Searching for a potential antibacterial lead structure against bacterial biofilms among new naphthoquinone compounds

Moreira, Caroline S.; Silva, A.C.J.A.; Novais, Juliana S.; Figueiredo, Agnes Marie Sá; Ferreira, Vı́tor F.; Rocha, David R. da; Castro, Helena C.

doi:10.1111/jam.13369

Cited by 28 publications

(16 citation statements)

References 66 publications

(101 reference statements)

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“…Droserone, 3-chloroplumbagin, plumbagin, and its isomer ramentaceone ( Figure 1 ) are the most prevalent naphthoquinones synthesized in tissues of plants of the Droseraceae family ( Juniper et al, 1989 ; Kreher et al, 1990 ; Gaascht et al, 2013 ; Krychowiak et al, 2014 ). The antibacterial activity of most of NQs concerns mainly Gram-positive bacteria like S. aureus , as most of Gram-negative bacteria are intrinsically resistant to NQs ( Riffel et al, 2002 ; Krolicka et al, 2008 , 2009 ; Moreira et al, 2017 ).…”

Section: Introductionmentioning

confidence: 99%

Silver Nanoparticles Combined With Naphthoquinones as an Effective Synergistic Strategy Against Staphylococcus aureus

et al. 2018

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Staphylococcus aureus is a human pathogen responsible for many antibiotic-resistant infections, for instance burn wound infections, which pose a threat to human life. Exploring possible synergy between various antimicrobial agents, like nanoparticles and plant natural products, may provide new weapons to combat antibiotic resistant pathogens. The objective of this study was to examine the potential of silver nanoparticles (AgNPs) to enhance the antimicrobial activity of selected naphthoquinones (NQs): plumbagin (PL), ramentaceone (RAM), droserone (DR), and 3-chloroplumbagin (3ChPL). We also attempted to elucidate the mechanism by which the AgNPs enhance the antimicrobial activity of NQs. We analyzed the interaction of AgNPs with bacterial membrane and its effect on membrane stability (TEM analysis, staining with SYTO9 and propidium iodide), as well as aggregation of NQs on the surface of nanoparticles (UV-Vis spectroscopy and DLS analysis). Our results demonstrated clearly a synergistic activity of AgNPs and three out of four tested NQs (FBC indexes ≤ 0.375). This resulted in an increase in their combined bactericidal effect toward the S. aureus reference strain and the clinical isolates, which varied in resistance profiles. The synergistic effect (FBC index = 0.375) resulting from combining 3ChPL with silver nitrate used as a control, emphasized the role of the ionic form of silver released from nanoparticles in their bactericidal activity in combination with NQs. The role of membrane damage and AgNPs-NQ interactions in the observed synergy of silver nanoparticles and NQs was also confirmed. Moreover, the described approach, based on the synergistic interaction between the above mentioned agents enables a reduction of their effective doses, thus significantly reducing cytotoxic effect of NQs toward eukaryotic HaCaT cells. Therefore, the present study on the use of a combination of agents (AgNPs-NQs) suggests its potential use as a possible strategy to combat antibiotic-resistant S. aureus.

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Section: Introductionmentioning

confidence: 99%

Silver Nanoparticles Combined With Naphthoquinones as an Effective Synergistic Strategy Against Staphylococcus aureus

et al. 2018

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“…A theoretical study of the relationship between the electronic structure and the activity of the P2X7R receptor from a series of 2-hydroxy-1,4-naphthoquinone derivatives, using the quantitative structure-activity relationship (QSAR) method was done. 52) The results showed that there are specific zones of these naphthoquinone derivatives potentially involved in the biological process. The presence of the different substituents seems not to have direct participation in the interaction; their importance may be associated with the modification of the electronic structure of the common skeleton.…”

