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Biosafety-inspired structural optimization of triazolium ionic liquids based on structure-toxicity relationships
Xiujiao Pan1, Lingzhi Li2, Hsin-Heng Huang3
1Institute of Environmental Research at Greater Bay Area, Key Laboratory for Water Quality and Conservation of the Pearl River Delta, Ministry of Education, Guangzhou University, Guangzhou 510006, China.
Journal of Hazardous Materials
|November 4, 2021
Summary
Ionic liquids (ILs) show varying toxicity based on cell type. Cation structure, particularly sidechain length and nitrogen content, significantly impacts IL cytotoxicity, guiding the design of safer alternatives.
Area of Science:
- Green Chemistry
- Toxicology
- Materials Science
Background:
- Ionic liquids (ILs) are replacing toxic organic solvents due to low vapor pressure and good solvency.
- ILs pose risks to aquatic environments, soils, and human health, necessitating toxicity reduction.
- Oral exposure is a primary route for human contact with ILs.
Purpose of the Study:
- To explore the cytotoxicity and molecular mechanisms of ionic liquids using a human cell panel.
- To identify structural features of ILs that influence toxicity, particularly for oral exposure.
- To provide guidelines for designing safer, 'green' ionic liquids.
Main Methods:
- Utilized a panel of human cell lines (stomach, intestinal, liver, kidney) to model oral exposure.
- Employed experimental and computational approaches to assess cytotoxicity and molecular mechanisms.
- Investigated the role of IL cation structure (sidechain length, nitrogen atoms) and anions in toxicity.
Main Results:
- Ionic liquid cytotoxicity is human cell line-dependent (FHC > GES-1 > HepG2 > HEK293), invalidating single-cell assays.
- IL cations, not anions, are the primary drivers of cytotoxicity.
- Longer hydrophobic sidechains on cations increase membrane perturbation, cell cycle arrest, and apoptosis; reducing sidechain length and increasing nitrogen atoms (triazolium vs. imidazolium) alleviates toxicity.
Conclusions:
- The cation's structural features are critical for modulating ionic liquid toxicity.
- Designing ILs with shorter sidechains and more nitrogen atoms in the cation core can reduce cytotoxicity.
- These findings offer a framework for developing next-generation, safer ionic liquids.
