TY - JOUR
T1 - Ionic Liquids as Biocompatible Antibacterial Agents
T2 - A Case Study on Structure-Related Bioactivity on Escherichia coli
AU - Fernandes, Margarida M.
AU - Carvalho, Estela O.
AU - Correia, Daniela M.
AU - Esperança, José M. S. S.
AU - Padrão, Jorge
AU - Ivanova, Kristina
AU - Hoyo, Javier
AU - Tzanov, Tzanko
AU - Lanceros-Mendez, Senentxu
N1 - Funding Information:
info:eu-repo/grantAgreement/FCT/POR_NORTE/SFRH%2FBPD%2F121464%2F2016/PT#
info:eu-repo/grantAgreement/FCT/POR_NORTE/SFRH%2FBPD%2F121526%2F2016/PT#
info:eu-repo/grantAgreement/FCT/POR_NORTE/SFRH%2FBD%2F145455%2F2019/PT#
info:eu-repo/grantAgreement/FCT/9471 - RIDTI/PTDC%2FBTM-MAT%2F28237%2F2017/PT#
info:eu-repo/grantAgreement/FCT/9471 - RIDTI/PTDC%2FEMD-EMD%2F28159%2F2017/PT#
info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50006%2F2020/PT#
info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50006%2F2020/PT#
The strategic funding UID/FIS/04650/2021 and UID/BIO/04469/2021. They acknowledge funding by the Spanish State Research Agency (AEI) and the European Regional Development Fund (ERFD) through the project PID2019-106099RB-C43/AEI/10.13039/501100011033 and from the Basque Government Industry Departments under the ELKARTEK program.
Publisher Copyright:
© 2022 American Chemical Society.
PY - 2022/10/19
Y1 - 2022/10/19
N2 - The potential of ionic liquids (ILs) to be used as antimicrobial agents for biomedical applications has been hindered by the fact that most of them are cytotoxic toward mammalian cells. Understanding the mechanism of bacterial and mammalian cellular damage of ILs is key to their safety design. In this work, we evaluate the antimicrobial activity and mode of action of several ILs with varying anions and cations toward the clinically relevant Gram-negative Escherichia coli. Langmuir monolayer technique was used to evaluate if the IL's mode of action was related to the bacterial cell membrane interaction for an effective E. coli killing. 1-Decyl-3-methylimidazolium bis(trifluoromethylsulfonyl) imide [DMIM][TFSI] and trihexyltetradecyl phosphonium bis(trifluoromethylsulfonyl) imide [P6,6,6,14][TFSI] were surface-active and induced bacterial cell lysis, through a membrane-disruption phenomenon on bacteria, in a mechanism that was clearly related to the long alkyl chains of the cation. 1-Ethyl-3-methylimidazolium hydrogen sulfate [EMIM][HSO4] was highly antimicrobial toward E. coli and found suitable for biological applications since it was harmless to mammalian cells at most of the tested concentrations. The results suggest that the imidazolium cation of the ILs is mostly responsible not only for their antimicrobial activity but also for their cytotoxicity, and the inclusion of different anions may tailor the ILs' biocompatibility without losing the capacity to kill bacteria, as is the case of [EMIM][HSO4]. Importantly, this IL was found to be highly antimicrobial even when incorporated in a polymeric matrix.
AB - The potential of ionic liquids (ILs) to be used as antimicrobial agents for biomedical applications has been hindered by the fact that most of them are cytotoxic toward mammalian cells. Understanding the mechanism of bacterial and mammalian cellular damage of ILs is key to their safety design. In this work, we evaluate the antimicrobial activity and mode of action of several ILs with varying anions and cations toward the clinically relevant Gram-negative Escherichia coli. Langmuir monolayer technique was used to evaluate if the IL's mode of action was related to the bacterial cell membrane interaction for an effective E. coli killing. 1-Decyl-3-methylimidazolium bis(trifluoromethylsulfonyl) imide [DMIM][TFSI] and trihexyltetradecyl phosphonium bis(trifluoromethylsulfonyl) imide [P6,6,6,14][TFSI] were surface-active and induced bacterial cell lysis, through a membrane-disruption phenomenon on bacteria, in a mechanism that was clearly related to the long alkyl chains of the cation. 1-Ethyl-3-methylimidazolium hydrogen sulfate [EMIM][HSO4] was highly antimicrobial toward E. coli and found suitable for biological applications since it was harmless to mammalian cells at most of the tested concentrations. The results suggest that the imidazolium cation of the ILs is mostly responsible not only for their antimicrobial activity but also for their cytotoxicity, and the inclusion of different anions may tailor the ILs' biocompatibility without losing the capacity to kill bacteria, as is the case of [EMIM][HSO4]. Importantly, this IL was found to be highly antimicrobial even when incorporated in a polymeric matrix.
KW - antimicrobial
KW - biocompatible
KW - Escherichia coli
KW - ionic liquids
KW - surface activity
UR - http://www.scopus.com/inward/record.url?scp=85141027808&partnerID=8YFLogxK
U2 - 10.1021/acsabm.2c00615
DO - 10.1021/acsabm.2c00615
M3 - Article
C2 - 36260814
AN - SCOPUS:85141027808
SN - 2576-6422
VL - 5
SP - 5181
EP - 5189
JO - ACS Applied Bio Materials
JF - ACS Applied Bio Materials
IS - 11
ER -