TMEDA-derived biscationic amphiphiles: An economical preparation of potent antibacterial agents |
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| Affiliation: | 1. Department of Chemistry, Villanova University, Villanova, PA 19085, United States;2. Department of Chemistry, Temple University, Philadelphia, PA 19122, United States;1. School of Biosystems Engineering, Agriculture and Food Science Centre, University College Dublin, Belfield, Dublin 4, Ireland;2. School of Physics, University College Dublin, Belfield, Dublin, Ireland;3. School of Public Health, Physiotherapy & Population Science, University College Dublin, Belfield, Dublin 4, Ireland;1. Faculty of Science, Suez University, Suez, Egypt;2. Institut für Anorganische Chemie und Strukturchemie, Heinrich-Heine Universität Düsseldorf, 40204 Düsseldorf, Germany;1. A.E. Arbuzov Institute of Organic and Physical Chemistry of the Russian Academy of Sciences, Arbuzov Str. 8, Kazan 420088, Russian Federation;2. Kazan State University, Kazan 420008, 18 Kremlyovskaya str., Russian Federation |
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| Abstract: | Bis-alkylated derivatives of N,N,N′,N′-tetramethylethylenediamine (TMEDA) represent a well-known class of versatile biscationic amphiphiles, owing to their low cost and ease of preparation. Asymmetric TMEDA derivatives, however, have been studied significantly less, particularly in regards to their antimicrobial properties. We have thus prepared a series of 36 mono- and bis-alkylated TMEDA derivatives to evaluate their inhibition of bacterial growth. This series of compounds showed low micromolar activity against a panel of four bacteria. Optimal inhibition was observed when the biscationic amphiphiles possessed modest asymmetry and were composed of between 20 and 24 total carbon atoms in the side chains. These amphiphiles were prepared in a simple two-step procedure, utilizing inexpensive materials and atom-economical reactions, making them practical for further development. |
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| Keywords: | Amphiphile Antibacterial Antiseptic Asymmetric TMEDA |
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