Lysis of membrane lipids promoted by small organic molecules: Reactivity depends on structure but not lipophilicity.

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"

SUBMITTER: Britt HM 

PROVIDER: S-EPMC7176411 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature