Small structural alterations greatly influence the membrane affinity of lipophilic ligands: Membrane interactions of bafilomycin A1 and its desmethyl derivative bearing 19F-labeling

[Display omitted] Molecular behavior under bilayer membrane environments is one of the important research topics concerning how organic molecules exert their biological activities when interacting with cellular membranes. However, chemistry-based approaches to this property have not been successful...

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Published inBioorganic & medicinal chemistry Vol. 27; no. 8; pp. 1677 - 1682
Main Authors Hayashi, Tatsuru, Tsuchikawa, Hiroshi, Umegawa, Yuichi, Murata, Michio
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 15.04.2019
Subjects
Bafilomycin
Lipophilic ligand
Membrane affinity
PAMPA
Solid-state NMR
Solid-state NMR
Bafilomycin
PAMPA
Membrane affinity
Lipophilic ligand
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Summary:[Display omitted] Molecular behavior under bilayer membrane environments is one of the important research topics concerning how organic molecules exert their biological activities when interacting with cellular membranes. However, chemistry-based approaches to this property have not been successful when compared with the structural biological strategy on ligand-receptor interactions. Here, we investigated the molecular behavior of the lipophilic ATPase inhibitor bafilomycin A1 and its derivatives under a lipid environment from a chemical point of view. Our results revealed significant differences in membrane affinity and dynamics among ligands having different inhibitory potencies, suggesting the specific contribution of ligand-membrane interactions to their biological activity.
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ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2019.03.017