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Methylimidazolium ionic liquids - A new class of forever chemicals with endocrine disrupting potential

Lookup NU author(s): Dr Tarek Abdelghany, Lanyu Fan, Ben Air, Dr Alistair Leitch, Dr Martin Cooke, Dr Agnieszka Bronowska, Professor Matthew Wright

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This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).


Abstract

© 2024 The Author(s)A class of chemical with a potentially important perceived future contribution to the net zero carbon goal (as “green” solvents) is the methylimidazolium ionic liquids (MILs). These solvents are used in industrial processes such as biofuel production yet little is known about their environmental stability or toxicity in man although one MIL – 1-octyl-3-methylimidazolium (M8OI) – has been shown to activate the human estrogen receptor alpha (ERα). The stabilities of the chloride unsubstituted methylimidazolium (MI) and MILs possessing increasing alkyl chain lengths (2C, 1-ethyl-3-methylimidazolium (EMI); 4C, 1-butyl-3-methylimidazolium (BMI); 6C; 1-hexyl-3-methylimidazolium (HMI), 8C, M8OI; 10C, 1-decyl-3-methylimidazolium (DMI)) were examined in river water and a human liver model system. The MILs were also screened for their abilities to activate the human ERα in vitro and induce uterine growth in pre-pubertal rats in vivo. Short chain MILs (EMI, BMI and HMI) underwent negligible metabolism and mineralisation in river water; were not metabolised in a model of human liver metabolism; activated the human ERα in vitro and were estrogenic in vivo in rats. A structure-based computational approach predicted short chain MIL binding to both the estrogen binding site and an additional site on the human estrogen receptor alpha. Longer chain MILs (M8OI and DMI) were metabolised in river water and partially mineralised. Based on structure-activity considerations, some of these environmentally-derived metabolites may however, remain a hazard to the population. MILs therefore have the potential to become forever chemicals with adverse effects to both man, other animals and the environment in general.


Publication metadata

Author(s): Abdelghany TM, Hedya S, Charlton A, Fan L, Fazili N, Air B, Leitch AC, Cooke M, Bronowska AK, Wright MC

Publication type: Article

Publication status: Published

Journal: Chemosphere

Year: 2024

Volume: 363

Print publication date: 01/09/2024

Online publication date: 15/07/2024

Acceptance date: 09/07/2024

Date deposited: 05/08/2024

ISSN (print): 0045-6535

ISSN (electronic): 1879-1298

Publisher: Elsevier Ltd

URL: https://doi.org/10.1016/j.chemosphere.2024.142827

DOI: 10.1016/j.chemosphere.2024.142827

Data Access Statement: Data will be made available on request.

PubMed id: 39019179


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Funding

Funder referenceFunder name
EP/S022791/1EPSRC
EPR51209X1
EPSRC

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