Section: Cardioprotective and Anti-ischemic Propertiesmentioning

confidence: 96%

“…Based on the analysis of the results, a corresponding two-dimensional pharmacophore was proposed. 51,52) 2.5. Antimicrobial Activity There are on-going studies on the antimicrobial activity of 1,4-naphthoquinones in relation to various microbial pathogens that are dangerous as sources of fatal diseases, epidemics and nosocomial infections.…”

Section: Cardioprotective and Anti-ischemic Propertiesmentioning

confidence: 99%

1,4-Naphthoquinones: Some Biological Properties and Application

2020

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Over the past decade, a number of new 1,4-naphthoquinones have been isolated from natural sources and new 1,4-naphthoquinones with diverse structural features have been synthesized. Cardioprotective, antiischemic, hepatoprotective, neuroprotective and some other new properties were found for these compounds; their role in protecting against neurodegenerative diseases has been established. Their anti-inflammatory, antimicrobial and antitumor activities have been studied in more detail; new, previously unknown intracellular molecular targets and mechanisms of action have been discovered. Some compounds of this class are already being used as a medicinal drugs and some substances can be used as biochemical tools and probes for non-invasive detection of pathological areas in cells and tissues in myocardial infarction and neurodegenerative diseases using modern molecular imaging techniques.

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“…The antibacterial activity of 6a and its derivatives 7a, 7b, and 7c was tested as previously described using paper disks impregnated with each compound 13 . The derivatives were also analyzed quantitatively using microdilution assays in 96-well inert polystyrene microtiter plates (Nuclon; Nalge Nunc International, Rochester, NY, USA) to determine the minimal inhibitory concentration (MIC) 14 .…”

Section: Susceptibility Testsmentioning

confidence: 99%

Antibiofilm effects of N,O-acetals derived from 2-amino-1,4-naphthoquinone are associated with downregulation of important global virulence regulators in methicillin-resistant Staphylococcus aureus

Novais

Carvalho

Ramundo

et al. 2020

Sci Rep

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Despite the existing antibiotics, antimicrobial resistance is a major challenge. Consequently, the development of new drugs remains in great demand. Quinones is part of a broad group of molecules that present antibacterial activity besides other biological properties. The main purpose of this study was to evaluate the antibiofilm activities of synthetic N,O-acetals derived from 2-amino-1,4-naphthoquinone [7a: 2-(methoxymethyl)-amino-1,4-naphthoquinone; 7b: 2-(ethoxymethyl)-amino-1,4-naphthoquinone; and 7c: 2-(propynyloxymethyl)-amino-1,4-naphthoquinone] against methicillin-resistant Staphylococcus aureus (MRSA). The derivatives 7b and 7c, specially 7b, caused strong impact on biofilm accumulation. This inhibition was linked to decreased expression of the genes fnbA, spa, hla and psmα3. More importantly, this downregulation was paralleled by the modulation of global virulence regulators. The substitution of 2-ethoxymethyl (7b) in comparison with 2-propynyloxymethyl (7c) enhanced sarA-agr inhibition, decreased fnbA transcripts (positively regulated by sarA) and strongly impaired biofilm accumulation. Indeed, 7b triggered intensive autolysis and was able to eliminate vancomycin-persistent cells. Consequently, 7b is a promising molecule displaying not only antimicrobial effects, but also antibiofilm and antipersistence activities. Therefore, 7b is a good candidate for further studies involving the development of novel and more rational antimicrobials able to act in chronic and recalcitrant infections, associated with biofilm formation.

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Searching for a potential antibacterial lead structure against bacterial biofilms among new naphthoquinone compounds

Cited by 28 publications

References 66 publications

Silver Nanoparticles Combined With Naphthoquinones as an Effective Synergistic Strategy Against Staphylococcus aureus

Silver Nanoparticles Combined With Naphthoquinones as an Effective Synergistic Strategy Against Staphylococcus aureus

1,4-Naphthoquinones: Some Biological Properties and Application

Antibiofilm effects of N,O-acetals derived from 2-amino-1,4-naphthoquinone are associated with downregulation of important global virulence regulators in methicillin-resistant Staphylococcus aureus

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