Mitochondrial Actions and Structure Activity Relationships of Cytotoxic Ionic Liquids

Duman, Meryem-Nur

Mitochondrial Actions and Structure Activity Relationships of Cytotoxic Ionic Liquids

Duman, Meryem-Nur

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Publication Type:: Thesis
Issue Date:: 2023

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Field	Value	Language
dc.contributor.author	Duman, Meryem-Nur
dc.date.accessioned	2024-06-20T01:02:13Z
dc.date.available	2024-06-20T01:02:13Z
dc.date.issued	2023
dc.identifier.uri	http://hdl.handle.net/10453/179584
dc.description	University of Technology Sydney. Faculty of Science.	en_US.UTF-8
dc.description.abstract	Ionic liquids (ILs) are a group of low melting point ionic compounds with physicochemical properties that can be tailored to suit wide variety of applications. While once touted as environmentally friendly and safe solvents, it is now clear that ILs are toxic towards a variety of organisms. As their popularity increases it is critical to understand the mechanisms by which ILs induce toxicity and to develop structure-activity relationship (SAR) that can guide the design of safe ILs. This thesis addresses these challenges. The first section of this thesis reports a mechanistic study based on the central hypothesis that aromatic ILs can accumulate in mitochondria by interacting with the mitochondrial membrane potential. It is shown that aromatic long chain ILs induce mitochondrial dysfunction consistent with targeting of the inner mitochondrial membrane, while aliphatic and short chain ILs failed to produce these effects. In the second section a structure activity relations ship study was conducted to determine the effect of IL headgroup substitution cytotoxicity. Substituent lipophilicity and electronic properties had minimal effect on cytotoxicity, while the capacity of the substituent to act as a hydrogen bond donor lowered IL cytotoxicity. These insights may assist in the design of safer ILs.	en_US.UTF-8
dc.format	Thesis (PhD)
dc.language.iso	en_US	en_US.UTF-8
dc.relation	https://opus.lib.uts.edu.au/bitstream/10453/179584/1/thesis.pdf
dc.rights	info:eu-repo/semantics/openAccess
dc.rights	The author owns the copyright in this thesis including all reproduction and reuse rights for the work. The work may not be altered without the permission of the copyright owner. Attribution is essential when quoting or paraphrasing from this thesis.
dc.rights	© 2023 Meryem-Nur Duman
dc.rights	au.edu.uts.lib/cph
dc.title	Mitochondrial Actions and Structure Activity Relationships of Cytotoxic Ionic Liquids	en_US.UTF-8
dc.type	Thesis
utslib.copyright.status	open_access	*

Abstract:

Ionic liquids (ILs) are a group of low melting point ionic compounds with physicochemical properties that can be tailored to suit wide variety of applications. While once touted as environmentally friendly and safe solvents, it is now clear that ILs are toxic towards a variety of organisms. As their popularity increases it is critical to understand the mechanisms by which ILs induce toxicity and to develop structure-activity relationship (SAR) that can guide the design of safe ILs. This thesis addresses these challenges. The first section of this thesis reports a mechanistic study based on the central hypothesis that aromatic ILs can accumulate in mitochondria by interacting with the mitochondrial membrane potential. It is shown that aromatic long chain ILs induce mitochondrial dysfunction consistent with targeting of the inner mitochondrial membrane, while aliphatic and short chain ILs failed to produce these effects. In the second section a structure activity relations ship study was conducted to determine the effect of IL headgroup substitution cytotoxicity. Substituent lipophilicity and electronic properties had minimal effect on cytotoxicity, while the capacity of the substituent to act as a hydrogen bond donor lowered IL cytotoxicity. These insights may assist in the design of safer ILs.

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http://hdl.handle.net/10453/179584