Relationship between molecular structure and supramolecular morphology of DODA-EO2-biotin and related lipids

Chemistry and Physics of Lipids

Volumn 89, Issue 1, 1997, Pages 15-30

  Huetz, Philippe ^a   Van Neuren, Stephanie ^a   Ringler, Philippe ^b   Kremer, Felix ^a   Van Breemen, Jan F L ^a   Wagenaar, Anno ^a   Engberts, Jan B F N ^a   Fraaije, Johannes G E M ^a   Brisson, Alain ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b INSTITUT DE GÉNÉTIQUE ET DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

Author keywords

Biotinylated lipids; Helical crystallization of proteins; Lipid tubules; Liposomes; Supramolecular aggregates

Indexed keywords

AMIDE; BIOTIN; LIPID; STREPTAVIDIN;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CHIRALITY; CRYSTALLIZATION; HYDRATION; MOLECULAR RECOGNITION; PRIORITY JOURNAL; SYNTHESIS; TRANSMISSION ELECTRON MICROSCOPY;

EID: 0030722129     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-3084(97)00055-8     Document Type: Article

References (61)

1. Ahlers, M., 1990. PhD dissertation. Mainz University, Germany.
2. Archibald, D.D., Mann, S., 1993a. Template mineralization of self-assembled anisotropic lipid microstructures. Nature 364, 430-433.
3. Archibald, D.D., Mann, S., 1993b. Structural studies of lipid fibers formed by sphingosine. Biochim. Biophys. Acta 1166, 154-162.
4. Archibald, D.D., Yager, P., 1992. Microstructural polymorphism in bovine brain galactocerebroside and its two major subfractions. Biochemistry 31, 9045-9055.
5. Arnold, M., Ringler, P., Brisson, A., 1995. A quantitative electrophoretic migration shift assay for analyzing the specific binding of proteins to lipid ligands in vesicles or micelles. Biochim. Biophys. Acta 1233, 198-204.
6. Bayer, E., Wilchek, M., 1974. Insolubilized biotin for the purification of avidin. Methods Enzymol. 34, 265-267.
7. Birault, V., Pozzi, G., Plobeck, N., Eifler, S., Schmutz, M., Palanche, T., Raya, J., Brisson, A., Nakatani, Y., Ourisson, G., 1996. Di(polyprenyl) phosphates as models for primitive membrane constituants: synthesis and phase properties. Chem. Eur. J. 2, 789-799.
8. Blankenburg, R., 1989. PhD Dissertation. Mainz University, Germany.
9. Burke, T.G., Rudolph, A.S., Price, R.R., Sheridan, J.P., Dalziel, A.W., Singh, A., Schoen, P.E., 1988. Differential scanning calorimetric study of the thermotropic phase behavior of a polymerizable, tubule-forming lipid. Chem. Phys. Lipids 48, 215-230.
10. Chapman, D., Owens, N.F., Walker, D.A., 1966. Physical studies of phospholipids. II. Monolayer studies of some synthetic 2,3-diacyl-DL-phosphatidylethanolamines and phosphatidylcholines containing trans double bonds. Biochim. Biophys. Acta 120, 148-155.
11. Chappell, J.S., Yager, P., 1991. Electrolyte effects on bilayer tubule formation by a diacetylenic phospholipid. Biophys. J. 60, 952-965.
12. DeTitta, G.T., Edmonds, J.W., Stallings, W., Donohue, J., 1976. Molecular structure of biotin. Results of two independent crystal structure investigations. J. Am. Chem. Soc. 98, 1920-1926.
13. Doig, A.J., Williams, D.H., 1992. Binding energy of an amide-amide hydrogen bond in aqueous and nonpolar solvents. J. Am. Chem. Soc. 114, 338-343.
14. Dubochet, J., Groom, M., Müller-Neuteboom, S., 1982. Advances in Optical and Electron Microscopy. In: Cosslett, V.E., Barer, R. (Eds.), Academic Press, London, pp. 107-135.
15. Ebato, H., Herron, J.N., Müller, W., Okahata, Y., Ringsdorf, H., Suci, P., 1992. Docking of a second functional protein layer to a streptavidin matrix on a solid support: studies with a quartz crystal microbalance. Angew. Chemie 31, 1087-1090.
16. Erdelen, C., 1993. PhD Dissertation. Mainz University, Germany.
17. Frankel, D.A., O'Brien, D.F., 1994. Supramolecular assemblies of diacetylenic aldonamides. J. Am. Chem. Soc. 116, 10057-10069.
18. Fromherz, P., Röcker, C., Rüppel, D., 1986. From discoid micelles to spherical vesicles - the concept of edge activity. Faraday Discuss. Chem. Soc. 81, 39-48.
19. Fuhrhop, J.-H., Köning, J., 1994. Membranes and Molecular Assemblies: The Synkinetic Approach, In: Stoddart, F.F., (Ed.), Cambridge University Press, Cambridge, pp. 99-148.
20. Fuhrhop, J.-H., Schnieder, P., Boekema, E., Helfrich, W., 1988. Lipid bilayer fibers from diastereomeric and enantiomeric N-octylaldonamides. J. Am. Chem. Soc. 110, 2861-2867.
21. Fuhrhop, J.-H., Schnieder, P., Rosenberg, J., Boekema, E., 1987. The chiral bilayer effect stabilizes micellar fibers. J. Am. Chem. Soc. 109, 3387-3390.
