Advertisement

Biophysical Reviews

, Volume 11, Issue 3, pp 395–398 | Cite as

Comparison of two different partially fluorinated phosphatidylcholines with the perfluorobutyl group on thermotropic properties of the bilayer membrane and reconstituted bacteriorhodopsin

  • Tamami Yanagi
  • Toshiyuki TakagiEmail author
  • Hiroshi TakahashiEmail author
  • Takashi Kikukawa
  • Hideki Amii
  • Masashi SonoyamaEmail author
Letter to the Editor

Introduction

Fluorinated surfactants (Shepherd and Holzenburg 1995; Popot 2010; Frotscher et al. 2015) and phospholipids (Santaella et al. 1991; Yoder et al. 2007; Takai et al. 2008; Gagnon et al. 2018) are now attracting more and more attention in biophysical fields because the incorporation of fluorine atoms provides distinctive physical properties to amphiphilic molecules, which would open up a new way of structural and functional characterization of membrane proteins (MPs). In particular, a novel partially fluorinated analog of dimyristoylphosphatidylcholine (DMPC), F4-DMPC (Fig.  1, m = 9; diF4H10-PC was used as the former abbreviation in the previous papers) (Yoshino et al. 2012; Takahashi et al. 2013; Okamoto et al. 2016), is of great promise for biophysical studies of MPs. Bacteriorhodopsin (bR) molecules in the F4-DMPC bilayer membrane form the native purple membrane (PM)–like two-dimensional crystals of trimers as the structural unit in the liquid-crystalline phase as well as...

Notes

Acknowledgments

We would like to thank Ms. Maria Takahashi for sample preparation and CD measurements of bR/F4-DPPC.

Funding information

This work was partly supported by Grants-in-Aid for Scientific Research (KAKENHI: 15K05558 to M.S., 18K06568 to T.T., 16K05509 to H.T., and 18H04381 to H.A.) from the Japan Society for the Promotion of Science (JSPS).

Compliance with ethical standards

Conflict of interest

Tamami Yanagi declares that she has no conflict of interest. Toshiyuki Takagi declares that he has no conflict of interest. Hiroshi Takahashi declares that he has no conflict of interest. Takashi Kikukawa declares that he has no conflict of interest. Hideki Amii declares that he has no conflict of interest. Masashi Sonoyama declares that he has no conflict of interest.

Ethical approval

This article does not contain any studies with human participants or animals performed by any of the authors.

