4.6 Article

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

期刊

MOLECULES
卷 17, 期 8, 页码 9129-9141

出版社

MDPI AG
DOI: 10.3390/molecules17089129

关键词

aminoglycosides; cationic amphiphiles; carbohydrates; antibacterials

资金

  1. Natural Sciences and Engineering Research Council of Canada (NSERC)
  2. Canadian Institutes for Health Research (CIHR)
  3. Manitoba Health Research Council (MHRC)

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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.

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