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1,4-Naphthoquinone Analogues: Potent Antibacterial Agents and Mode of Action Evaluation

Department of Life Science, Department of Energy Storage/Conversion Engineering of Graduate School, and Hydrogen and Fuel Cell Research Center, Chonbuk National University, Jeollabuk-do 54896, Korea
Department of Forest Science and Technology, College of Agriculture and Life Sciences, Chonbuk National University, 567 Baekje-daero, Deokjin-gu, Jeonju-si 561-756, Jeollabuk-do, Korea
Department of Biotechnology, Karunya Institute of Technology and Science, School of Agriculture and Biosciences, Karunya Nagar, Coimbatore 641114, Tamil Nadu, India
R&D Center for CANUTECH, Business Incubation Center, Department of Bioenvironmental Chemistry, Chonbuk National University, Jeollabuk-do 54896, Korea
Authors to whom correspondence should be addressed.
Molecules 2019, 24(7), 1437;
Received: 15 March 2019 / Revised: 2 April 2019 / Accepted: 4 April 2019 / Published: 11 April 2019
(This article belongs to the Section Medicinal Chemistry)
PDF [4361 KB, uploaded 11 April 2019]


1,4-Naphthoquinones have antibacterial activity and are a promising new class of compound that can be used to treat bacterial infections. The goal was to improve effective antibacterial agents; therefore, we synthesized a new class of naphthoquinone hybrids, which contain phenylamino-phenylthio moieties as significant counterparts. Compound 4 was modified as a substituted aryl amide moiety, which enhanced the antibacterial activity of earlier compounds 3 and 4. In this study, five bacterial strains Staphylococcus aureus (S. aureus), Listeria monocytogenes (L. monocytogenes), Escherichia coli (E. coli), Pseudomonas aeruginosa (P. aeruginosa) and Klebsiella pneumoniae (K. pneumoniae) were used to evaluate the antibacterial potency of synthesized naphthoquinones using the minimal inhibitory concentration (MIC) method. Most of the studied naphthoquinones demonstrated major antibacterial activity with a MIC of 15.6 µg/mL–500 µg/mL. Selected compounds (5a, 5f and 5x) were studied for the mode of action, using intracellular ROS generation, determination of apoptosis by the Annexin V-FITC/PI assay, a bactericidal kinetic study and in silico molecular modelling. Additionally, the redox potentials of the specified compounds were confirmed by cyclic voltammetry (CV). View Full-Text
Keywords: quinones; ROS generation; apoptosis; kinetic study quinones; ROS generation; apoptosis; kinetic study

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Ravichandiran, P.; Sheet, S.; Premnath, D.; Kim, A.R.; Yoo, D.J. 1,4-Naphthoquinone Analogues: Potent Antibacterial Agents and Mode of Action Evaluation. Molecules 2019, 24, 1437.

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