Lysis of membrane lipids promoted by small organic molecules : reactivity depends on structure but not lipophilicity
Britt, Hannah M. and Prakash, Aruna S. and Appleby, Sanna and Mosely, Jackie A. and Sanderson, John M. (2020) Lysis of membrane lipids promoted by small organic molecules : reactivity depends on structure but not lipophilicity. Science Advances, 6 (17). aaz8598. ISSN 2375-2548 (https://doi.org/10.1126/sciadv.aaz8598)
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Abstract
Several organic molecules of low molecular weight (<150 Da) are demonstrated to have substantial membrane-lytic potential despite having a low predicted lipophilicity (logD < 1 at neutral pH). In aqueous liposome dispersions, 38 aromatic compounds were tested for their ability to either promote lipid hydrolysis or directly participate in chemical reactions with lipid molecules. Behaviors observed included acyl transfer from the lipid to form a lipidated compound, both with and without concomitant lysolipid formation; increases in the rate of lipid hydrolysis without lipidation; and no reactivity. The variation in activity, including a notably higher activity for heterocycles such as amino-substituted benzimidazoles and indazoles, demonstrates the potential to predict or “design-in” lytic activity once the rules that govern reactivity are better understood. The nature of this chemical instability has significant ramifications for the use or presence of lipids in diverse fields such as materials chemistry, food chemistry, and cell physiology.
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Item type: Article ID code: 72477 Dates: DateEvent22 April 2020Published30 January 2020AcceptedSubjects: Science > Chemistry
Medicine > Pharmacy and materia medicaDepartment: Faculty of Science > Strathclyde Institute of Pharmacy and Biomedical Sciences Depositing user: Pure Administrator Date deposited: 27 May 2020 11:41 Last modified: 07 Aug 2024 01:48 Related URLs: URI: https://strathprints.strath.ac.uk/id/eprint/72477