TY - JOUR

T1 - Synthesis, biocompatibility, and antimicrobial properties of glucose-based ionic liquids

AU - Jopp, Stefan

AU - Fleischhammer, Tabea

AU - Lavrentieva, Antonina

AU - Kara, Selin

AU - Meyer, Johanna

N1 - Acknowledgements: SJ thanks the German Research Center (Deutsche Forschungsgemeinschaft, DFG) for the financial support (NFDI4-Cat; DFG grant no. 441926934). AL and TF thank the German Research Center (Deutsche Forschungsgemeinschaft, DFG) for the fnancial support (DFG grant no 398007461 488). SK and JM thank the Ministry for Science and Culture for Lower Saxony for the Holen & Halten starting grant (grant no. 12.5-76251-17-9/20). We also like to thank Martin Paehler, Martina Weiß, Caroline Mueller, Laura Schmitz from the Institute of Technical Chemistry TCI (Leibniz University Hannover), and Sandra Diederich from the Institute of Chemistry (University of Rostock) for their support on the day-to-day laboratory routine. Furthermore, we thank Sina Lambrecht from the Institute of Chemistry (University of Rostock), Tom Kunde and Riekje Biermann from the TCI (Leibniz University Hannover) for their assistance in the lab. Lastly, we thank Dr Carsten Kreyenschulte (Leibniz Institute for Catalysis, Rostock) and Dr Fanny Langschwager (Faculty of Mechanical Engineering and Marine Technologies, University of Rostock) for the measurements of SEM-EDX and ICP-OES, respectively.

PY - 2023/8/8

Y1 - 2023/8/8

N2 - The diversity in structure, the variety in chirality, as well as the large occurrence of carbohydrates in nature, led to the development of the next generation of ionic liquids (ILs). These carbohydrate-based ionic liquids, also known as CHILs, are expected to overcome limitations such as aquatic ecotoxicity and poor biodegradability. In this work, we present the glucosyl imidazolium ILs, obtained via a simple two to three-step synthesis with total yields up to 90%. These compounds were obtained with several variations in alkyl- and aromatic side chains, glycosidic groups, anions, and protecting groups to study the influence of these variations on the biocompatibility and antimicrobial properties of the CHILs. The in vitro studies confirmed the biocompatibility of most of the CHILs for L929 mouse fibroblasts at 10 −2 mol L −1, a feat not achieved by commercial imidazolium ILs. We could confirm observed trends, like increased cytotoxicity with increasing alkyl chain length, as well as higher fluorinated anions. Additionally, some of the here reported novel CHILs had significantly higher IC 50 values than comparable imidazolium, pyridinium, and pyrrolidinium-based ILs. Additionally, antibiotic resistance is an increasingly serious threat to global health. Consequently, the development of new substances with antibiotic properties is of high priority. The before-synthesized CHILs were investigated in their overall antimicrobial behavior towards a Gram-negative strain (Escherichia coli K-12), a Gram-positive strain (Bacillus subtilis), as well as a common yeast (Candida auris WT) via the disk diffusion test. The minimum inhibition concentration (MIC), minimum bactericidal concentration (MBC), and minimum fungicidal concentration (MFC) were determined from the active substances. Similar to the biocompatibility experiments, correlations can be found between the length of the alkyl chain, the non-polarity of the structure, as well as the amount of fluorine in the counterion. For Candida auris, GMIM-NTf 2 as well as GOIM-I show the strongest effect, with a MIC and MFC of 1 mmol L −1 and 5 mmol L −1, respectively.

AB - The diversity in structure, the variety in chirality, as well as the large occurrence of carbohydrates in nature, led to the development of the next generation of ionic liquids (ILs). These carbohydrate-based ionic liquids, also known as CHILs, are expected to overcome limitations such as aquatic ecotoxicity and poor biodegradability. In this work, we present the glucosyl imidazolium ILs, obtained via a simple two to three-step synthesis with total yields up to 90%. These compounds were obtained with several variations in alkyl- and aromatic side chains, glycosidic groups, anions, and protecting groups to study the influence of these variations on the biocompatibility and antimicrobial properties of the CHILs. The in vitro studies confirmed the biocompatibility of most of the CHILs for L929 mouse fibroblasts at 10 −2 mol L −1, a feat not achieved by commercial imidazolium ILs. We could confirm observed trends, like increased cytotoxicity with increasing alkyl chain length, as well as higher fluorinated anions. Additionally, some of the here reported novel CHILs had significantly higher IC 50 values than comparable imidazolium, pyridinium, and pyrrolidinium-based ILs. Additionally, antibiotic resistance is an increasingly serious threat to global health. Consequently, the development of new substances with antibiotic properties is of high priority. The before-synthesized CHILs were investigated in their overall antimicrobial behavior towards a Gram-negative strain (Escherichia coli K-12), a Gram-positive strain (Bacillus subtilis), as well as a common yeast (Candida auris WT) via the disk diffusion test. The minimum inhibition concentration (MIC), minimum bactericidal concentration (MBC), and minimum fungicidal concentration (MFC) were determined from the active substances. Similar to the biocompatibility experiments, correlations can be found between the length of the alkyl chain, the non-polarity of the structure, as well as the amount of fluorine in the counterion. For Candida auris, GMIM-NTf 2 as well as GOIM-I show the strongest effect, with a MIC and MFC of 1 mmol L −1 and 5 mmol L −1, respectively.

UR - http://www.scopus.com/inward/record.url?scp=85175159489&partnerID=8YFLogxK

U2 - 10.1039/d3su00191a

DO - 10.1039/d3su00191a

M3 - Article

VL - 1

SP - 1751

EP - 1764

JO - RSC Sustainability

JF - RSC Sustainability

IS - 7

ER -