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. 2019 Sep 25;9:13856. doi: 10.1038/s41598-019-49862-y

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© The Author(s) 2019

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

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Anchor design. Different anchor scaffold structures and proposed modes of anchoring (A) Anchor based on aza-crown ether scaffold has a 6-bond spacing over a rigid aromatic system giving the two lipophilic chains an approximate spacing of 0.7 nm and allowing each chain to interact with a different subset of lipids in the bilayer. (B) In the anchor based on 3-amino-1,2-propanediol scaffold both chains are attached to the same atom, favoring intramolecular interactions of the two chains, effectively resulting in a bigger lipophilic moiety which is expected to interact with the membrane in a concerted manner (C) Molecular representation of average lipid chain distances (red lines) for relaxed palmityl chains in aza crown ether and amino propanediol membrane anchors (hydrogens not shown for clarity) and top view of the aza crown ether macrocycle with hydrogen bonded (green dotted lines) ammonium head group of aminoethanol lipids from the lipid bilayer.