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Molecules 2012, 17(8), 9129-9141; doi:10.3390/molecules17089129

Synthesis and Antibacterial Activities of Amphiphilic Neomycin B-based Bilipid Conjugates and Fluorinated Neomycin B-based Lipids

1,2, 1, 1, 3 and 1,3,*
Received: 17 July 2012 / Revised: 25 July 2012 / Accepted: 26 July 2012 / Published: 2 August 2012
(This article belongs to the Special Issue Advances in Medicinal Chemistry of Antibiotics)
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Investigating the effect of lipid hydrophobicity on the activity of amphiphilic neomycin B conjugates, six polycationic amphiphiles (PAs) were created. Four of the new compounds incorporated either palmitic or arachidic di-lipid lysine tails, while two had single fluorinated undecanoic acid tails. The basicity of half of the compounds was increased through the incorporation of six guanidine moieties, in order to assess the effect of base strength on antimicrobial activity. A panel of ten bacteria was used for the testing, with seven strains obtained from the American Type Culture Collection series and three clinical isolates from Canadian Intensive Care Units. When compared to previous results with hydrocarbon monolipids the PAs all compounds were found to have reduced activity, though the hemolytic activity of the compounds with fluorinated tails was sharply reduced, with only a moderate reduction in antimicrobial activity.
Keywords: aminoglycosides; cationic amphiphiles; carbohydrates; antibacterials aminoglycosides; cationic amphiphiles; carbohydrates; antibacterials
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Bera, S.; Dhondikubeer, R.; Findlay, B.; Zhanel, G.G.; Schweizer, F. Synthesis and Antibacterial Activities of Amphiphilic Neomycin B-based Bilipid Conjugates and Fluorinated Neomycin B-based Lipids. Molecules 2012, 17, 9129-9141.

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