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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). eaaz8598.

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.

Item Type:Article
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Available under License - Creative Commons Attribution.
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Status:Peer-reviewed
Publisher Web site:https://doi.org/10.1126/sciadv.aaz8598
Publisher statement:This is an open-access article distributed under the terms of the Creative Commons Attribution license, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Date accepted:30 January 2020
Date deposited:05 May 2020
Date of first online publication:22 April 2020
Date first made open access:05 May 2020

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