The antimicrobial activity of mono-, bis-, tris-, and tetracationic amphiphiles derived from simple polyamine platforms |
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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. Department of Pharmaceutical Sciences, Manchester University College of Pharmacy, 10627 Diebold Rd, Fort Wayne, IN 46845, United States;2. Department of Microbiology and Immunology, Indiana University School of Medicine, 2101 Coliseum Blvd, Fort Wayne, IN 46805, United States;1. Faculty of Science, Suez University, Suez, Egypt;2. Institut für Anorganische Chemie und Strukturchemie, Heinrich-Heine Universität Düsseldorf, 40204 Düsseldorf, Germany;1. Division of Drug Discovery Research, Korea Research Institute of Chemical Technology, Yuseong-gu, Daejeon 305-343, Republic of Korea;2. Department of Medicinal and Pharmaceutical Chemistry, University of Science and Technology, Yuseong-gu, Daejeon 305-350, Republic of Korea;1. Laboratory of Synthetic Organic Chemistry, Department of Chemistry, University of Patras, GR-26504 Patras, Greece;2. Department of Biochemistry, School of Medicine, University of Patras, GR-26504 Patras, Greece;3. Department of Public Health, School of Medicine, University of Patras, GR-26504 Patras, Greece;1. School of Petroleum and Chemical Engineering, Dalian University of Technology, State Key Laboratory of Fine Chemicals, 2 Dagong Road, Liaodongwan New District, Panjin 124221, China;2. School of Food and Environment, Dalian University of Technology, 2 Dagong Road, Liaodongwan New District, Panjin 124221, China |
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| Abstract: | A series of 34 amphiphilic compounds varying in both number of quaternary ammonium groups and length of alkyl chains has been assembled. The synthetic preparations for these structures are simple and generally high-yielding, proceeding in 1–2 steps without the need for chromatography. Antibacterial MIC data for these compounds were determined, and over half boast single digit MIC values against a series of gram-positive and gram-negative bacteria. MIC variation mostly hinged on the length of the alkyl chain, where a dodecyl group led to optimal activity; surprisingly, the number of cations and/or basic nitrogens was less important in dictating bioactivity. Additional structural variation was prepared in a trisamine series dubbed 12,3,X,3,12, providing a series of potent amphiphiles functionalized with varied allyl, alkyl, and benzyl groups. Tetraamines were also investigated, culminating in a two-step preparation of a tetracationic structure that showed only modestly improved bioactivity versus amphiphiles with two or three cations. |
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| Keywords: | Amphiphile Antibacterial Biscationic Triscationic Tetracationic |
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