Membrane-damage antibacterial mechanism of phenanthrene compounds from Arundina graminifolia (D.Don) Hochr

Zhang, Xingyu; Qiu, Yourou; Du, Yimei; Chen, Yan; Liu, Meifeng

doi:10.1016/j.sajb.2022.11.018

Cited by 8 publications

(2 citation statements)

References 30 publications

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“…Imidazole derivatives have widely reported antimicrobial activity, including some commercially available products like metronidazole, tinidazole, econazole, and clotrimazole (Figure ), − where benzimidazole and dibenzimidazole are important antibacterial parent nucleus structures, and have been used in developing new antimicrobials . Moreover, phenanthroline derivatives from natural sources showed significant antimicrobial potential; − the stable tricyclic structure can provide ideal hydrophobicity. Therefore, our research particularly focuses on hydrophobic phenanthroimidazole compounds, a class of rigid and conjugated planar structures with fluorescent activity which has not been extensively studied for their antimicrobial activities yet (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Development of Membrane-Targeting Fluorescent 2-Phenyl-1H-phenanthro[9,10-d]imidazole-Antimicrobial Peptide Mimic Conjugates against Methicillin-Resistant Staphylococcus aureus

Xu,

Yan,

Kang

et al. 2024

J. Med. Chem.

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The escalation of multidrug-resistant bacterial infections, especially infections caused by methicillin-resistant Staphylococcus aureus (MRSA), underscores the urgent need for novel antimicrobial drugs. Here, we synthesized a series of amphiphilic 2phenyl-1H-phenanthro [9,10-d]imidazole-antimicrobial peptide (AMP) mimic conjugates (III1−30). Among them, compound III13 exhibited excellent antibacterial activity against G+ bacteria and clinical MRSA isolates (MIC = 0.5−2 μg/mL), high membrane selectivity, and low toxicity. Additionally, compared with traditional clinical antibiotics, III13 demonstrated rapid bactericidal efficacy and was less susceptible to causing bacterial resistance. Mechanistic studies revealed that III13 targets phosphatidylglycerol (PG) on bacterial membranes to disrupt membrane integrity, leading to an increase in intracellular ROS and leakage of proteins and DNA, ultimately causing bacterial cell death. Furthermore, III13 possessed good fluorescence properties with potential for further dynamic monitoring of the antimicrobial process. Notably, III13 showed better in vivo efficacy against MRSA compared to vancomycin, suggesting its potential as a promising candidate for anti-MRSA medication.

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Section: Introductionmentioning

confidence: 99%

Development of Membrane-Targeting Fluorescent 2-Phenyl-1H-phenanthro[9,10-d]imidazole-Antimicrobial Peptide Mimic Conjugates against Methicillin-Resistant Staphylococcus aureus

Xu,

Yan,

Kang

et al. 2024

J. Med. Chem.

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“…Unlike conventional antibiotics, AMPs exhibit high specificity by targeting specific bacterial elements such as phosphatidylglycerol (PG), which accumulate on the bacterial surface through electrostatic interactions and disrupt membrane stability and integrity (Zhang and Gallo, 2016). In addition, natural products represent a valuable library of compounds, and many potent and unique mechanisms of small molecule antimicrobial drugs are derived from endogenous antimicrobial metabolites of plants (Yoshikawa et al, 2012;Qian et al, 2015;Tagare and Vaidyanathan, 2018;Tóth et al, 2018;Yan et al, 2018;Zhang et al, 2022). Our group previously created a series of AMP mimetics using magnolol, a bioactive compound from Magnolia officinalis identified to have initial antimicrobial activity, as the core structure through a modular assembly strategy, overcoming its poor water solubility and high biotoxicity (Guo et al, 2021a).…”

Section: Introductionmentioning

confidence: 99%

A membrane-targeting magnolol derivative for the treatment of methicillin-resistant Staphylococcus aureus infections

Zhang,

Fang,

Zhao

et al. 2024

Front. Microbiol.

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Multidrug-resistant bacterial infections are a major global health challenge, especially the emergence and rapid spread of methicillin-resistant Staphylococcus aureus (MRSA) urgently require alternative treatment options. Our study has identified that a magnolol derivative 6i as a promising agent with significant antibacterial activity against S. aureus and clinical MRSA isolates (MIC = 2–8 μg/mL), showing high membrane selectivity. Unlike traditional antibiotics, 6i demonstrated rapid bactericidal efficiency and a lower propensity for inducing bacterial resistance. Compound 6i also could inhibit biofilm formation and eradicate bacteria within biofilms. Mechanistic studies further revealed that 6i could target bacterial cell membranes, disrupting the integrity of the cell membrane and leading to increased DNA leakage, resulting in potent antibacterial effects. Meanwhile, 6i also showed good plasma stability and excellent biosafety. Notably, 6i displayed good in vivo antibacterial activity in a mouse skin abscess model of MRSA-16 infection, which was comparable to the positive control vancomycin. These findings indicated that the magnolol derivative 6i possessed the potential to be a novel anti-MRSA infection agent.

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Characterization, in-vitro digestion, antioxidant, anti-hyperlipidemic and antibacterial activities of Zanthoxylum bungeanum Maxim essential oil nano-emulsion

Li,

Chen,

Zeng

et al. 2023

Food Bioscience

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Membrane-damage antibacterial mechanism of phenanthrene compounds from Arundina graminifolia (D.Don) Hochr

Cited by 8 publications

References 30 publications

Development of Membrane-Targeting Fluorescent 2-Phenyl-1H-phenanthro[9,10-d]imidazole-Antimicrobial Peptide Mimic Conjugates against Methicillin-Resistant Staphylococcus aureus

Development of Membrane-Targeting Fluorescent 2-Phenyl-1H-phenanthro[9,10-d]imidazole-Antimicrobial Peptide Mimic Conjugates against Methicillin-Resistant Staphylococcus aureus

A membrane-targeting magnolol derivative for the treatment of methicillin-resistant Staphylococcus aureus infections

Characterization, in-vitro digestion, antioxidant, anti-hyperlipidemic and antibacterial activities of Zanthoxylum bungeanum Maxim essential oil nano-emulsion

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