Antibacterial activity and inhibition against Staphylococcus aureus NorA efflux pump by ferulic acid and its esterified derivatives

Pinheiro, Patrícia Gonçalves; Santiago, Gilvandete Maria Pinheiro; Silva, Francisco Erivaldo Freitas da; Araújo, Ana Carolina Justino de; Oliveira, Cícera Rejane Tavares de; Freitas, Priscilla Ramos; Rocha, Janaína Esmeraldo; Neto, José Bezerra de Araújo; Silva, Maria Milene Costa da; Tintino, Saulo Relison; Menezes, Irwin Rose Alencar de; Coutinho, Henrique Douglas Melo; Costa, José Galberto Martins da

doi:10.4103/2221-1691.321130

Cited by 18 publications

(3 citation statements)

References 41 publications

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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: 79%

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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Section: Antibacterial Activity Of the Habh And Cuhabh Complexesmentioning

confidence: 79%

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

et al. 2022

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“…Thus, it is not surprising that many efforts have been devoted to the development of FA derivatives [ 21 , 27 , 29 , 90 , 91 , 92 , 93 , 94 , 95 , 96 , 97 , 98 , 99 , 100 , 101 , 102 , 103 , 104 , 105 , 106 , 107 , 108 , 109 , 110 , 111 , 112 , 113 , 114 , 115 , 116 , 117 , 118 , 119 , 120 , 121 , 122 , 123 , 124 , 125 , 126 , 127 , 128 , 129 , 130 , 131 , 132 , 133 , 134 , 135 ]. Some of their relevant structural modifications and properties are summarized in Table 1 .…”

Section: Introductionmentioning

confidence: 99%

Rational Design of Multifunctional Ferulic Acid Derivatives Aimed for Alzheimer’s and Parkinson’s Diseases

et al. 2023

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Ferulic acid has numerous beneficial effects on human health, which are frequently attributed to its antioxidant behavior. In this report, many of them are reviewed, and 185 new ferulic acid derivatives are computationally designed using the CADMA-Chem protocol. Consequently, their chemical space was sampled and evaluated. To that purpose, selection and elimination scores were used, which are built from a set of descriptors accounting for ADME properties, toxicity, and synthetic accessibility. After the first screening, 12 derivatives were selected and further investigated. Their potential role as antioxidants was predicted from reactivity indexes directly related to the formal hydrogen atom transfer and the single electron transfer mechanisms. The best performing molecules were identified by comparisons with the parent molecule and two references: Trolox and α-tocopherol. Their potential as polygenic neuroprotectors was investigated through the interactions with enzymes directly related to the etiologies of Parkinson’s and Alzheimer’s diseases. These enzymes are acetylcholinesterase, catechol-O-methyltransferase, and monoamine oxidase B. Based on the obtained results, the most promising candidates (FA-26, FA-118, and FA-138) are proposed as multifunctional antioxidants with potential neuroprotective effects. The findings derived from this investigation are encouraging and might promote further investigations on these molecules.

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“…Various phytocompounds have been studied for its ability to inhibit S. aureus efflux pumps, including terpenes such as eugenol [17], carvacrol, thymol [18], estragole [19], α-pinene, and limonene [20]. Inhibition of NorA has also been reported for ferulic acid and its esterified derivatives [21], chalcones [22], and vitamin K3 [23]. On the other hand, various synthetic EPIs have been reported as efflux pump inhibitors [24][25][26].…”

Section: Introductionmentioning

confidence: 99%

Modulation of Drug Resistance by Furanochromones in NorA Overexpressing Staphylococcus Aureus

Rodrigues

Borges

Nogueira

et al. 2022

Evidence-Based Complementary and Alternative Medicine

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Khellin and visnagin are natural furanochromones that photoreact with DNA. Khellin has been used in the treatment of vitiligo and psoriasis, as well as in the treatment of angina pectoris and asthma due to its potent action as a coronary vasodilator and antispasmodic agent. The present study aimed to investigate whether the compounds khellin and visnagin act as inhibitors of NorA protein, an efflux pump overproduced by the strain of Staphylococcus aureus SA-1199B that confers resistance to the fluoroquinolones, such as norfloxacin and ciprofloxacin. These substances alone did not show antibacterial activity against the strain tested. On the other hand, when these compounds were added to the culture medium at subinhibitory concentration, they were able to reduce the minimum inhibitory concentration (MIC) of norfloxacin, ethidium bromide, as well as berberine, suggesting that these compounds are modulating agents of norfloxacin resistance, possibly due to NorA inhibition. Molecular docking analysis showed that both khellin and visnagin form hydrogen bonds with Arg310, an important residue in the interaction between NorA and its substrates, supporting the hypothesis that these compounds are NorA inhibitors. These results suggest a possible application of khellin and visnagin as adjuvants to norfloxacin in the treatment of infections caused by strains of S. aureus that overproduce NorA.

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Antibacterial activity and inhibition against Staphylococcus aureus NorA efflux pump by ferulic acid and its esterified derivatives

Cited by 18 publications

References 41 publications

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

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

Rational Design of Multifunctional Ferulic Acid Derivatives Aimed for Alzheimer’s and Parkinson’s Diseases

Modulation of Drug Resistance by Furanochromones in NorA Overexpressing Staphylococcus Aureus

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