Effects of cationic head group structure on cytotoxicity and mitochondrial actions of amphiphilic ionic liquids.

Roy, R; York, E; Pacchini, E; Rawling, T

Effects of cationic head group structure on cytotoxicity and mitochondrial actions of amphiphilic ionic liquids.

Roy, R York, E Pacchini, E Rawling, T

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Publisher:: PERGAMON-ELSEVIER SCIENCE LTD
Publication Type:: Journal Article
Citation:: Food Chem Toxicol, 2024, 183, pp. 114202-114202
Issue Date:: 2024-01

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Field	Value	Language
dc.contributor.author	Roy, R
dc.contributor.author	York, E
dc.contributor.author	Pacchini, E
dc.contributor.author	Rawling, T https://orcid.org/0000-0002-6624-6586
dc.date.accessioned	2024-12-12T01:10:05Z
dc.date.available	2023-11-17
dc.date.available	2024-12-12T01:10:05Z
dc.date.issued	2024-01
dc.identifier.citation	Food Chem Toxicol, 2024, 183, pp. 114202-114202
dc.identifier.issn	0278-6915
dc.identifier.issn	1873-6351
dc.identifier.uri	http://hdl.handle.net/10453/182487
dc.description.abstract	Ionic liquids (ILs) are a class of low melting point salts with physicochemical properties that make them suitable for a range of industrial applications. Accumulating evidence suggests that certain ILs are cytotoxic and potential environmental pollutants, thus understanding the structural features that promote IL cytotoxicity is important. Amphiphilic ionic liquids (AmILs), a class of ILs with lipophilic N-alkyl chains, containing aromatic head groups are generally more cytotoxic than their aliphatic counterparts, however the impact of other head group properties are less clear. This study therefore sought to provide new structure activity relationship (SAR) insights regarding the role of the cationic head group on AmIL cytotoxicity. A series of AmILs bearing a range of structurally diverse aromatic cations varying in size, charge, and lipophilicity was synthesised and screened against human MDA-MB-231 breast cancer cells. It was found that larger and more lipophilic head groups increased cytotoxicity, although the magnitude of the changes were modest. The mitochondrial effects of representative ILs were assessed. The AmILs induced mitochondrial dysfunction in MDA-MB-231 cells at cytotoxic concentrations, suggesting that they target mitochondria. The new SAR information from this study may assist in the design of AmILs with controlled cytotoxicity.
dc.format	Print-Electronic
dc.language	eng
dc.publisher	PERGAMON-ELSEVIER SCIENCE LTD
dc.relation.ispartof	Food Chem Toxicol
dc.relation.isbasedon	10.1016/j.fct.2023.114202
dc.rights	info:eu-repo/semantics/openAccess
dc.subject	0908 Food Sciences
dc.subject.classification	Food Science
dc.subject.classification	3006 Food sciences
dc.subject.classification	3214 Pharmacology and pharmaceutical sciences
dc.subject.mesh	Cations
dc.subject.mesh	Group Structure
dc.subject.mesh	Humans
dc.subject.mesh	Ionic Liquids
dc.subject.mesh	Structure-Activity Relationship
dc.subject.mesh	Humans
dc.subject.mesh	Ionic Liquids
dc.subject.mesh	Group Structure
dc.subject.mesh	Structure-Activity Relationship
dc.subject.mesh	Cations
dc.subject.mesh	Humans
dc.subject.mesh	Cations
dc.subject.mesh	Group Structure
dc.subject.mesh	Structure-Activity Relationship
dc.subject.mesh	Ionic Liquids
dc.subject.mesh	Humans
dc.subject.mesh	Ionic Liquids
dc.subject.mesh	Group Structure
dc.subject.mesh	Structure-Activity Relationship
dc.subject.mesh	Cations
dc.title	Effects of cationic head group structure on cytotoxicity and mitochondrial actions of amphiphilic ionic liquids.
dc.type	Journal Article
utslib.citation.volume	183
utslib.location.activity	England
utslib.for	0908 Food Sciences
pubs.organisational-group	University of Technology Sydney
pubs.organisational-group	University of Technology Sydney/Faculty of Science
pubs.organisational-group	University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
utslib.copyright.status	open_access	*
pubs.consider-herdc	false
dc.date.updated	2024-12-12T01:10:04Z
pubs.publication-status	Published
pubs.volume	183

Abstract:

Ionic liquids (ILs) are a class of low melting point salts with physicochemical properties that make them suitable for a range of industrial applications. Accumulating evidence suggests that certain ILs are cytotoxic and potential environmental pollutants, thus understanding the structural features that promote IL cytotoxicity is important. Amphiphilic ionic liquids (AmILs), a class of ILs with lipophilic N-alkyl chains, containing aromatic head groups are generally more cytotoxic than their aliphatic counterparts, however the impact of other head group properties are less clear. This study therefore sought to provide new structure activity relationship (SAR) insights regarding the role of the cationic head group on AmIL cytotoxicity. A series of AmILs bearing a range of structurally diverse aromatic cations varying in size, charge, and lipophilicity was synthesised and screened against human MDA-MB-231 breast cancer cells. It was found that larger and more lipophilic head groups increased cytotoxicity, although the magnitude of the changes were modest. The mitochondrial effects of representative ILs were assessed. The AmILs induced mitochondrial dysfunction in MDA-MB-231 cells at cytotoxic concentrations, suggesting that they target mitochondria. The new SAR information from this study may assist in the design of AmILs with controlled cytotoxicity.

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http://hdl.handle.net/10453/182487