Fungal Quinones: Benzo-, Naphtho-, and Anthraquinones

López, Víctor; Les, Francisco

doi:10.1007/978-3-031-18587-8_18

Cited by 1 publication

(1 citation statement)

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“…These compounds are known to possess a broad spectrum of biological activities, including antifungal, antibacterial, antiviral, and antiparasitic properties [8]. The antifungal activity of naphthoquinones is thought to be associated with their redox properties, which allow them to interact with essential cellular components, such as enzymes and fungal DNA [20]. The structure-activity relationship of naphthoquinones is complex and varies depending on the substituents on the naphthoquinone ring [21].…”

Section: Discussionmentioning

confidence: 99%

Antifungal Potential, Mechanism of Action, and Toxicity of 1,4-Naphthoquinone Derivatives

Almeida,

Fonseca,

Cortez

et al. 2023

Preprint

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The increase in fungal infections, accompanied by adverse effects and acquired resistance associated with the use of antifungal agents used for their clinical management, have facilitated the search for new substances with antifungal properties. Naphthoquinones have been investigated due to their multiple biological activities, including their significant antifungal potential. This study aimed at evaluating the antifungal potential of naphthoquinones against opportunistic fungi and dermatophytes and to assess the impact of a selected naphthoquinone on the formation of the cell wall, ergosterol membrane, and cellular membrane of Candida albicans ATCC 60193. Additionally, cytotoxicity in the MRC-(Medical Research Council-)5 cell lineage, Artemia salina, and tomato as well as arugula seeds was evaluated. The antifungal activity of four naphthoquinones was assessed using well-characterized fungal strains, the minimum inhibitory concentration (MIC) was determined applying the microdilution assay technique. Antifungal activity of the assessed naphthoquinones could be confirmed, particularly for 2,3-DBNQ (2,3-dibromo-1,4-naphthoquinone), which showed prominent antifungal activity (MIC of &lt;1.56 - 6.25 µg/mL) in all chosen test settings. However, its toxicity in MRC-5 cells (IC50 = 15.44 µM), a recorded 100% mortality in A. salina at a concentration of 50 µg/mL, as well as inhibition of 94.8% of the tomato seeds at a concentration of 400 µg/mL and inhibition of 64.1% of arugula seeds at a concentration of 200 µg/mL may limit hypothetical therapeutic applications. It was demonstrated that the likely mechanism of action of 2,3-DBNQ involves interfering with fungal membrane permeability, leading to increased leakage of nucleotides. This study adds to available knowledge on antifungal effects of naphthoquinones, especially of 2,3-DBNQ, against opportunistic yeasts and dermatophytes. However, the observed cytotoxicity in the MRC-5 cell lineage, A. salina, as well as tomato and arugula seeds highlights a need for further research to optimize the selectivity and safety profile of naphthoquinones like 2,3-DBNQ before potential clinical use may be assessed.

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Section: Discussionmentioning

confidence: 99%