Effect of hydroxyamines derived from lapachol and norlachol against Staphylococcus aureus strains carrying the NorA efflux pump

Figueredo, Fernando Gomes; Ramos, Ingrid T. L.; Paz, Josinete Angela da; Silva, Tania M. S.; Câmara, Celso A.; Oliveira-Tintino, Cícera Datiane de Morais; Tintino, Saulo Relison; Farias, Pablo Antonio Maia de; Menezes, Irwin Rose Alencar de; Coutinho, Henrique Douglas Melo; Fonteles, Marta Maria de França

doi:10.1016/j.meegid.2020.104370

Cited by 13 publications

(6 citation statements)

References 34 publications

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“…Menadione, a synthetic form of vitamin K 3 , significantly reduced the expression of NorA gene involved in the S. aureus efflux pump 33 . Various hydroxyamine compounds, derived from lapachol and norlachol have also been proven to inhibit NorA efflux pump in S. aureus 34 . Natural monocyclic sesquiterpene alcohol (α‐bisabolol) and its β‐cyclodextrin complex exhibited their inhibitory potential against TetK and NorA efflux pump of S. aureus .…”

Section: Discussionmentioning

confidence: 99%

Antibacterial potential of selected phytomolecules: An experimental study

Jhanji

Singh

Kumar

2021

Microbiology and Immunology

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Antibiotic resistance is a snowballing international threat. Some of the antibiotics have lost their effectiveness due to overuse and underuse. Thus, there is an urgent need to tackle this global challenge, either by inhibiting the resistance mechanisms or by the development of new chemical entities. Thus, in the current study, the antibacterial activity of selected phytomolecules was investigated against bacterial strains, alone and in combination, with standard drugs. The antibacterial potential of these phytomolecules was explored using in vitro assays (microtiter assay, bacterial growth kinetics, percentage retardation of growth, and antimicrobial synergy study) and in vivo studies (zebrafish infection model). In vitro and in vivo studies have shown promising antibacterial effects against, both, Gram‐positive and Gram‐negative bacteria. Moreover, a cell viability assay also indicated the cytoprotective effect of these phytomolecules in combination with standard antibiotics (SABX). Thus, these phytomolecules could be a promising broad‐spectrum antibacterial agent in combination with standard antibiotics.

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Section: Discussionmentioning

confidence: 99%

Antibacterial potential of selected phytomolecules: An experimental study

Jhanji

Singh

Kumar

2021

Microbiology and Immunology

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“…The efflux pump inhibition was assayed using a subinhibitory concentration of efflux pump standard inhibitors and tannic acid (MIC/8), observing their capacity to decrease the MIC of ethidium bromide and antibiotics due the possible inhibitory effect of these substances. In other studies, the effectiveness of inhibiting the efflux pump mechanism was also demonstrated in Staphylococcus aureus strains by caffeic and gallic acid (the MrsA pumps of the strain RN-4220 and NorA of the strain 1199B) [73], hydroxyamines derived from lapachol and norlachol (NorA pumps from the strain 1199B) [74], ferulic acid and its esterified derivatives (NorA pumps from the strain 1199B) [75]. In contrast, studies [76] have shown the activity of blocking the efflux pump by quercetin.…”

Section: Antibacterial Activity Of the Habh And Cuhabh Complexesmentioning

confidence: 80%

From the Physicochemical Characteristic of Novel Hesperetin Hydrazone to Its In Vitro Antimicrobial Aspects

