Aloe emodin-conjugated sulfonyl hydrazones as novel type of antibacterial modulators against S. aureus 25923 through multifaceted synergistic effects

Deng, Zhao; Bheemanaboina, Rammohan R. Yadav; Luo, Yan; Zhou, Cheng‐He

doi:10.1016/j.bioorg.2022.106035

Cited by 37 publications

(15 citation statements)

References 64 publications

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“…The membrane impermeable dye propidium iodide (PI) can release a red fluorescence after entering damaged cell membranes and binding to DNA. − In order to explore inner membrane targeting capability of 3-(aminothiazolyl)quinolones, this study subsequently measured bacterial absorption efficiency of PI after treatment with compound 17a . The results in Figure S6A show that the PI uptake measurement increased with the increase of ATQ 17a .…”

Section: Results and Discussionmentioning

confidence: 99%

New Efforts toward Aminothiazolylquinolones with Multitargeting Antibacterial Potential

Zhang

Battini

et al. 2023

J. Agric. Food Chem.

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New antibacterial 3-(aminothiazolyl)quinolones (ATQs) were designed and efficiently synthesized to counteract the growing multidrug resistance in animal husbandry. Bioactive assays manifested that N,N-dicyclohexylaminocarbonyl ATQ 10e and methyl ATQ 17a, respectively, showed better antibacterial behavior against Staphylococcus aureus ATCC 29213 and Pseudomonas aeruginosa than reference drug norfloxacin. Notably, highly active ATQ 17a with low hemolysis, negligible mammalian cytotoxicity, and good pharmacokinetic properties displayed low trends to induce resistance and synergistic combinations with norfloxacin. Preliminary mechanism exploration implied that representative ATQ 17a could inhibit the formation of biofilms and destroy bacterial membrane integrity, further binding to intracellular DNA and DNA gyrase to hinder bacterial DNA replication. ATQ 17a could also induce the production of excess reactive oxygen species and reduce bacterial metabolism to accelerate bacterial death. These results provided a promise for 3-(aminothiazolyl)quinolones as new potential multitargeting antibacterial agents to treat bacterial infection of animals.

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Section: Results and Discussionmentioning

confidence: 99%

New Efforts toward Aminothiazolylquinolones with Multitargeting Antibacterial Potential

Zhang

Battini

et al. 2023

J. Agric. Food Chem.

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“…DiSC3(5) fluorescent dye can be absorbed by polarized cells and gathered in the phospholipid bilayer accompanied by fluorescence self-quenching. Once the membrane potential is disturbed, the dyes are released from cells and give off strong fluorescence, providing a manner to measure bacterial membrane potential [ 54 , 55 , 56 ]. As exhibited in Figure 7 , after incubation with different concentrations of coumarin 11f , the fluorescence intensity presented a dose-dependent increase, indicating that PHCI 11f could obviously dissipate the membrane potential and lead to membrane depolarization.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Evaluation of Piperazine Hybridized Coumarin Indolylcyanoenones with Antibacterial Potential

et al. 2023

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A class of piperazine hybridized coumarin indolylcyanoenones was exploited as new structural antibacterial frameworks to combat intractable bacterial resistance. Bioactive assessment discovered that 4-chlorobenzyl derivative 11f showed a prominent inhibition on Pseudomonas aeruginosa ATCC 27853 with a low MIC of 1 μg/mL, which was four-fold more effective than norfloxacin. Importantly, the highly active 11f with inconspicuous hemolysis towards human red blood cells displayed quite low proneness to trigger bacterial resistance. Preliminary explorations on its antibacterial behavior disclosed that 11f possessed the ability to destroy bacterial cell membrane, leading to increased permeability of inner and outer membranes, the depolarization and fracture of membrane, and the effusion of intracellular components. Furthermore, bacterial oxidative stress and metabolic turbulence aroused by 11f also accelerated bacterial apoptosis. In particular, 11f could not only effectively inset into DNA, but also bind with DNA gyrase through forming supramolecular complex, thereby affecting the biological function of DNA. The above findings of new piperazine hybridized coumarin indolylcyanoenones provided an inspired possibility for the treatment of resistant bacterial infections.

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“…Herein, the permeabilization effect of active OBMB- 6f on E. coli was evaluated using hydrophobic fluorescent probe NPN, which can emit strong fluorescence after entering the destabilized outer membrane . As shown in Figure S5, the fluorescence intensity of NPN in the E.…”

Section: Resultsmentioning

confidence: 99%

“…41 Herein, the permeabilization effect of active OBMB-6f on E. coli was evaluated using hydrophobic fluorescent probe NPN, which can emit strong fluorescence after entering the destabilized outer membrane. 42 As shown in Figure S5, the fluorescence intensity of NPN in the E. coli strain was greatly augmented with the concentrations of OBMB-6f increased, indicating that active OBMB-6f could enable permeabilization of the outer membrane of Gram-negative bacteria via a concentrationdependent pattern.…”

Section: Journal Of Agricultural and Foodmentioning

confidence: 86%

A New Discovery of Unique 13-(Benzimidazolylmethyl)berberines as Promising Broad-Spectrum Antibacterial Agents

Sun

Jeyakkumar

et al. 2022

J. Agric. Food Chem.

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A new hybridization of berberine and benzimidazoles was performed to produce 13-(benzimidazolylmethyl)berberines (BMB) as potentially broad-spectrum antibacterial agents with the hope of confronting multidrug-resistant bacterial infections in the livestock industry. Some of the newly prepared hybrids showed obvious antibacterial effects against tested strains. Particularly, 13-((1-octyl-benzimidazolyl)methyl)berberine 6f (OBMB-6f) was found to be the most promising compound that not only exerted a strong activity (MIC = 0.25–2 μg/mL) and low cytotoxicity but also possessed a fast bactericidal capacity and low propensity to develop resistance toward Staphylococcus aureus and Escherichia coli even after 26 serial passages. Moreover, OBMB-6f displayed the ability to prevent bacterial biofilm formation at low and high temperatures. The mechanistic exploration revealed that OBMB-6f could significantly disintegrate bacterial membranes, markedly facilitate intracellular ROS generation, and efficiently intercalate into DNA. These results provided a profound insight into BMB against multidrug-resistant bacterial infections in the livestock industry.

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Aloe emodin-conjugated sulfonyl hydrazones as novel type of antibacterial modulators against S. aureus 25923 through multifaceted synergistic effects

Cited by 37 publications

References 64 publications

New Efforts toward Aminothiazolylquinolones with Multitargeting Antibacterial Potential

New Efforts toward Aminothiazolylquinolones with Multitargeting Antibacterial Potential

Synthesis and Biological Evaluation of Piperazine Hybridized Coumarin Indolylcyanoenones with Antibacterial Potential

A New Discovery of Unique 13-(Benzimidazolylmethyl)berberines as Promising Broad-Spectrum Antibacterial Agents

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