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The Synthesis, Self-Assembled Structures, and Microbicidal Activity of Cationic Gemini Surfactants with Branched Tridecyl Chains

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Department of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, SK-83232 Bratislava, Slovakia
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State Institute for Drug Control, SK-82508 Bratislava, Slovakia
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Faculty of Pharmacy, Comenius University, 83232 Bratislava, Slovakia
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Department of Physical Chemistry of Drugs, Faculty of Pharmacy, Comenius University, SK-83232 Bratislava, Slovakia
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Department of Cell and Molecular Biology of Drugs, Faculty of Pharmacy, Comenius University, SK-83232 Bratislava, Slovakia
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NMR Laboratory, Comenius University, SK-83232 Bratislava, Slovakia
*
Author to whom correspondence should be addressed.
Academic Editors: Bogumil E. Brycki and Łukasz Chrzanowski
Molecules 2019, 24(23), 4380; https://doi.org/10.3390/molecules24234380
Received: 24 September 2019 / Revised: 25 November 2019 / Accepted: 28 November 2019 / Published: 30 November 2019
(This article belongs to the Special Issue Microbiocides Chemistry)
Cationic gemini surfactants with polymethylene spacer and linear alkyl chains containing an even number of carbon atoms have been extensively studied in the recent past, with the emphasis put on the determination of their aggregation behaviour in aqueous solution and their biological properties. However, the information on the aggregation of branched gemini surfactants with an odd number of carbon atoms in their alkyl chains is only sparsely reported in the literature. To help cover this gap in the research of cationic gemini surfactants, a series of branched bisammonium cationic gemini surfactants with an odd number of carbon atoms in alkyl chains (tridecane-2-yl chains) and a polymethylene spacer with a variable length ranging from 3 to 12 carbon atoms have been synthesized and investigated. Critical micelle concentration, which was determined by three methods, was found to be in the order 10−4 mol/L. A comparison of the obtained data of the novel series of tridecyl chain geminis with those of gemini surfactants with dodecyl chains and an identical spacer structure revealed that structural differences between both series of gemini surfactants result in different aggregation and surface properties for surfactants with 6 and 8 methylene groups in the spacer (N,N’-bis(tridecane-2-yl)-N,N,N’,N’-tetramethylhexane-1,6-diaminium dibromide and N,N’-bis(tridecane-2-yl)-N,N,N’,N’-tetramethyloctane-1,8-diaminium dibromide) with the cmc values 8.2 × 10−4 mol/L and 6.5 × 10−4 mol/L, respectively, as determined by surface tension measurements. Particle size analysis showed the formation of small stable spherical micelles in the interval between 2.8 and 5 nm and with zeta potential around +50 mV, which are independent of surfactant concentration and increase with the increasing spacer length. Microbicidal activity of 13-s-13 gemini surfactants was found to be efficient against Gram-positive, Gram-negative bacteria and yeast. View Full-Text
Keywords: gemini surfactant; polymethylene spacer; tridecyl chain; zeta potential; microbicidal activity gemini surfactant; polymethylene spacer; tridecyl chain; zeta potential; microbicidal activity
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MDPI and ACS Style

Pisárčik, M.; Pupák, M.; Lukáč, M.; Devínsky, F.; Hubčík, L.; Bukovský, M.; Horváth, B. The Synthesis, Self-Assembled Structures, and Microbicidal Activity of Cationic Gemini Surfactants with Branched Tridecyl Chains. Molecules 2019, 24, 4380.

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