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Evaluation of 1,4-naphthoquinone derivatives as antibacterial agents:activity and mechanistic studies

Frontiers of Environmental Science & Engineering 2023年第3期17卷 49-61页

作者： Zhizhuo Liu Zhemin Shen Shouyan Xiang Yang sun Jiahua Cui Jinping Jia School of Environmental Science&Engineering Shanghai Jiao Tong UniversityShanghai 200240China School of Chemistry and Chemical Engineering Shanghai Jiao Tong UniversityShanghai 200240China

The diverse and large-scale application of disinfectants posed potential health risks and caused ecological damage during the 2019-nCoV pandemic,thereby increasing the demands for the development of disinfectants based on natural products,with low health risks and low aquatic *** the present study,a few natural naphthoquinones and their derivatives bearing the 1,4-naphthoquinone skeleton were synthesized,and their antibacterial activity against selected bacterial strains was *** vitro antibacterial activities of the compounds were investigated against Escherichia coli and Staphylococcus *** the minimum inhibitory concentration(MIC)of≤0.125μmol/L for juglone(1a),5,8-dimethoxy-1,4-naphthoquinone(1f),and 7-methyl-5-acetoxy-1,4-naphthoquinone(3),a strong antibacterial activity against *** was *** 1,4-naphthoquinone derivatives exhibited a strong antibacterial activity,with MIC values ranging between 15.625 and 500μmol/Land ECso values rangingbetween10.56 and248.42μmol/*** of the synthesized compounds exhibited strong antibacterial activities against *** these compounds,juglone(la)showed the strongest antibacterial *** results from mechanistic investigations indicated that juglone,a natural naphthoquinone,caused cell death by inducing reactive oxygen species production in bacterial cells,leading to DNA *** addition,juglone could reduce the self-repair ability of bacterial DNA by inhibiting RecA *** addition to having a potent antibacterial activity,juglone exhibited low cytotoxicity in cell-based *** conclusion,juglone is a strong antibacterial agent with low toxicity,indicating that its application as a bactericidal agent may be associated with low health risks and aquatic toxicity.

关键词： 1,4-naphthoquinone derivatives Antibacterial actionmechanism RecA

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