://doi.org/10.1080/07391102.2019.1701555

DOI: 10.1080/07391102.2019.1701555

PubMed id: 31809642

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