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Bioorg Med Chem Lett ; 26(15): 3770-3, 2016 08 01.
Article in English | MEDLINE | ID: mdl-27287371

ABSTRACT

Staphylococcus aureus, a Gram positive coccal bacterium is a major cause of nosocomial infection. We report the synthesis of new triphenylamine phosphonium ionic liquids which are able to self-assemble into multiwall nanoassemblies and to reveal a strong bactericidal activity (MIC=0.5mg/L) for Gram positive bacteria (including resistant strains) comparable to that of standard antibiotics. Time kill, metabolism and fluorescence confocal microscopy studies show a quasi-instantaneously penetration of the nanoassemblies inside the bacteria resulting of a rapid blocking (30min) of their proliferation. As confirmed by rezasurin reduction monitoring, these compounds strongly affect the bacterial metabolism and a Gram positive versus Gram negative selectivity is clearly observed. These fluorescent phosphonium ionic liquid might constitute a useful tool for both translocation studies and to tackle infectious diseases related to the field of implantology.


Subject(s)
Amines/pharmacology , Anti-Bacterial Agents/pharmacology , Fluorescent Dyes/pharmacology , Ionic Liquids/pharmacology , Organophosphorus Compounds/pharmacology , Amines/chemical synthesis , Amines/chemistry , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Bacteria/cytology , Bacteria/drug effects , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , Fluorescent Dyes/chemical synthesis , Fluorescent Dyes/chemistry , Ionic Liquids/chemical synthesis , Ionic Liquids/chemistry , Microbial Sensitivity Tests , Molecular Structure , Organophosphorus Compounds/chemical synthesis , Organophosphorus Compounds/chemistry , Structure-Activity Relationship
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