Evaluation of antimicrobial properties of monocationic and dicationic surface-active ionic liquids

被引:16
作者
Wojcieszak, Marta [1 ]
Lewandowska, Aneta [1 ]
Marcinkowska, Agnieszka [1 ]
Palkowski, Lukasz [2 ]
Karolak, Maciej [2 ]
Skrzypczak, Andrzej [1 ]
Syguda, Anna [1 ]
Materna, Katarzyna [1 ]
机构
[1] Poznan Univ Tech, Dept Chem Technol, Ul Berdychowo 4, PL-60965 Poznan, Poland
[2] Nicolaus Copernicus Univ, Fac Pharm, Dept Pharmaceut Technol, Jurasza 2, PL-85089 Bydgoszcz, Poland
关键词
Antimicrobial activity; Micellization; Cell membrane; Surface-active ionic liquids; AGGREGATION BEHAVIOR; MICELLE FORMATION; ADSORPTION; MICELLIZATION;
D O I
10.1016/j.molliq.2023.121300
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
In the present study, a series of monocationic and dicationic surface-active ionic liquids (SAILs) were synthesized and characterized. The structures of SAILs were confirmed by spectral analyses of 1H NMR and 13C NMR. Additionally, the thermal properties of the synthesized monocationic and dicationic SAILs were determined using thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). Nevertheless, the crucial part of this work is to confirm the strong relationship between the structure, surface activity, and biological action of newly SAILs on bacteria (both G(-) and G(+)) and fungi. The elongation of the alkyl chain or linker in the imidazolium cation results in a decrease in the minimum inhibitory concentration (MIC). Dicationic SAILs containing more than eight carbon atoms in the linker showed antimicrobial activity. In contrast, a cutoff effect was observed for their monocationic analog. (c) 2023 Elsevier B.V. All rights reserved.
引用
收藏
页数:8
相关论文
共 57 条
[1]   Synthesis and Self-Assembly Properties of New Surface-Active 1-Alkylimidazolium Ionic Liquids in Aqueous Media [J].
Adam, Claudia G. ;
Fortunato, Graciela G. .
JOURNAL OF SURFACTANTS AND DETERGENTS, 2019, 22 (03) :501-513
[2]   Structure and properties of high stability geminal dicationic ionic liquids [J].
Anderson, JL ;
Ding, RF ;
Ellern, A ;
Armstrong, DW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (02) :593-604
[3]  
[Anonymous], 2002, J AM CHEM SOC, V124, DOI [10.1021/ja025281k, DOI 10.1021/JA025281K]
[4]   Cut-off effects in biological activities of surfactants [J].
Balgavy, P ;
Devinsky, F .
ADVANCES IN COLLOID AND INTERFACE SCIENCE, 1996, 66 :23-63
[5]   Interfacial and micellar properties of imidazolium-based monocationic and dicationic ionic liquids [J].
Baltazar, Quinner Q. ;
Chandawalla, Janaki ;
Sawyer, Keahna ;
Anderson, Jared L. .
COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS, 2007, 302 (1-3) :150-156
[6]   Ionic liquids as alternatives of surfactants in enhanced oil recovery-A state-of-the-art review [J].
Bera, Achinta ;
Belhaj, Hadi .
JOURNAL OF MOLECULAR LIQUIDS, 2016, 224 :177-188
[7]   Nanosegregation and Structuring in the Bulk and at the Surface of Ionic-Liquid Mixtures [J].
Bruce, Duncan W. ;
Cabry, Christopher P. ;
Lopes, Jose N. Canongia ;
Costen, Matthew L. ;
D'Andrea, Lucia ;
Grillo, Isabelle ;
Marshall, Brooks C. ;
McKendrick, Kenneth G. ;
Minton, Timothy K. ;
Purcell, Simon M. ;
Rogers, Sarah ;
Slattery, John M. ;
Shimizu, Karma ;
Smoll, Eric ;
Tesa-Serrate, Maria A. .
JOURNAL OF PHYSICAL CHEMISTRY B, 2017, 121 (24) :6002-6020
[8]   Surface-active ionic liquids: A review [J].
Buettner, Cornelia S. ;
Cognigni, Alice ;
Schroeder, Christian ;
Bica-Schroeder, Katharina .
JOURNAL OF MOLECULAR LIQUIDS, 2022, 347
[9]   Synthesis and antimicrobial properties of polymerizable quaternary ammoniums [J].
Caillier, Laurent ;
de Givenchy, Elisabeth Taffin ;
Levy, Richard ;
Vandenberghe, Yves ;
Geribaldi, Serge ;
Guittard, Frederic .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (08) :3201-3208
[10]   Recent progress in the assembly behavior of imidazolium-based ionic liquid surfactants [J].
Cao, Huijiao ;
Hu, Yimin ;
Xu, Wenlin ;
Wang, Yaqiong ;
Guo, Xia .
JOURNAL OF MOLECULAR LIQUIDS, 2020, 319