et al. 2022

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Microorganisms are able to give rise to biofilm formation on food matrixes and along food industry infrastructures or medical equipment. This growth may be reduced by the application of molecules preventing bacterial adhesion on these surfaces. A new Schiff base ligand, derivative of hesperetin, HABH (2-amino-N′-(2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-ylidene)benzohydrazide), and its copper complex, CuHABH [CuLH2(OAc)], were designed, synthesized and analyzed in terms of their structure and physicochemical properties, and tested as antibacterial agents. Their structures both in a solid state and in solution were established using several methods: FT-IR, 1H NMR, 13C NMR, UV-Vis, FAB MS, EPR, ESI-MS and potentiometry. Coordination binding of the copper(II) complex dominating at the physiological pH region in the solution was found to be the same as that detected in the solid state. Furthermore, the interaction between the HABH and CuHABH with calf-thymus DNA (CT-DNA) were investigated. These interactions were tracked by UV-Vis, CD (circular dichroism) and spectrofluorimetry. The results indicate a stronger interaction of the CuHABH with the CT-DNA than the HABH. It can be assumed that the nature of the interactions is of the intercalating type, but in the high concentration range, the complex can bind to the DNA externally to phosphate residues or to a minor/major groove. The prepared compounds possess antibacterial and antibiofilm activities against Gram-positive and Gram-negative bacteria. Their antagonistic activity depends on the factor-strain test system. The glass was selected as a model surface for the experiments on antibiofilm activity. The adhesion of bacterial cells to the glass surface in the presence of the compounds was traced by luminometry and the best antiadhesive action against both bacterial strains was detected for the CuHABH complex. This molecule may play a crucial role in disrupting exopolymers (DNA/proteins) in biofilm formation and can be used to prevent bacterial adhesion especially on glass equipment.

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“…Therefore, the NorA pump and other efflux pumps are attractive targets to many studies [ 93 – 98 ]. The present study along with previous studies [ 93 – 98 ] showed that the potential antibacterial antibiofilm activities as well as the inhibited NorA efflux pump were because of the compounds' molecular docking mechanisms. The compounds' activity correlated with physicochemical properties, such as positive charge, aromatic ring, and hydrophobic interactions of the compounds with the efflux pump, which is mediated by hydrogen bonds.…”

Section: Resultsmentioning

confidence: 99%

Effect of New 2-Thioxoimidazolidin-4-one Compounds against Staphylococcus aureus Clinical Strains and Immunological Markers’ Combinations

Subhi

Fatah

Muhammad

2022

Canadian Journal of Infectious Diseases and Medical Microbiolog

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Although the structure-activity relationship indicates that the 4-thioxoimidazolidin ring is essential for antibacterial activities and pharmaceutical applications, there were no enough studies on the derivatives of this compound. Evaluating the new hydantoin compounds C5 (3-((2-bromobenzylidene) amino)-2- thioxoimidazolidin-4-one) and C6 (3-((4- methoxybenzylidene) amino)-2-thioxoimidazolidin-4-one) that were prepared against clinical Staphylococcus aureus isolates for antibacterial, antibiofilm, and antihemagglutination activities is the aim of this study. Therefore, the potential clinical resistance of the strains was evaluated by their ability to form biofilms, antibiotic resistance, and agglutinate erythrocytes macroscopically and microscopically; besides, the bacterial biofilm was screened for any association with the patient’s serum immunoglobulin levels and complements. Despite the effective concentration for C5 and C6 compounds, which is ≤ 31.25 μg/ml, the reduction rate is not concentration-dependent; it depends on the molecular docking of the hydantoin compounds. Hence, the effect of the minimal inhibitory concentrations (MICs) is variable. In this study, the results for the compounds (with the concentration of 31.25–62.5 μg/mL for C5 and 62.5–125 μg/mL for C6) significantly manifest the antibacteria, antibiofilm, and antihemagglutination effects against the virulent strains of S. aureus due to the high percentage of biofilm inhibition that was caused by the new hydantoin compounds. Besides, time-kill kinetics studies showed that these compounds pose bactericidal action. Overall, this study revealed that the new hydantoin derivatives have an interesting potential as new antibacterial drugs through the inhibition of bacterial adhesion. The infections of these isolates activate the complement system through the lectin pathway. Nevertheless, these compounds can be improved in order to be used at even lower concentrations.

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Effect of hydroxyamines derived from lapachol and norlachol against Staphylococcus aureus strains carrying the NorA efflux pump

Cited by 13 publications

References 34 publications

Antibacterial potential of selected phytomolecules: An experimental study

Antibacterial potential of selected phytomolecules: An experimental study

From the Physicochemical Characteristic of Novel Hesperetin Hydrazone to Its In Vitro Antimicrobial Aspects

Effect of New 2-Thioxoimidazolidin-4-one Compounds against Staphylococcus aureus Clinical Strains and Immunological Markers’ Combinations

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