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Synthesis and evaluation of cationic norbornanes as peptidomimetic antibacterial agents

Version 2 2024-06-03, 07:10
Version 1 2015-08-18, 13:36
journal contribution
posted on 2024-06-03, 07:10 authored by SM Hickey, TD Ashton, SK Khosa, RN Robson, JM White, J Li, RL Nation, HY Yu, AG Elliott, MS Butler, JX Huang, MA Cooper, Fred PfefferFred Pfeffer
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.

History

Journal

Organic and biomolecular chemistry

Volume

13

Pagination

6225-6241

Location

Cambridge, Eng.

ISSN

1477-0539

Language

eng

Publication classification

C Journal article, C1 Refereed article in a scholarly journal

Copyright notice

2015, Royal Society of Chemistry

Issue

22

Publisher

Royal Society of Chemistry