synthesis and antibacterial activities of amphiphilic neomycin b-based bilipid conjugates and fluorinated neomycin b-based lipids合成及抗菌活性的两亲性新霉素b-based生物脂轭合物和氟化新霉素b-based脂质.pdfVIP

Molecules 2012, 17, 9129-9141; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis and Antibacterial Activities of Amphiphilic Neomycin B-based Bilipid Conjugates and Fluorinated Neomycin B-based Lipids Smritilekha Bera 1,2, Ramesh Dhondikubeer 1, Brandon Findlay 1, George G. Zhanel 3 and Frank Schweizer 1,3,* 1 Department of Chemistry, University of Manitoba, Winnipeg, MB R3T 2N2, Canada 2 School of Chemical Sciences, Central University of Gujarat, Gandhinagar, Gujarat 382-030, India 3 Department of Medical Microbiology, University of Manitoba, Winnipeg, MB R3E 3P4, Canada * Author to whom correspondence should be addressed; E-Mail: schweize@cc.umanitoba.ca; Tel.: +1-204-474-7012; Fax: +1-204-474-7608. Received: 17 July 2012; in revised form: 25 July 2012 / Accepted: 26 July 2012 / Published: 2 August 2012 Abstract: 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