{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T16:59:01Z","timestamp":1790355541316,"version":"4.1.0"},"reference-count":35,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2025,3,12]],"date-time":"2025-03-12T00:00:00Z","timestamp":1741737600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"MCIN\/AEI\/10.13039\/501100011033","award":["PID2022-136354-NBI00"],"award-info":[{"award-number":["PID2022-136354-NBI00"]}]},{"name":"MCIN\/AEI\/10.13039\/501100011033","award":["PTA2020-018511-I"],"award-info":[{"award-number":["PTA2020-018511-I"]}]},{"name":"MCIN\/AEI\/10.13039\/501100011033","award":["PRE2022-000837"],"award-info":[{"award-number":["PRE2022-000837"]}]},{"name":"MCIN\/AEI\/10.13039\/501100011033","award":["PID2022-136354-NBI00"],"award-info":[{"award-number":["PID2022-136354-NBI00"]}]},{"name":"MCIN\/AEI\/10.13039\/501100011033","award":["PTA2020-018511-I"],"award-info":[{"award-number":["PTA2020-018511-I"]}]},{"name":"MCIN\/AEI\/10.13039\/501100011033","award":["PRE2022-000837"],"award-info":[{"award-number":["PRE2022-000837"]}]},{"name":"MCIN\/AEI\/10.13039\/501100011033","award":["PID2022-136354-NBI00"],"award-info":[{"award-number":["PID2022-136354-NBI00"]}]},{"name":"MCIN\/AEI\/10.13039\/501100011033","award":["PTA2020-018511-I"],"award-info":[{"award-number":["PTA2020-018511-I"]}]},{"name":"MCIN\/AEI\/10.13039\/501100011033","award":["PRE2022-000837"],"award-info":[{"award-number":["PRE2022-000837"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Choline-based ionic liquids (ILs) have gained attention as antimicrobial and antibiofilm agents due to their biocompatibility and tuneable antimicrobial properties. However, a significant drawback of amphiphilic choline-based ILs is their decreasing biodegradability as the alkyl chain length increases. To address this issue and enhance the ecotoxicological profile of these compounds, a labile ester functionality was incorporated into the alkyl side chain. This strategic modification aims to improve biodegradation rates while maintaining the desirable antimicrobial properties of the ILs. A series of ester-functionalized choline-based ionic liquids (CnECholBr) with alkyl chains containing from 10 to 14 carbon atoms were synthesized, and their self-aggregation behaviour in aqueous solutions was studied. Their antimicrobial properties were then tested against clinically significant bacteria and yeasts, as well as their effectiveness in eliminating MRSA and C. albicans biofilms. Furthermore, the ecotoxicological properties of these compounds were investigated by assessing their aerobic biodegradability and aquatic toxicity using luminescent bacteria. The results indicated that CnECholBr exhibit higher surface activity and biodegradation rates than non-functionalized choline-based ILs. Conversely, their antimicrobial and antibiofilm activity was found to be lower to that of non-functionalized choline-based ILs. Among the compounds evaluated, the C12ECholBr was identified as the most effective antimicrobial and antibiofilm agent.<\/jats:p>","DOI":"10.3390\/molecules30061280","type":"journal-article","created":{"date-parts":[[2025,3,13]],"date-time":"2025-03-13T04:18:32Z","timestamp":1741839512000},"page":"1280","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Self-Assembly, Antimicrobial Properties and Biodegradability of Ester-Functionalized Choline-Based Surface-Active Ionic Liquids"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9967-3472","authenticated-orcid":false,"given":"Mar\u00eda Teresa","family":"Garc\u00eda","sequence":"first","affiliation":[{"name":"Department of Surfactants and Nanobiotechnology, Institute for Advanced Chemistry of Catalonia (IQAC-CSIC), 08034 Barcelona, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elena","family":"Bautista","sequence":"additional","affiliation":[{"name":"Department of Surfactants and Nanobiotechnology, Institute for Advanced Chemistry of Catalonia (IQAC-CSIC), 08034 Barcelona, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3696-021X","authenticated-orcid":false,"given":"Lourdes","family":"P\u00e9rez","sequence":"additional","affiliation":[{"name":"Department of Surfactants and Nanobiotechnology, Institute for Advanced Chemistry of Catalonia (IQAC-CSIC), 08034 Barcelona, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0001-9445-0541","authenticated-orcid":false,"given":"Sergio","family":"V\u00e1zquez","sequence":"additional","affiliation":[{"name":"Department of Surfactants and Nanobiotechnology, Institute for Advanced Chemistry of Catalonia (IQAC-CSIC), 08034 Barcelona, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,3,12]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2857","DOI":"10.1080\/10408398.2015.1077192","article-title":"Antimicrobial resistance: A global emerging threat to public health systems","volume":"57","author":"Ferri","year":"2017","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"957","DOI":"10.1016\/j.watres.2012.11.027","article-title":"Urban wastewater treatment plants as hotspots for the release of antibiotics in the environment: A review","volume":"47","author":"Michael","year":"2013","journal-title":"Water Res."