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Issue 22, 2015
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Synthesis and evaluation of cationic norbornanes as peptidomimetic antibacterial agents

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Abstract

A series of structurally amphiphilic biscationic norbornanes have been synthesised as rigidified, low molecular weight peptidomimetics of cationic antimicrobial peptides. A variety of charged hydrophilic functionalities were attached to the norbornane scaffold including aminium, guanidinium, imidazolium and pyridinium moieties. Additionally, a range of hydrophobic groups of differing sizes were incorporated through an acetal linkage. The compounds were evaluated for antibacterial activity against both Gram-negative and Gram-positive bacteria. Activity was observed across the series; the most potent of which exhibited an MIC's ≤ 1 μg mL−1 against Streptococcus pneumoniae, Enterococcus faecalis and several strains of Staphylococcus aureus, including multi-resistant methicillin resistant (mMRSA), glycopeptide-intermediate (GISA) and vancomycin-intermediate (VISA) S. aureus.

Graphical abstract: Synthesis and evaluation of cationic norbornanes as peptidomimetic antibacterial agents

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Publication details

The article was received on 30 Mar 2015, accepted on 27 Apr 2015 and first published on 27 Apr 2015


Article type: Paper
DOI: 10.1039/C5OB00621J
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2015,13, 6225-6241
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    Synthesis and evaluation of cationic norbornanes as peptidomimetic antibacterial agents

    S. M. Hickey, T. D. Ashton, S. K. Khosa, R. N. Robson, J. M. White, J. Li, R. L. Nation, H. Y. Yu, A. G. Elliott, M. S. Butler, J. X. Huang, M. A. Cooper and F. M. Pfeffer, Org. Biomol. Chem., 2015, 13, 6225
    DOI: 10.1039/C5OB00621J

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