title: Micellar and biochemical properties of (hemi)fluorinated surfactants are controlled by the size of the polar head.
abstract: Surfactants with fluorinated and hemifluorinated alkyl chains have yielded encouraging results in terms of membrane protein stability; however, the molecules used hitherto have either been chemically heterogeneous or formed heterogeneous micelles. A new series of surfactants whose polar head size is modulated by the presence of one, two, or three glucose moieties has been synthesized. Analytical ultracentrifugation and small-angle neutron scattering show that fluorinated surfactants whose polar head bears a single glucosyl group form very large cylindrical micelles, whereas those with two or three glucose moieties form small, homogeneous, globular micelles. We studied the homogeneity and stability of the complexes formed between membrane proteins and these surfactants by using bacteriorhodopsin and cytochrome b(6)f as models. Homogeneous complexes were obtained only with surfactants that form homogeneous micelles. Surfactants bearing one or two glucose moieties were found to be stabilizing, whereas those with three moieties were destabilizing. Fluorinated and hemifluorinated surfactants with a two-glucose polar head thus appear to be very promising molecules for biochemical applications and structural studies. They were successfully used for cell-free synthesis of the ion channel MscL.
authors.affiliation: Centre National de la Recherche Scientifique, Institut de Biologie Physico-Chimique, Unite Mixte de Recherche 7099, Paris, France. Cecile.Breyton@ibpc.fr
authors.forename: Cécile
authors.initials: C
authors.lastname: Breyton
authors.forename: Frank
authors.initials: F
authors.lastname: Gabel
authors.forename: Maher
authors.initials: M
authors.lastname: Abla
authors.forename: Yves
authors.initials: Y
authors.lastname: Pierre
authors.forename: Florence
authors.initials: F
authors.lastname: Lebaupain
authors.forename: Grégory
authors.initials: G
authors.lastname: Durand
authors.forename: Jean-Luc
authors.initials: JL
authors.lastname: Popot
authors.forename: Christine
authors.initials: C
authors.lastname: Ebel
authors.forename: Bernard
authors.initials: B
authors.lastname: Pucci
mesh_terms: D001665:Binding Sites; D003102:Colloids / Q000737:chemistry*; D017611:Fluorine Compounds / Q000737:chemistry*; D008565:Membrane Proteins / Q000737:chemistry* / Q000648:ultrastructure*; D008823:Micelles; D008968:Molecular Conformation; D010316:Particle Size; D011485:Protein Binding; D055672:Static Electricity; D013501:Surface-Active Agents / Q000737:chemistry*
chemical_list: D003102:Colloids; D017611:Fluorine Compounds; D008565:Membrane Proteins; D008823:Micelles; D013501:Surface-Active Agents
references.citation: J Biol Chem. 2001 Aug 31;276(35):32403-6
references.pmid: 11432878
references.citation: Science. 1997 Sep 12;277(5332):1676-81
references.pmid: 9287223
references.citation: Xenobiotica. 1994 Jun;24(6):535-41
references.pmid: 7975719
references.citation: Biochemistry. 2006 Feb 28;45(8):2629-35
references.pmid: 16489756
references.citation: Biochimie. 1998 May-Jun;80(5-6):515-30
references.pmid: 9782390
references.citation: FEBS Lett. 1978 Dec 15;96(2):322-6
references.pmid: 32075
references.citation: Org Lett. 1999 Dec 2;1(11):1689-92
references.pmid: 10905858
references.citation: J Struct Biol. 2001 Nov;136(2):144-57
references.pmid: 11886216
references.citation: J Biol Chem. 1995 Dec 8;270(49):29342-9
references.pmid: 7493968
references.citation: Bioorg Med Chem Lett. 2006 Nov 15;16(22):5827-31
references.pmid: 16962774
references.citation: Biochim Biophys Acta. 1977 Oct 17;470(2):185-201
references.pmid: 911827
references.citation: Biochem J. 2007 Apr 1;403(1):183-7
references.pmid: 17176254
references.citation: J Biol Chem. 1989 Mar 25;264(9):4907-15
references.pmid: 2522447
references.citation: J Biol Chem. 1997 Aug 29;272(35):21892-900
references.pmid: 9268322
references.citation: FEBS Lett. 2004 Apr 30;564(3):312-8
references.pmid: 15111115
references.citation: Biophys J. 2000 Mar;78(3):1606-19
references.pmid: 10692345
references.citation: Biochim Biophys Acta. 2000 Nov 23;1508(1-2):86-111
references.pmid: 11090820
references.citation: Langmuir. 2006 Oct 10;22(21):8881-90
references.pmid: 17014131
references.citation: Biophys J. 2008 May 1;94(9):3523-37
references.pmid: 18192360
references.citation: Biomater Artif Cells Immobilization Biotechnol. 1993;21(5):597-608
references.pmid: 8117849
references.citation: Nature. 2003 Nov 27;426(6965):413-8
references.pmid: 14647374
references.citation: Biophys J. 2008 Jun;94(11):4348-57
references.pmid: 18310255
references.citation: J Org Chem. 2008 Nov 7;73(21):8142-53
references.pmid: 18823145
references.citation: J Biol Chem. 1997 Aug 29;272(35):21901-8
references.pmid: 9268323