Wojcieszak Marta, Zięba Sylwia, Dubis Alina T, Karolak Maciej, Pałkowski Łukasz, Marcinkowska Agnieszka, Skrzypczak Andrzej, Putowska Alicja, Materna Katarzyna
Faculty of Chemical Technology, Poznan University of Technology, Berdychowo 4, 60-965 Poznań, Poland.
Department of Molecular Crystals, Institute of Molecular Physics Polish Academy of Sciences, Smoluchowskiego 17, 60-179 Poznań, Poland.
Molecules. 2024 Dec 5;29(23):5743. doi: 10.3390/molecules29235743.
This study investigates a series of surface-active ionic liquids (SAILs), including both imidazolium monocationic and dicationic compounds. These compounds are promising candidates, as they combine unique surface properties with antimicrobial activity, aligning with modern trends in chemistry. The research encompasses synthesis, thermal analysis, and topographical assessment, focusing on the impact of the amphiphilic cationic moiety, alkyl chain length, and the spatial relationship between the imidazolium ring and the phenyl substituent on the compounds' physicochemical behavior. An added value of this work lies in the integration of theoretical calculations related to their behavior in solution and at the air-water interface, revealing spontaneous adsorption (negative Gibbs free energy of adsorption values, ΔG). The results indicate that dicationic imidazolium SAILs have a greater tendency to form micelles but are less effective at reducing surface tension compared to their monocationic counterparts. Topography analyses of SAILs with 12 carbon atoms further highlight these differences. Notably, the dicationic SAIL with 12 carbon atoms in the spacer exhibited an impressive MIC of 0.007 mmol L against , consistent with findings showing that dicationic SAILs outperformed conventional antifungal agents, such as amphotericin B and fluconazole, at equivalent concentrations. Overall, the synthesized SAILs demonstrate superior surface activity compared to commercial surfactants and show potential as disinfectant agents.
本研究调查了一系列表面活性离子液体（SAILs），包括咪唑鎓单阳离子和双阳离子化合物。这些化合物是很有前景的候选物，因为它们将独特的表面性质与抗菌活性结合在一起，符合现代化学趋势。该研究涵盖了合成、热分析和形貌评估，重点关注两亲性阳离子部分、烷基链长度以及咪唑鎓环与苯基取代基之间的空间关系对化合物物理化学行为的影响。这项工作的一个附加值在于整合了与其在溶液和空气 - 水界面行为相关的理论计算，揭示了自发吸附（吸附值的负吉布斯自由能，ΔG）。结果表明，与单阳离子咪唑鎓SAILs相比，双阳离子咪唑鎓SAILs形成胶束的倾向更大，但在降低表面张力方面效果较差。对含有12个碳原子的SAILs的形貌分析进一步突出了这些差异。值得注意的是，间隔基中含有12个碳原子的双阳离子SAIL对[具体微生物未提及]的最低抑菌浓度（MIC）为0.007 mmol/L，这与表明双阳离子SAILs在等效浓度下优于传统抗真菌剂（如两性霉素B和氟康唑）的研究结果一致。总体而言，合成的SAILs与商业表面活性剂相比表现出卓越的表面活性，并显示出作为消毒剂的潜力。