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1186\/s13756-020-00830-6","article-title":"Biofilm exacerbates antibiotic resistance: Is this a current oversight in antimicrobial stewardship?","volume":"9","author":"Bowler","year":"2020","journal-title":"Antimicrob. Resist. Infect. Control"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1016\/j.ijantimicag.2015.02.016","article-title":"The antimicrobial potential of ionic liquids: A source of chemical diversity for infection and biofilm control","volume":"46","author":"Pendleton","year":"2015","journal-title":"Int. J. Antimicrob. Agents"},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Gali\u00e9, S., Garc\u00eda-Guti\u00e9rrez, C., Migu\u00e9lez, E.M., Villar, C.J., and Lomb\u00f3, F. (2018). Biofilms in the Food Industry: Health Aspects and Control Methods. Front. Microbiol., 9.","DOI":"10.3389\/fmicb.2018.00898"},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Carrascosa, C., Raheem, D., Ramos, F., Saraiva, A., and Raposo, A. (2021). Microbial Biofilms in the Food Industry\u2014A Comprehensive Review. Int. J. Environ. Res. Public Health, 18.","DOI":"10.3390\/ijerph18042014"},{"key":"ref_7","unstructured":"European Centre for Disease Prevention and Control (2025, March 09). Last-Line Antibiotics Are Failing: Options to Address This Urgent Threat to Patients and Healthcare Systems. Available online: https:\/\/www.ecdc.europa.eu\/en\/publications-data\/last-line-antibiotics-are-failing-options-address-urgent-threat-patients-and."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"117077","DOI":"10.1016\/j.molliq.2021.117077","article-title":"Choline-based ionic liquids for planktonic and biofilm growth control of bacillus cereus and pseudomonas fluorescens","volume":"346","author":"Pereira","year":"2022","journal-title":"J. Mol. Liq."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"164","DOI":"10.1016\/j.jcis.2010.11.063","article-title":"Self-aggregation and antimicrobial activity of imidazolium and pyridinium based ionic liquids in aqueous solution","volume":"355","author":"Cornellas","year":"2011","journal-title":"J. Colloid Interface Sci."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"38","DOI":"10.1016\/j.aca.2020.05.072","article-title":"Efficacy of imidazolium and piperidinium based ionic liquids on inhibiting biofilm formation on titanium and carbon steel surfaces","volume":"1126","author":"Anandkumar","year":"2020","journal-title":"Anal. Chim. Acta"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"7132","DOI":"10.1021\/acs.chemrev.6b00562","article-title":"Biological Activity of Ionic Liquids and Their Application in Pharmaceutics and Medicine","volume":"117","author":"Egorova","year":"2017","journal-title":"Chem. Rev."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"4962","DOI":"10.1039\/b900201d","article-title":"On the concept of ionicity in ionic liquids","volume":"11","author":"MacFarlane","year":"2009","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"6633","DOI":"10.1021\/acs.chemrev.7b00246","article-title":"Introduction: Ionic Liquids","volume":"117","author":"Lei","year":"2017","journal-title":"Chem. Rev."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"166","DOI":"10.1039\/b315270g","article-title":"Biodegradable Ionic Liquids: Part I. Concept, Preliminary Targets and Evaluation","volume":"6","author":"Gathergood","year":"2004","journal-title":"Green Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"8200","DOI":"10.1039\/C5CS00444F","article-title":"Biodegradation of ionic liquids\u2014A critical review","volume":"44","author":"Jordan","year":"2015","journal-title":"Chem. Soc. Rev."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1595","DOI":"10.1039\/b913057h","article-title":"phosphonium ionic liquids: Design, synthesis and evaluation of biodegradability","volume":"11","author":"Atefi","year":"2009","journal-title":"Green Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"821","DOI":"10.1039\/b900787c","article-title":"Further investigation of the biodegradability of imidazolium ionic liquids","volume":"11","author":"Harjani","year":"2009","journal-title":"Green Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1573","DOI":"10.1002\/cbic.201700233","article-title":"Efflux Pumps Might Not Be the Major Drivers of QAC Resistance in Methicillin-Resistant Staphylococcus Aureus","volume":"18","author":"Jennings","year":"2017","journal-title":"ChemBioChem"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"3559","DOI":"10.1016\/j.tet.2016.01.014","article-title":"From antimicrobial activity to mechanism of resistance: The multifaceted role of simple quaternary ammonium compounds in bacterial