Design and synthesis of caffeic acid derivatives and evaluation of their inhibitory activity against Pseudomonas aeruginosa

Zeng, Yun-feng; Su, Ya-lun; Liu, Weiliang; Chen, Hong-geng; Zeng, Shaogao; Zhou, Haibo; Chen, Weimin; Zheng, Junxia; Sun, Ping‐Hua

doi:10.1007/s00044-021-02810-w

Cited by 7 publications

(3 citation statements)

References 28 publications

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“…Referring to the methods mentioned in the literature [62], the ∆lasI∆rhlI mutant that showed the deficient ability to produce rhamnolipid and elastase was used as a positive control. A single colony of the test organism was selected and incubated overnight in 5 mL LB medium at a final OD 600 = 0.01.…”

Section: Pyocyanin Assaymentioning

confidence: 99%

Discovery of Melittin as Triple-Action Agent: Broad-Spectrum Antibacterial, Anti-Biofilm, and Potential Anti-Quorum Sensing Activities

Yang,

Ma,

Chen

et al. 2024

Molecules

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The development of antibiotic-resistant microorganisms is a major global health concern. Recently, there has been an increasing interest in antimicrobial peptides as a therapeutic option. This study aimed to evaluate the triple-action (broad-spectrum antibacterial, anti-biofilm, and anti-quorum sensing activities) of melittin, a membrane-active peptide present in bee venom. The minimum inhibitory concentration and minimum bactericidal concentration of the melittin were determined using the microdilution method and agar plate counting. Growth curve analysis revealed that melittin showed a concentration-dependent antibacterial activity. Scanning electron microscope analysis revealed that melittin treatment altered the morphology. Confocal laser scanning microscope revealed that melittin increased the membrane permeability and intracellular ROS generation in bacteria, all of which contribute to bacterial cell death. In addition, the crystal violet (CV) assay was used to test the anti-biofilm activity. The CV assay demonstrated that melittin inhibited biofilm formation and eradicated mature biofilms. Biofilm formation mediated by quorum sensing (QS) plays a major role in this regard, so molecular docking and molecular dynamics analysis confirmed that melittin interacts with LasR receptors through hydrogen bonds, and further evaluates the anti-QS activity of melittin through the production of virulence factors (pyocyanin, elastase, and rhamnolipid), exopolysaccharides secretion, and bacterial motility, that may be the key to inhibiting the biofilm formation mechanism. The present findings highlight the promising role of melittin as a broad-spectrum antibacterial, anti-biofilm agent, and potential QS inhibitor, providing a new perspective and theoretical basis for the development of alternative antibiotics.

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Section: Pyocyanin Assaymentioning

confidence: 99%

Discovery of Melittin as Triple-Action Agent: Broad-Spectrum Antibacterial, Anti-Biofilm, and Potential Anti-Quorum Sensing Activities

Yang,

Ma,

Chen

et al. 2024

Molecules

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“…It has also been proven that dihydrocaffeic acid reduced biofilm formation in P. aeruginosa PAO1. A biofilm inhibition rate of 19.82% was noted for DHCA, while caffeic acid and azithromycin (positive control) were observed to have rates of 22.67 and 35.31%, respectively [131]. The research on dihydrocaffeic acid was part of a larger study on the effects of natural substances on P. aeruginosa and other bacteria's growth and biofilm formation [132].…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Dihydrocaffeic Acid—Is It the Less Known but Equally Valuable Phenolic Acid?

Zieniuk

2023

Biomolecules

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Dihydrocaffeic acid (DHCA) is a phenolic acid bearing a catechol ring and three-carbon side chain. Despite its being found in minor amounts in numerous plants and fungi of different origins, it has attracted the interest of various research groups in many fields of science, from food to biomedical applications. The review article presented herein aims to show a wider audience the health benefits and therapeutic, industrial, and nutritional potential of dihydrocaffeic acid, by sheddinglight on its occurrence, biosynthesis, bioavailability, and metabolism. The scientific literature describes at least 70 different derivatives of dihydrocaffeic acid, both those occurring naturally and those obtained via chemical and enzymatic methods. Among the most frequently used enzymes that were applied for the modification of the parent DHCA structure, there are lipases that allow for obtaining esters and phenolidips, tyrosinases used for the formation of the catechol ring, and laccases to functionalize this phenolic acid. In many studies, both in vitro and in vivo, the protective effect of DHCA and its derivatives on cells subjected to oxidative stress and inflammation were acknowledged.

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“…It was found that a caffeic acid derivative with phenolic hydroxyl group 49 ( Figure 15 a) played the same role as amorfrutins B. It inhibits las and pqs as well and has favorable inhibition of the expression of virulence factors [ 111 ]. Through the research and exploration of Chinese herbal medicine, falcarindiol ( Figure 15 b), the main ingredient of Notopterygiumincisum , was found to have inhibitory effects on both las and pqs .…”

Section: Inhibitors Acting On Multiple Qs Systemsmentioning

confidence: 99%

The Molecular Architecture of Pseudomonas aeruginosa Quorum-Sensing Inhibitors

Shen

Wang

et al. 2022

Marine Drugs

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The survival selection pressure caused by antibiotic-mediated bactericidal and bacteriostatic activity is one of the important inducements for bacteria to develop drug resistance. Bacteria gain drug resistance through spontaneous mutation so as to achieve the goals of survival and reproduction. Quorum sensing (QS) is an intercellular communication system based on cell density that can regulate bacterial virulence and biofilm formation. The secretion of more than 30 virulence factors of P. aeruginosa is controlled by QS, and the formation and diffusion of biofilm is an important mechanism causing the multidrug resistance of P. aeruginosa, which is also closely related to the QS system. There are three main QS systems in P. aeruginosa: las system, rhl system, and pqs system. Quorum-sensing inhibitors (QSIs) can reduce the toxicity of bacteria without affecting the growth and enhance the sensitivity of bacterial biofilms to antibiotic treatment. These characteristics make QSIs a popular topic for research and development in the field of anti-infection. This paper reviews the research progress of the P. aeruginosa quorum-sensing system and QSIs, targeting three QS systems, which will provide help for the future research and development of novel quorum-sensing inhibitors.

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Design and synthesis of caffeic acid derivatives and evaluation of their inhibitory activity against Pseudomonas aeruginosa

Cited by 7 publications

References 28 publications

Discovery of Melittin as Triple-Action Agent: Broad-Spectrum Antibacterial, Anti-Biofilm, and Potential Anti-Quorum Sensing Activities

Discovery of Melittin as Triple-Action Agent: Broad-Spectrum Antibacterial, Anti-Biofilm, and Potential Anti-Quorum Sensing Activities

Dihydrocaffeic Acid—Is It the Less Known but Equally Valuable Phenolic Acid?

The Molecular Architecture of Pseudomonas aeruginosa Quorum-Sensing Inhibitors

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