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Article

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

1
Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi’an 710069, China
2
Shaanxi Key Laboratory of Degradable Biomedical Materials, Shaanxi R&D Center of Biomaterials and Fermentation Engineering, School of Chemical Engineering, Northwest University, Xi’an 710069, China
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Molecules 2024, 29(16), 3937; https://doi.org/10.3390/molecules29163937
Submission received: 30 July 2024 / Revised: 18 August 2024 / Accepted: 19 August 2024 / Published: 21 August 2024
(This article belongs to the Special Issue Host–Guest Inclusion Complexes and Their Miscellaneous Applications)

Abstract

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 D1D3 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.
Keywords: supramolecular chemistry; hydrogen bonds; anion receptor; host–guest systems; DNA cleavage supramolecular chemistry; hydrogen bonds; anion receptor; host–guest systems; DNA cleavage
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MDPI and ACS Style

Yan, X.; Yang, F.; Lv, G.; Qiu, Y.; Jia, X.; Hu, Q.; Zhang, J.; Yang, J.; Ouyang, X.; Gao, L.; et al. Multi-Hydrogen Bonding on Quaternized-Oligourea Receptor Facilitated Its Interaction with Bacterial Cell Membranes and DNA for Broad-Spectrum Bacteria Killing. Molecules 2024, 29, 3937. https://doi.org/10.3390/molecules29163937

AMA Style

Yan X, Yang F, Lv G, Qiu Y, Jia X, Hu Q, Zhang J, Yang J, Ouyang X, Gao L, et al. Multi-Hydrogen Bonding on Quaternized-Oligourea Receptor Facilitated Its Interaction with Bacterial Cell Membranes and DNA for Broad-Spectrum Bacteria Killing. Molecules. 2024; 29(16):3937. https://doi.org/10.3390/molecules29163937

Chicago/Turabian Style

Yan, Xiaojin, Fan Yang, Guanghao Lv, Yuping Qiu, Xiaoying Jia, Qirong Hu, Jia Zhang, Jing Yang, Xiangyuan Ouyang, Lingyan Gao, and et al. 2024. "Multi-Hydrogen Bonding on Quaternized-Oligourea Receptor Facilitated Its Interaction with Bacterial Cell Membranes and DNA for Broad-Spectrum Bacteria Killing" Molecules 29, no. 16: 3937. https://doi.org/10.3390/molecules29163937

APA Style

Yan, X., Yang, F., Lv, G., Qiu, Y., Jia, X., Hu, Q., Zhang, J., Yang, J., Ouyang, X., Gao, L., & Jia, C. (2024). Multi-Hydrogen Bonding on Quaternized-Oligourea Receptor Facilitated Its Interaction with Bacterial Cell Membranes and DNA for Broad-Spectrum Bacteria Killing. Molecules, 29(16), 3937. https://doi.org/10.3390/molecules29163937

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