Synthetic Channel Specifically Inserts into the Lipid Bilayer of Gram‐Positive Bacteria but not that of Mammalian Erythrocytes

Zhang, Min; Zhu, Pingping; Xin, Pengyang; Wen, Shi Wu; Li, Zhan‐Ting; Hou, Jun‐Li

doi:10.1002/ange.201612093

Cited by 27 publications

(2 citation statements)

References 46 publications

(22 reference statements)

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“…8 For example, a peripheral acetylated mannosyl moieties-functionalized pillar [5]arene showed antiadhesion activity against uropathogenic Escherichia coli. 9 Not only pillar [5]arenes with incorpo-rated peptides, 10 phosphonium or ammonium, 11 guanidinium groups 12 but zwitterionic pillar [5]arenes 8 have also shown their unique antibacterial or antibiofilm activities. These results indicated that pillararene might be a useful scaffold for the construction of new antibacterial agents.…”

Section: ■ Introductionmentioning

confidence: 99%

Antibacterial and Antibiofilm Formation Activities of Pyridinium-Based Cationic Pillar[5]arene Against Pseudomonas aeruginosa

Yang

Zhao

Lian

et al. 2021

J. Agric. Food Chem.

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An omnipresent pathogenic bacterium, Pseudomonas aeruginosa (P. aeruginosa PAO1), is easy to contaminate environmental water or foods, causing daily food spoilage and infections. The biofilm-forming ability and bacterial resistance of P. aeruginosa PAO1 make it difficult to be eradicated by traditional bacteriostatic agents. In this work, we designed and synthesized a pyridinium-based pillar[5]arene (PP5), while trimethylammonium-based pillar[5]arene (TP5) was used as a control compound. After clear characterization, the antibacterial and antibiofilm activities as well as the microbial resistance of TP5 and PP5 against P. aeruginosa PAO1 were extensively examined. It was revealed that PP5 exhibited good inhibition activity with the minimum inhibitory concentration (MIC) of 0.051 mmol/L, while no significant antibacterial and biofilm formation activity for TP5 against P. aeruginosa PAO1 was observed. More importantly, PP5 had negligible antimicrobial resistance even after 18th passages. A transmission electron microscope (TEM) showed that PP5 could physically disrupt the cell membranes, causing the leakage of internal constituents, which is possibly ascribed to the synergistic penetrability and π−π interactions of strain, thus greatly reduced the development of bacterial resistance. Overall, the presented studies indicated that pyridinium moieties could facilitate the cationic pillar[5]arene to generate surprising antibacterial and antibiofilm formation ability against P. aeruginosa PAO1.

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Section: ■ Introductionmentioning

confidence: 99%

Antibacterial and Antibiofilm Formation Activities of Pyridinium-Based Cationic Pillar[5]arene Against Pseudomonas aeruginosa

Yang

Zhao

Lian

et al. 2021

J. Agric. Food Chem.

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“…Actually, since the mechanism of action does not rely on metabolic pathways, the tube proved active and selective for Methicillin-resistant Staphylococcus aureus (MRSA) with very low toxicity for mammalian cells. [60] Despite anionophores have been less studied than cationophores, the development of small-molecule anion transporters has increased in the last years. [61] Tomich and co-workers focused on the use of short peptides as chloride channels.…”

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confidence: 99%

Sensing, Transport and Other Potential Biomedical Applications of Pseudopeptides

Faggi

Luis

Alfonso

2019

CMC

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Pseudopeptides are privileged synthetic molecules built from the designed combination of peptide-like and abiotic artificial moieties. Consequently, they are benefited from the advantages of both families of chemical structures: modular synthesis, chemical and functional diversity, tailored three-dimensional structure, usually high stability in biological media and low non-specific toxicity. Accordingly, in the last years, these compounds have been used for different biomedical applications, ranging from bio-sensing, ion transport, the molecular recognition of biologically relevant species, drug delivery or gene transfection. This review highlights a selection of the most remarkable and recent advances in this field.

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Construction of π‐Surface‐Metalated Pillar[5]arenes which Bind Anions via Anion–π Interactions

Yang

Jiang²,

Wang³

et al. 2017

Angewandte Chemie

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By simple ligand exchange of the cationic transitionmetal complexes [(Cp*)M(acetone) 3 ](OTf) 2 (Cp* = pentamethylcyclopentadienyl and M = Ir or Rh) with pillar[5]arene, mono-and polynuclear pillar[5]arenes,anew class of metalated host molecules,i sp repared. Single-crystal X-ray analysis shows that the charged transition-metal cations are directly bound to the outer p-surface of aromatic rings of pillar[5]arene.O ne of the triflate anions is deeply embedded within the cavity of the trinuclear pillar[5]arenes,w hichi s different to the host-guest behavior of most pillar[5]arenes. DFT calculation of the electrostatic potential revealed that the metalated pillar[5]arenes featured an electron-deficient cavity due to the presence of the electron-withdrawing transition metals,t hus allowing encapsulation of electron-richg uests mainly driven by anion-p interactions.

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Synthetic Channel Specifically Inserts into the Lipid Bilayer of Gram‐Positive Bacteria but not that of Mammalian Erythrocytes

Cited by 27 publications

References 46 publications

Antibacterial and Antibiofilm Formation Activities of Pyridinium-Based Cationic Pillar[5]arene Against Pseudomonas aeruginosa

Antibacterial and Antibiofilm Formation Activities of Pyridinium-Based Cationic Pillar[5]arene Against Pseudomonas aeruginosa

Sensing, Transport and Other Potential Biomedical Applications of Pseudopeptides

Construction of π‐Surface‐Metalated Pillar[5]arenes which Bind Anions via Anion–π Interactions

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