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

Molecules

Smritilekha Bera¹  Ramesh Dhondikubeer¹  Brandon Findlay¹  George G. Zhanel² 

[1] Department of Chemistry, University of Manitoba, Winnipeg, MB R3T 2N2, Canada;Department of Medical Microbiology, University of Manitoba, Winnipeg, MB R3E 3P4, Canada

关键词: aminoglycosides;    cationic amphiphiles;    carbohydrates;    antibacterials;   

DOI  :  10.3390/molecules17089129

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2012 by the authors; licensee MDPI, Basel, Switzerland.