2015
DOI: 10.1021/acs.langmuir.5b03347
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Biscationic Tartaric Acid-Based Amphiphiles: Charge Location Impacts Antimicrobial Activity

Abstract: Cationic amphiphiles have received increasing attention as antimicrobials given their unique ability to disrupt bacteria cell membranes. While extensive research has demonstrated that amphiphiles' hydrophobic-to-charge ratio significantly modulates antibacterial activity, less work has focused on elucidating the specific impact of charge location on amphiphile bioactivity. In this study, two series of cationic amphiphiles, termed bola-like and gemini-like, were synthesized with analogous hydrophobic-to-charge … Show more

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Cited by 17 publications
(20 citation statements)
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“…All reagents and solvents were purchased from Sigma-Aldrich (Milwaukee, WI) and used as received unless otherwise mentioned. Di- tert -butyl L-tartrate 22 and di-2-bocaminoethyltartramide 23 were prepared as previously published. Anhydrous dimethylformamide (DMF) was dried over 4 Å molecular sieves at room temperature at least overnight prior to use.…”
Section: Methodsmentioning
confidence: 99%
“…All reagents and solvents were purchased from Sigma-Aldrich (Milwaukee, WI) and used as received unless otherwise mentioned. Di- tert -butyl L-tartrate 22 and di-2-bocaminoethyltartramide 23 were prepared as previously published. Anhydrous dimethylformamide (DMF) was dried over 4 Å molecular sieves at room temperature at least overnight prior to use.…”
Section: Methodsmentioning
confidence: 99%
“…To test such a possibility, we examined the interaction of cationic PU-1 and PU-2 capsules with two model lipid vesicles by isothermal calorimetry (ITC) studies (Figures and S7). The vesicles were constructed from commercially available lipids, such as DPPG + DPPE (88:12) or DPPC, which mimic the bacterial or mammalian cell membrane, respectively. In a typical ITC experiment, the lipid vesicle dispersion was injected into a given polymer solution (lipid/polymer 10:1).…”
Section: Resultsmentioning
confidence: 99%
“…The fluorescent probe 5(6)-carboxyfluorescein (CF), the detergent Triton X-100, and HEPES buffer were purchased from Sigma-Aldrich (St. Louis, MO). The CAms were synthesized as described previously in detail . Briefly, bola-like amphiphiles were synthesized by first reacting bromo-containing alkanoic acids of varying hydrophobic chain lengths with concentrated ammonium hydroxide to generate amine-terminated alkanoic acid intermediates.…”
Section: Methodsmentioning
confidence: 99%