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Contrasting Effects of a Rigid Core and an Alkyl Chain in nCB on the Phase Behavior of Lipid Bilayers

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Department of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
*E-mail [email protected]; Ph +81 29 853 4239; Fax +81 29 853 6503 (K.S.).
Cite this: Langmuir 2016, 32, 23, 5966–5972
Publication Date (Web):May 24, 2016
https://doi.org/10.1021/acs.langmuir.6b00774
Copyright © 2016 American Chemical Society
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Abstract

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Molecules incorporated into biomembranes often bear both a core and an alkyl chain in a single molecule (e.g., sterols). To clarify the effects of these two parts of a molecule, the phase behavior of a 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) bilayer containing 4-n-alkyl-4′-cyanobiphenyl (nCB) (n = 0–8) was investigated. The trends of the main transition temperature (Tm) with respect to n and of the pretransition temperature (Tp) with respect to nCB content changed at n = 3. It was therefore suggested that the two parts of the molecule had opposing effects on the phase behavior of DPPC bilayers. The core appears to perturb molecular ordering in the gel phase and lowers Tm (like cholesterol), while alkyl chains appear to order the lipids in the gel phase and raise Tm (like n-alkanes). In addition, Tm exhibits the so-called odd–even effect based on the alkyl chain length of the minor component, nCB. Depending on the value of n, the variation in Tp was dependent on the additive content, although the pretransition was rarely observed at high contents.

Cited By


This article is cited by 7 publications.

  1. Mafumi Hishida, Naofumi Shimokawa, Yuki Okubo, Shun Taguchi, Yasuhisa Yamamura, Kazuya Saito. Phase Transition from the Interdigitated to Bilayer Membrane of a Cationic Surfactant Induced by Addition of Hydrophobic Molecules. Langmuir 2020, 36 (48) , 14699-14709. https://doi.org/10.1021/acs.langmuir.0c02609
  2. Atsushi Kashiro, Wakana Kohno, Takayuki Ishida. Odd–Even Effect on the Spin-Crossover Temperature in Iron(II) Complex Series Involving an Alkylated or Acyloxylated Tripodal Ligand. Inorganic Chemistry 2020, 59 (14) , 10163-10171. https://doi.org/10.1021/acs.inorgchem.0c01296
  3. Satoshi Nakata, Yuta Yamaguchi, Koichi Fukuhara, Mafumi Hishida, Hiroyuki Kitahata, Yukiteru Katsumoto, Yuki Umino, Mitsuhiro Denda, Noriyuki Kumazawa. Characteristic responses of a 1,2-dioleoyl-sn-glycero-3-phosphocholine molecular layer to monovalent and divalent metal cations. Colloids and Surfaces A: Physicochemical and Engineering Aspects 2020, 602 , 125115. https://doi.org/10.1016/j.colsurfa.2020.125115
  4. Hatsuho Usuda, Mafumi Hishida, Elizabeth G. Kelley, Yasuhisa Yamamura, Michihiro Nagao, Kazuya Saito. Interleaflet coupling of n -alkane incorporated bilayers. Physical Chemistry Chemical Physics 2020, 22 (10) , 5418-5426. https://doi.org/10.1039/C9CP06059F
  5. Mafumi Hishida, Ryuta Yanagisawa, Yasuhisa Yamamura, Kazuya Saito. Phase separation of a ternary lipid vesicle including n -alkane: Rugged vesicle and bilayer flakes formed by separation between highly rigid and flexible domains. The Journal of Chemical Physics 2019, 150 (6) , 064904. https://doi.org/10.1063/1.5080177
  6. Hatsuho Usuda, Mafumi Hishida, Yasuhisa Yamamura, Kazuya Saito. Common Effects of Incorporated n -Alkane Derivatives on Molecular Packing and Phase Behavior of DPPC Bilayers. Chemistry Letters 2018, 47 (12) , 1512-1514. https://doi.org/10.1246/cl.180747
  7. Hitoshi Matsuki, Kentaro Kato, Hirotsugu Okamoto, Shuntaro Yoshida, Masaki Goto, Nobutake Tamai, Shoji Kaneshina. Ligand partitioning into lipid bilayer membranes under high pressure: Implication of variation in phase-transition temperatures. Chemistry and Physics of Lipids 2017, 209 , 9-18. https://doi.org/10.1016/j.chemphyslip.2017.10.002

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