Antimicrobial and biofilm inhibiting potential of an amide derivative [N-(2′, 4′-dinitrophenyl)-3β-hydroxyurs-12-en-28-carbonamide] of ursolic acid by modulating membrane potential and quorum sensing against colistin resistant Acinetobacter baumannii

Usmani, Yamina; Ahmed, Ayaz; Faizi, Shaheen; Versiani, Muhammad Ali; Shamshad, Shumaila; Khan, Saeed; Simjee, Shabana Usman

doi:10.1016/j.micpath.2021.104997

Cited by 24 publications

(11 citation statements)

References 40 publications

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“…In turn, this can result in differences in the ability to interact with LTA ( Figure S2 ) and to alter biophysical membrane properties. Further studies, including with ursolic derivatives [ 62 ], could be conducted to explore in more detail structure–activity relationships [ 60 , 63 , 64 ].…”

Section: Discussionmentioning

confidence: 99%

Effect of Ursolic and Oleanolic Acids on Lipid Membranes: Studies on MRSA and Models of Membranes

et al. 2021

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Staphylococcus aureus is an opportunistic pathogen and the major causative agent of life-threatening hospital- and community-acquired infections. A combination of antibiotics could be an opportunity to address the widespread emergence of antibiotic-resistant strains, including Methicillin-Resistant S. aureus (MRSA). We here investigated the potential synergy between ampicillin and plant-derived antibiotics (pentacyclic triterpenes, ursolic acid (UA) and oleanolic acid (OA)) towards MRSA (ATCC33591 and COL) and the mechanisms involved. We calculated the Fractional Inhibitory Concentration Index (FICI) and demonstrated synergy. We monitored fluorescence of Bodipy-TR-Cadaverin, propidium iodide and membrane potential-sensitive probe for determining the ability of UA and OA to bind to lipoteichoic acids (LTA), and to induce membrane permeabilization and depolarization, respectively. Both pentacyclic triterpenes were able to bind to LTA and to induce membrane permeabilization and depolarization in a dose-dependent fashion. These effects were not accompanied by significant changes in cellular concentration of pentacyclic triterpenes and/or ampicillin, suggesting an effect mediated through lipid membranes. We therefore focused on membranous effects induced by UA and OA, and we investigated on models of membranes, the role of specific lipids including phosphatidylglycerol and cardiolipin. The effect induced on membrane fluidity, permeability and ability to fuse were studied by determining changes in fluorescence anisotropy of DPH/generalized polarization of Laurdan, calcein release from liposomes, fluorescence dequenching of octadecyl-rhodamine B and liposome-size, respectively. Both UA and OA showed a dose-dependent effect with membrane rigidification, increase of membrane permeabilization and fusion. Except for the effect on membrane fluidity, the effect of UA was consistently higher compared with that obtained with OA, suggesting the role of methyl group position. All together the data demonstrated the potential role of compounds acting on lipid membranes for enhancing the activity of other antibiotics, like ampicillin and inducing synergy. Such combinations offer an opportunity to explore a larger antibiotic chemical space.

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Section: Discussionmentioning

confidence: 99%

Effect of Ursolic and Oleanolic Acids on Lipid Membranes: Studies on MRSA and Models of Membranes

et al. 2021

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“…Other approaches along with surface modifications have also been explored and focused mainly on compounds that interfere with QS by delivering signal blockers, hindering the production of functional bacterial adhesins, inducing biofilm detachment, and interfering with biofilm regulation mechanisms [ 28 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 ]. Figure 4 details the antimicrobial and more importantly antibiofilm agents and strategic approaches that are currently being explored in several studies to help control biofilm-associated SSIs.…”

Section: Novel Strategies To Control Biofilm-associated Ssismentioning

confidence: 99%

Biofilms in Surgical Site Infections: Recent Advances and Novel Prevention and Eradication Strategies

2022

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Surgical site infections (SSIs) are common postoperative occurrences due to contamination of the surgical wound or implanted medical devices with community or hospital-acquired microorganisms, as well as other endogenous opportunistic microbes. Despite numerous rules and guidelines applied to prevent these infections, SSI rates are considerably high, constituting a threat to the healthcare system in terms of morbidity, prolonged hospitalization, and death. Approximately 80% of human SSIs, including chronic wound infections, are related to biofilm-forming bacteria. Biofilm-associated SSIs are extremely difficult to treat with conventional antibiotics due to several tolerance mechanisms provided by the multidrug-resistant bacteria, usually arranged as polymicrobial communities. In this review, novel strategies to control, i.e., prevent and eradicate, biofilms in SSIs are presented and discussed, focusing mainly on two attractive approaches: the use of nanotechnology-based composites and natural plant-based products. An overview of new therapeutic agents and strategic approaches to control epidemic multidrug-resistant pathogenic microorganisms, particularly when biofilms are present, is provided alongside other combinatorial approaches as attempts to obtain synergistic effects with conventional antibiotics and restore their efficacy to treat biofilm-mediated SSIs. Some detection and real-time monitoring systems to improve biofilm control strategies and diagnosis of human infections are also discussed.

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“…Usmani et al [ 53 ] investigated the antimicrobial potential of UA and its various amide derivatives against nosocomial pathogen Acinetobacter baumannii ATCC 19606 and its clinical colistin-resistant strains. It is interesting that despite the lack of antibacterial properties of pure UA, the authors showed very good antibiofilm properties of one of its derivatives (3-β-N-(2′,4′-dinitrophenyl)-3-hydroxyurs-12-en28-amide) against all tested A. baumannii strains.…”

Section: The Mechanisms Of Antibacterial Activity Of Aa and Uamentioning

confidence: 99%

Anti-Planktonic and Anti-Biofilm Properties of Pentacyclic Triterpenes—Asiatic Acid and Ursolic Acid as Promising Antibacterial Future Pharmaceuticals

2022

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Due to the ever-increasing number of multidrug-resistant bacteria, research concerning plant-derived compounds with antimicrobial mechanisms of action has been conducted. Pentacyclic triterpenes, which have a broad spectrum of medicinal properties, are one of such groups. Asiatic acid (AA) and ursolic acid (UA), which belong to this group, exhibit diverse biological activities that include antioxidant, anti-inflammatory, diuretic, and immunostimulatory. Some of these articles usually contain only a short section describing the antibacterial effects of AA or UA. Therefore, our review article aims to provide the reader with a broader understanding of the activity of these acids against pathogenic bacteria. The bacteria in the human body can live in the planktonic form and create a biofilm structure. Therefore, we found it valuable to present the action of AA and UA on both planktonic and biofilm cultures. The article also presents mechanisms of the biological activity of these substances against microorganisms.

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Antimicrobial and biofilm inhibiting potential of an amide derivative [N-(2′, 4′-dinitrophenyl)-3β-hydroxyurs-12-en-28-carbonamide] of ursolic acid by modulating membrane potential and quorum sensing against colistin resistant Acinetobacter baumannii

Cited by 24 publications

References 40 publications

Effect of Ursolic and Oleanolic Acids on Lipid Membranes: Studies on MRSA and Models of Membranes

Effect of Ursolic and Oleanolic Acids on Lipid Membranes: Studies on MRSA and Models of Membranes

Biofilms in Surgical Site Infections: Recent Advances and Novel Prevention and Eradication Strategies

Anti-Planktonic and Anti-Biofilm Properties of Pentacyclic Triterpenes—Asiatic Acid and Ursolic Acid as Promising Antibacterial Future Pharmaceuticals

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