Synthesis and evaluation of cationic norbornanes as peptidomimetic antibacterial agents

Hickey, Shane M., Ashton, Trent D., Khosa, Simren K., Robson, Ryan N., White, Jonathan M., Li, Jian, Nation, Roger L., Yu, Heidi Y., Elliott, Alysha G., Butler, Mark S., Huang, Johnny X., Cooper, Matthew A. and Pfeffer, Frederick M. 2015, Synthesis and evaluation of cationic norbornanes as peptidomimetic antibacterial agents, Organic and biomolecular chemistry, vol. 13, no. 22, pp. 6225-6241, doi: 10.1039/c5ob00621j.

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Title Synthesis and evaluation of cationic norbornanes as peptidomimetic antibacterial agents
Author(s) Hickey, Shane M.
Ashton, Trent D.ORCID iD for Ashton, Trent D.
Khosa, Simren K.
Robson, Ryan N.
White, Jonathan M.
Li, Jian
Nation, Roger L.
Yu, Heidi Y.
Elliott, Alysha G.
Butler, Mark S.
Huang, Johnny X.
Cooper, Matthew A.
Pfeffer, Frederick M.ORCID iD for Pfeffer, Frederick M.
Journal name Organic and biomolecular chemistry
Volume number 13
Issue number 22
Start page 6225
End page 6241
Total pages 17
Publisher Royal Society of Chemistry
Place of publication Cambridge, Eng.
Publication date 2015-06-14
ISSN 1477-0539
Keyword(s) Anti-Bacterial Agents
Dose-Response Relationship, Drug
Gram-Negative Bacteria
Gram-Positive Bacteria
Microbial Sensitivity Tests
Structure-Activity Relationship
Summary 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.
Language eng
DOI 10.1039/c5ob00621j
Field of Research 0304 Medicinal And Biomolecular Chemistry
0305 Organic Chemistry
1115 Pharmacology And Pharmaceutical Sciences
030503 Organic Chemical Synthesis
030401 Biologically Active Molecules
030302 Nanochemistry and Supramolecular Chemistry
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1 Refereed article in a scholarly journal
Copyright notice ©2015, Royal Society of Chemistry
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