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Cyclopentane rings in hydrophobic chains of a phospholipid enhance the bilayer stability to electric breakdown

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Abstract

Archaeal lipids ensure unprecedented stability of archaea membranes in extreme environments. Here, we incorporate a characteristic structural feature of an archaeal lipid, the cyclopentane ring, into hydrocarbon chains of a short-chain (C12) phosphatidylcholine to explore whether the insertion would allow such a lipid (1,2-di-(3-(3-hexylcyclopentyl)-propanoate)-sn-glycero-3-phosphatidylcholine, diC12cp-PC) to form stable bilayers at room temperature. According to fluorescence-based assays, in water diC12cp-PC formed liquid-crystalline bilayers at room temperature. Liposomes produced from diC12cp-PC retained calcein for over a week when stored at +4 °C. diC12cp-PC could also form model bilayer lipid membranes that were by an order of magnitude more stable to electrical breakdown than egg PC membranes. Molecular dynamics simulation showed that the cyclopentane fragment fixes five carbon atoms (or four C–C bonds), which is compensated by the higher mobility of the rest of the chain. This was found to be the reason for the remarkable stability of the diC12cp-PC bilayer: restricted conformational mobility of a chain segment increases the membrane bending modulus (compared to a normal hydrocarbon chain of the same length). Here, higher stiffness practically does not affect the line tension of a membrane pore edge. Rather it makes it more difficult for diC12cp-PC to rearrange in order to line the edge of a hydrophilic pore; therefore, fewer pores are formed.

Graphical abstract: Cyclopentane rings in hydrophobic chains of a phospholipid enhance the bilayer stability to electric breakdown

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Supplementary files

Article information


Submitted
07 Oct 2019
Accepted
02 Mar 2020
First published
03 Mar 2020

Soft Matter, 2020, Advance Article
Article type
Paper

Cyclopentane rings in hydrophobic chains of a phospholipid enhance the bilayer stability to electric breakdown

O. V. Batishchev, A. S. Alekseeva, D. S. Tretiakova, T. R. Galimzyanov, A. Yu. Chernyadyev, N. R. Onishchenko, P. E. Volynsky and I. A. Boldyrev, Soft Matter, 2020, Advance Article , DOI: 10.1039/C9SM02001B

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