References

  1. Cherry RJ, Muller U, Henderson R, Heyn MP (1978) Temperature-dependent aggregation of bacteriorhodopsin in dipalmitoyl- and dimyristoylphosphatidylcholine vesicles. J Mol Biol 121:283–298CrossRefGoogle Scholar
  2. Frotscher E, Danielczak B, Vargas C, Meister A, Durand G, Keller S (2015) A fluorinated detergent for membrane-protein applications. Angew Chem Int Ed 54:5069–5073CrossRefGoogle Scholar
  3. Gagnon MC, Auger M, Paquin JF (2018) Progress in the synthesis of fluorinated phosphatidylcholines for biological applications. Org Biomol Chem 16:4925–4941CrossRefGoogle Scholar
  4. Henderson R (1975) The structure of the purple membrane from Halobacterium halobium: analysis of the X-ray diffraction pattern. J Mol Biol 93:123–128CrossRefGoogle Scholar
  5. Heyn MP, Cherry RJ, Dencher NA (1981) Lipid-protein interactions in bacteriorhodopsin-dimyristoylphosphatidylcholine vesicles. Biochemistry 20:840–849CrossRefGoogle Scholar
  6. Krafft MP, Riess JG (2009) Chemistry, physical chemistry, and uses of molecular fluorocarbon-hydrocarbon diblocks, triblocks, and related compounds-unique “apolar” components for self-assembled colloid and interface engineering. Chem Rev 109:1714–1792CrossRefGoogle Scholar
  7. Okamoto Y, Motegi T, Morita K, Takagi T, Amii H, Kanamori T, Sonoyama M, Tero R (2016) Lateral diffusion and molecular interaction in a bilayer membrane consisting of partially fluorinated phospholipids. Langmuir 32:10712–10718CrossRefGoogle Scholar
  8. Popot JL (2010) Amphipols, nanodiscs, and fluorinated surfactants: three nonconventional approaches to studying membrane proteins in aqueous solutions. Annu Rev Biochem 79:737–775CrossRefGoogle Scholar
  9. Santaella C, Vierling P, Riess JG (1991) Highly stable liposomes derived from perfluoroalkylated glycerophosphocholines. Angew Chem Int Ed 30:567–568CrossRefGoogle Scholar
  10. Shepherd FH, Holzenburg A (1995) The potential of fluorinated surfactants in membrane biochemistry. Anal Biochem 224:21–27CrossRefGoogle Scholar
  11. Sonoyama M, Kikukawa T, Yokoyama Y, Demura M, Kamo N, Mitaku S (2009) Effect of molecular assembly on photocycle of reconstituted bacteriorhodopsin: significant blue shift of the late M photointermediate in the liquid crystalline phase. Chem Lett 38:1134–1135CrossRefGoogle Scholar
  12. Takahashi H, Yoshino M, Takagi T, Amii H, Baba T, Kanamori T, Sonoyama M (2013) Non-ideal mixing of dimyristoylphosphatidylcholine with its partially fluorinated analogue in hydrated bilayers. Chem Phys Lett 559:107–111CrossRefGoogle Scholar
  13. Takahashi H, Yoshino M, Morita K, Takagi T, Yokoyama Y, Kikukawa T, Amii H, Kanamori T, Sonoyama M (2019) Stability of the two-dimensional lattice of bacteriorhodopsin reconstituted in partially fluorinated phosphatidylcholine bilayers. Biochim Biophys Acta Biomembr 1861:631–642CrossRefGoogle Scholar
  14. Takai K, Takagi T, Baba T, Kanamori T (2008) Synthesis and monolayer properties of double-chained phosphatidylcholines containing perfluoroalkyl groups of different length. J Fluor Chem 129:686–690CrossRefGoogle Scholar
  15. Yoder NC, Kalsani V, Schuy S, Vogel R, Janshoff A, Kumar K (2007) Nanoscale patterning in mixed fluorocarbon-hydrocarbon phospholipid bilayers. J Am Chem Soc 129:9037–9043CrossRefGoogle Scholar
  16. Yokoyama Y, Negishi L, Kitoh T, Sonoyama M, Asami Y, Mitaku S (2010) Effect of lipid phase transition on molecular assembly and structural stability of bacteriorhodopsin reconstituted into phosphatidylcholine liposomes with different acyl-chain lengths. J Phys Chem B 114:15706–15711CrossRefGoogle Scholar
  17. Yoshino M, Takahashi H, Takagi T, Baba T, Morita K, Amii H, Kanamori T, Sonoyama M (2012) Effect of partial fluorination in the myristoyl groups on thermal and interfacial properties of dimyristoylphosphatidylcholine. Chem Lett 41:1495–1497CrossRefGoogle Scholar
  18. Yoshino M, Kikukawa T, Takahashi H, Takagi T, Yokoyama Y, Amii H, Baba T, Kanamori T, Sonoyama M (2013) Physicochemical studies of bacteriorhodopsin reconstituted in partially fluorinated phosphatidylcholine bilayers. J Phys Chem B 117:5422–5429CrossRefGoogle Scholar

Copyright information

© International Union for Pure and Applied Biophysics (IUPAB) and Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Division of Molecular Science, Faculty of Science and TechnologyGunma UniversityKiryuJapan
  2. 2.Biotechnology Research Institute for Drug DiscoveryNational Institute of Advanced Industrial Science and Technology (AIST)TsukubaJapan
  3. 3.Division of Pure and Applied Science, Graduate School of Science and TechnologyGunma UniversityMaebashiJapan
  4. 4.Faculty of Advanced Life ScienceHokkaido UniversitySapporoJapan
  5. 5.Global Station for Soft Matter, GI-CoREHokkaido UniversitySapporoJapan
  6. 6.Gunma University Center for Food Science and Wellness (GUCFW)Gunma UniversityMaebashiJapan
  7. 7.Gunma University Initiative for Advanced Research (GIAR)Gunma UniversityMaebashiJapan

Personalised recommendations