An overview on the antibacterial properties of juglone, naphthazarin, plumbagin and lawsone derivatives and their metal complexes

Majdi, Chaimae; Duvauchelle, Valentin; Meffre, Patrick; Benfodda, Zohra

doi:10.1016/j.biopha.2023.114690

Cited by 12 publications

(3 citation statements)

References 76 publications

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“…The bidentate (O, O) and anionic coordination modes have limited literature for Cu(I) complexes [29], making this research an important report for this type of coordination to the metal center. However, for other metal centers, including Cu(II) complexes, the bidentate (O, O) coordination is commonly described in the literature [36][37][38][41][42][43]. The region between 1640 and 1680 cm −1 displays intense vibrational modes for naphthoquinone ligands, corresponding to the ν(C1=O1) and ν(C4=O3) stretching.…”

Section: Structural Studiesmentioning

confidence: 99%

Copper(I)/Triphenylphosphine Complexes Containing Naphthoquinone Ligands as Potential Anticancer Agents

Leite,

Araujo-Neto,

Guedes

et al. 2023

Inorganics

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Four new Cu/PPh3/naphtoquinone complexes were synthesized, characterized (IR, UV/visible, 1D/2D NMR, mass spectrometry, elemental analysis, and X-ray diffraction), and evaluated as anticancer agents. We also investigated the reactive oxygen species (ROS) generation capacity of complex 4, considering the well-established photochemical property of naphthoquinones. Therefore, employing the electron paramagnetic resonance (EPR) “spin trap”, 5,5-dimethyl-1-pyrroline N-oxide (DMPO) technique, we identified the formation of the characteristic •OOH species (hydroperoxyl radical) adduct even before irradiating the solution containing complex 4. As the irradiation progressed, this radical species gradually diminished, primarily giving rise to a novel species known as •DMPO-OH (DMPO + •OH radical). These findings strongly suggest that Cu(I)/PPh3/naphthoquinone complexes can generate ROS, even in the absence of irradiation, potentially intensifying their cytotoxic effect on tumor cells. Interpretation of the in vitro cytotoxicity data of the Cu(I) complexes considered their stability in cell culture medium. All of the complexes were cytotoxic to the lung (A549) and breast tumor cell lines (MDA-MB-231 and MCF-7). However, the higher toxicity for the lung (MRC5) and breast (MCF-10A) non-tumoral cells resulted in a low selectivity index. The morphological analysis of MDA-MB-231 cells treated with the complexes showed that they could cause decreased cell density, loss of cell morphology, and loss of cell adhesion, mainly with concentrations higher than the inhibitory concentration of 50% of cell viability (IC50) values. Similarly, the clonogenic survivance of these cells was affected only with concentrations higher than the IC50 values. An antimigratory effect was observed for complexes 1 and 4, showing around 20–40% of inhibition of wound closure in the wound healing experiments.

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Section: Structural Studiesmentioning

confidence: 99%

Copper(I)/Triphenylphosphine Complexes Containing Naphthoquinone Ligands as Potential Anticancer Agents

Leite,

Araujo-Neto,

Guedes

et al. 2023

Inorganics

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“…Although not true for Lawson itself, further substituted naphthoquinones, namely, naphthazarines, 27 for which we considered similar keratinophilic features, have been reported to generate ROS upon irradiation. 22,28,29 By screening the dedicated set of initial compounds, we were in fact able to identify promising PDT-keratin suitable naphthazarin candidates with absorption maxima around 500 nm wavelength (determined in aqueous media) and interesting biological activities against the pathogens T. rubrum and C. albicans (Table 1), thus meeting the mentioned criteria.…”

Section: ■ Introductionmentioning

confidence: 99%

Novel Henna-Related Naphthazarine Photosensitizers for an Effective Photodynamic Therapy of Onychomycosis

Baier,

Jansen,

Wenzel-Storjohann

et al. 2023

ACS Pharmacol. Transl. Sci.

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“…Juglone (5-hidroxy-1,4-naphthoquinone) is obtained from the walnut (Juglans regia L.) tree and has antibacterial and antifungal properties. Other naphthoquinone derivatives bind to specific receptors on cancer cells, and other derivatives have been investigated for their activity against bacteria and fungi [1][2][3][4][5][6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone Derivatives

Leyva,

Loredo-Carrillo,

Aguilar

2023

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Nitrated products are important since they are intermediates in the synthesis of other compounds, such as explosives, perfumes, dyes and plastics, among others, and they have an easy capacity to convert into other functional groups. The synthesis of compounds with biological activity that have a nitro group in their structure is relevant to improving and/or enhancing their effect. In this work, different methodologies for the nitration of naphthoquinone derivative compounds are presented. The nitration of 3-R-2-(phenylamino)-1,4-naphthoquinone derivatives was carried out with nitric acid and sulfuric acid; milder reaction conditions were also established by diluting the acids or performing the reaction with weaker acids. Other methodologies were tested using nitrate salts for mononitrate product synthesis. We used a solvent-free reaction with oxalic acid using 3-R-2-(phenylamino)-1,4-naphthoquinones (R=H, Br or Cl), noting that the electronegativity of the chlorine group is decisive for achieving nitration with good yields. Finally, a Michael addition was performed with some nitrated anilines. To obtain denitrated compounds in the ortho and para positions, the reaction with strong acids is feasible; however, for the formation of mononitrated products, the Michael-type addition is more convenient.

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An overview on the antibacterial properties of juglone, naphthazarin, plumbagin and lawsone derivatives and their metal complexes

Cited by 12 publications

References 76 publications

Copper(I)/Triphenylphosphine Complexes Containing Naphthoquinone Ligands as Potential Anticancer Agents

Copper(I)/Triphenylphosphine Complexes Containing Naphthoquinone Ligands as Potential Anticancer Agents

Novel Henna-Related Naphthazarine Photosensitizers for an Effective Photodynamic Therapy of Onychomycosis

Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone Derivatives

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