Synthesis and Characterization of Surface-Active Ionic Liquids Used in the Disruption of Escherichia Coli Cells


Twelve surface-active ionic liquids (SAILs) and surface-active derivatives, based on imidazolium, ammonium, and phosphonium cations and containing one, or more, long alkyl chains in the cation and/or the anion, were synthetized and characterized. The aggregation behavior of these SAILs in water, as well as their adsorption at solution/air interface, were studied by assessing surface tension and conductivity. The CMC values obtained (0.03-6.0 mM) show a high propensity of these compounds to self-aggregate in aqueous media. Their thermal properties were also characterized, namely the melting point and decomposition temperature by using DSC and TGA, respectively. Furthermore, the toxicity of these SAILs was evaluated using the marine bacteria Aliivibrio fischeri (Gram-negative). According to the EC50 values obtained (0.3-2.7 mg L-1), the surface-active compounds tested should be considered toxic or highly toxic. Their ability to induce cell disruption of Escherichia coli cells (also Gram-negative), releasing the intracellular green fluorescent protein (GFP) produced, was investigated. The results clearly evidence the capability of these SAILs to act as cell disruption agents.



subject category

Chemistry; Physics


Sintra, TE; Vilas, M; Martins, M; Ventura, SPM; Ferreira, AIMCL; Santos, LMNBF; Goncalves, FJM; Tojo, E; Coutinho, JAP

our authors


This work was developed within the scope of the project CICECO-Aveiro Institute of Materials, FCT Ref. UID/CTM/50011/2019, financed by national funds through the FCT/MCTES. This work was supported by the Integrated Programme of SR&TD SusPhoto-Solutions - Solucoes Fotovoltaicas Sustentaveis (reference CENTRO-01-0145-FEDER-000005), co-funded by Centro 2020 program, Portugal 2020, European Union, through the European Regional Development Fund. The authors thank FCT for the financial support through the project FAPESP/19793/2014, for the doctoral grant SFRH/BD/122220/2016 of M. Martins and for the IF/00402/2015 contract of S.P.M. Ventura. Thanks are due to FundacAo para a Ciencia e Tecnologia (FCT), Lisbon, Portugal, European Social Fund (ESF) for the project CIQUP, University of Porto (Projects: PEst-UID/QUI/00081/2013, FCUP-CIQ-UP-NORTE-07-0124-FEDER-000065) and Project NORTE-01-0145-FEDER-000028, Sustainable Advanced Materials (SAM). A.I.M.C.L.F. thanks FCT for the Post-Doc: SFRH/BPD/84891/2012. Thanks are due for the financial support to CESAM (UID/AMB/50017 - POCI-01-0145- FEDER-007638), to FCT/MCTES through national funds (PIDDAC), and the co-funding by the FEDER, within the PT2020 Partnership Agreement and Compete 2020.

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