Multi-Hydrogen Bonding on Quaternized-Oligourea Receptor Facilitated Its Interaction with Bacterial Cell Membranes and DNA for Broad-Spectrum Bacteria Killing

Herein, we report a new strategy for the design of antibiotic agents based on the electrostatic interaction and hydrogen bonding, highlighting the significance of hydrogen bonding and the increased recognition sites in facilitating the interaction with bacterial cell membranes and DNA. A series of q...

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Published inMolecules (Basel, Switzerland) Vol. 29; no. 16; p. 3937
Main Authors Yan, Xiaojin, Yang, Fan, Lv, Guanghao, Qiu, Yuping, Jia, Xiaoying, Hu, Qirong, Zhang, Jia, Yang, Jing, Ouyang, Xiangyuan, Gao, Lingyan, Jia, Chuandong
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.08.2024
MDPI
Subjects
anion receptor
Antibiotics
Bacteria
Bacterial genetics
Binding sites
Cell death
Deoxyribonucleic acid
DNA
DNA cleavage
Drug resistance in microorganisms
E coli
Ethylenediaminetetraacetic acid
host–guest systems
Hydrogen
Hydrogen bonding
Hydrogen bonds
Membranes
Morphology
Permeability
Scanning electron microscopy
supramolecular chemistry
Transmission electron microscopy
Japan
China
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Summary:Herein, we report a new strategy for the design of antibiotic agents based on the electrostatic interaction and hydrogen bonding, highlighting the significance of hydrogen bonding and the increased recognition sites in facilitating the interaction with bacterial cell membranes and DNA. A series of quaternary ammonium functionalized urea-based anion receptors were studied. While the monodentate mono-urea M1, bisurea M2, and trisurea M3 failed to break through the cell membrane barrier and thus could not kill bacteria, the extended bidentate dimers D1–D3 presented gradually increased membrane penetrating capabilities, DNA conformation perturbation abilities, and broad-spectrum antibacterial activities against E. coli, P. aeruginosa, S. aureus, E. faecalis, and S. epidermidis.
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These authors contributed equally to this work.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules29163937