eradication","volume":"72","author":"Minbiole","year":"2016","journal-title":"Tetrahedron"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"5909","DOI":"10.1002\/slct.201600864","article-title":"Choline-Based Ionic Liquids: Improvement of Antimicrobial Activity","volume":"1","author":"Siopa","year":"2016","journal-title":"ChemistrySelect"},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Garc\u00eda, M.T., Bautista, E., de la Fuente, A., and P\u00e9rez, L. (2023). Cholinium-Based Ionic Liquids as Promising Antimicrobial Agents in Pharmaceutical Applications: Surface Activity, Antibacterial Activity and Ecotoxicological Profile. Pharmaceutics, 15.","DOI":"10.3390\/pharmaceutics15071806"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"234","DOI":"10.1016\/j.molliq.2016.11.136","article-title":"Choline based ionic liquids and their applications in organic transformation","volume":"227","author":"Gadilohar","year":"2017","journal-title":"J. Mol. Liq."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"121366","DOI":"10.1016\/j.ijpharm.2021.121366","article-title":"Applications of choline-based ionic liquids in drug delivery","volume":"612","author":"Li","year":"2022","journal-title":"Int. J. Pharm."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"2536","DOI":"10.1021\/la304752e","article-title":"Aggregation Behavior and Antimicrobial Activity of Ester-Functionalized Imidazolium- and Pyridinium-Based Ionic Liquids in Aqueous Solution","volume":"29","author":"Garcia","year":"2013","journal-title":"Langmuir"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"318","DOI":"10.1016\/j.colsurfb.2014.09.033","article-title":"Self-assembly and antimicrobial activity of long-chain amide-functionalized ionic liquids in aqueous solution","volume":"123","author":"Garcia","year":"2014","journal-title":"Colloids Surf. B Biointerfaces"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"6511","DOI":"10.1021\/acs.langmuir.7b00505","article-title":"Micellization and Antimicrobial Properties of Surface-Active Ionic Liquids Containing Cleavable Carbonate Linkages","volume":"33","author":"Garcia","year":"2017","journal-title":"Langmuir"},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Rosen, M.J., and Kunjappu, J.T. (2012). Surfactants and Interfacial Phenomena, John Wiley & Sons. [4th ed.].","DOI":"10.1002\/9781118228920"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"28","DOI":"10.1016\/j.cocis.2019.11.009","article-title":"Structure\u2013activity relationship of cationic surfactants as antimicrobial agents","volume":"45","author":"Zhou","year":"2020","journal-title":"Curr. Opin. Colloid Interface Sci."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1401","DOI":"10.1002\/cmdc.201600176","article-title":"Building a Better Quaternary Ammonium Compound (QAC): Branched Tetracationic Antiseptic Amphiphiles","volume":"11","author":"Forman","year":"2016","journal-title":"ChemMedChem"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"9276","DOI":"10.1021\/la1001336","article-title":"Cationic Ester-Containing Gemini Surfactants: Physical\u2212Chemical Properties","volume":"26","author":"Holmberg","year":"2010","journal-title":"Langmuir"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1016\/j.jpha.2015.11.005","article-title":"Methods for in Vitro Evaluating Antimicrobial Activity: A Review","volume":"6","author":"Balouiri","year":"2016","journal-title":"J. Pharm. Anal."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2615","DOI":"10.1038\/s41596-021-00515-3","article-title":"Microtiter Plate Assays to Assess Antibiofilm Activity against Bacteria","volume":"16","author":"Haney","year":"2021","journal-title":"Nat. Protoc."},{"key":"ref_33","first-page":"525","article-title":"Validation of the red blood cell test system as in vitro assay for the rapid screening of irritation potential of surfactants","volume":"1","author":"Pape","year":"1987","journal-title":"Mol. Toxicol."},{"key":"ref_34","unstructured":"OECD (2014). OECD Test No. 310: Ready Biodegradability\u2014CO2 in Sealed Vessels (Headspace Test), OECD Publishing. OECD Guidelines for the Testing of Chemicals, Section 3."},{"key":"ref_35","unstructured":"(2009). Water Quality\u2014Determination of the Inhibitory Effect of Water Samples on the Light Emission of Vibrio fischeri (Luminescent Bacteria Test)\u2014Part 3: Method Using Freeze-Dried Bacteria (Standard No. UNE-EN ISO 11348-3-2009)."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/6\/1280\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T16:52:41Z","timestamp":1760028761000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/6\/1280"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,3,12]]},"references-count":35,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2025,3]]}},"alternative-id":["molecules30061280"],"URL":"https:\/\/doi.org\/10.3390\/molecules30061280","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,3,12]]}}}