22. Georger, J.H., Singh, A., Price, R.R., Schnur, J.M., Yager, P., Schoen, P.E., 1987. Helical and tubular microstructures formed by polymerizable phosphatidylcholines. J. Am. Chem. Soc. 109, 6169-6175.
23. Giulieri, F., Guillod, F., Greiner, J., Krafft, M.-P., Riess, J.G., 1996. Anionic glucophospholipids - A new family of tubule-forming amphiphiles. Chem. Eur. J. 2, 1335-1339.
24. Giulieri, F., Krafft, M.-P., 1996. Self-organization of single-chain fluorinated amphiphiles with fluorinated alcohols. Thin Solid Films 284-285, 195-199.
25. Giulieri, F., Krafft, M.-P., Riess, J.G., 1994. Stable flexible fibers and rigid tubules made from single-chain perfluoroalkylated amphiphiles. Angew. Chem. Int. Ed. Engl. 33, 1514-1515.
26. Green, N.M., 1975. Avidin. Adv. Protein Chem. 29, 85-133.
27. Helfrich, W., 1986. Helical bilayer structures due to spontaneous torsion of the edges. J. Chem. Phys. 85, 1085-1087.
28. Helfrich, W., Prost, J., 1988. Intrinsic bending force in anisotropic membranes made of chiral molecules. Phys. Rev. A38, 3065-3068.
29. Hendrickson, W.A., Pähler, A., Smith, J.L., Satow, Y., Merritt, E.A., Phizackerley, R.P., 1989. Crystal structure of core streptavidin determined from multiwavelength anomalous diffraction of synchrotron radiation. Proc. Natl. Acad. Sci. USA 86, 2190-2194.
30. Imae, T., Takahashi, Y., Muramatsu, H., 1992. Formation of fibrous molecular assemblies by amino acid surfactants in water. J. Am. Chem. Soc. 114, 3414-3419.
31. Kaplun, A., Talmon, Y., Konikoff, F.M., Rubin, M., Eitan, A., Tadmor, M., Lichtenberg, D., 1994. Direct visualization of lipid aggregates in native human bile by light- and cryo-transmission electron-microscopy. FEBS Lett. 340, 78-82.
32. Köning, J., Boettcher, C., Winkler, H., Zeitler, E., Talmon, Y., Fuhrhop, J.-H., 1993. Magic angle (54.7°) gradient and minimal surfaces in quadruple micellar helices. J. Am. Chem. Soc. 115, 693-700.
33. Kulkarni, V.S., Anderson, W.H., Brown, R.E., 1995. Bilayer nanotubes and helical ribbons formed by hydrated galactosylceramides: acyl chain and headgroup effects. Biophys. J. 69, 1976-1986.
34. Kunitake, T., Okahata, Y., Shimomura, M., Yasunami, S., Takarabe, K., 1981. Formation of stable bilayer assemblies in water from single-chain amphiphiles. Relationship between the amphiphile structure and the aggregate morphology. J. Am. Chem. Soc. 103, 5401-5413.
35. Lasic, D.D., 1990. On the thermodynamic stability of liposomes. J. Coll. Interface Sci. 140, 302-304.
36. Lasic, D.D., 1993. Liposomes, From Physics to Applications. In: Lasic, D.D. (Ed.), Elsevier, Amsterdam.
37. Lubensky, T.C., Prost, J., 1992. Orientational order and vesicle shape. J. Phys. II 2, 371-382.
38. McCormick, D.B., Roth, J.A., 1970. Colorimetric determination of biotin and analogs. Methods Enzymol. 18A, 383-385.
39. 3) induced a ripple phase in supported unilamellar phospholipid bilayers. Biochemistry 33, 4439-4443.
40. Müller, W., 1993. PhD Dissertation. Mainz University, Germany.
41. Nakashima, N., Asakuma, S., Kim, J.-M., Kunitake, T., 1984. Helical superstructures are formed from chiral ammonium bilayers. Chem. Lett. 1709-1712
42. Nakashima, N., Asakuma, S., Kunitake, T., 1985. Optical microscopic study of helical superstructures of chiral bilayer membranes. J. Am. Chem. Soc. 107, 509-510.
43. Papahadjopoulos, D., Vail, W.J., Jacobson, K., Poste, G., 1975. Cochleate lipid cylinders: formation by fusion of unilamellar lipid vesicles. Biochim. Biophys. Acta 394, 483-491.
44. Pfannemüller, B., Welte, W., 1985. Amphiphilic properties of synthetic glycolipids based on amide linkages. I. Electron microscopic studies on aqueous gels. Chem. Phys. Lipids 37, 227-240.
45. Rand, R.P., Chapman, D., Larsson, K., 1975. Tilted hydrocarbon chains of dipalmitoyl lecithin become perpendicular to the bilayer before melting. Biophys. J. 15, 1117-1124.
46. Ratna, B.R., Baral-Tosh, S., Kahn, B., Schnur, J.M., Rudolph, A. S., 1992. Effect of alcohol chain length on tubule formation in 1,2-bis(10,12-tricosadiynoyl)-sn-glycero-3-phosphocholine. Chem. Phys. Lipids 63, 47-53.
47. Ringler, P., Müller, W., Ringsdorf, H., Brisson, A., 1997. Functionalized lipid tubules as tools for helical crystallization of proteins. Chem. Eur. J. 3, 620-625.
48. Schnur, J.M., 1993. Lipid tubules: a paradigm for molecularly engineered structures. Science 262, 1669-1676.
49. Selinger, J.V., MacKintosh, F.C., Schnur, J.M., 1996. Theory of cylindrical tubules and helical ribbons of chiral lipid membranes. Phys. Rev. E 53, 3804-3818.
50. Singh, A., Burke, T.G., Calvert, J.M., Georger, J.H., Herendeen, V., Price, R.R., Schoen, P.E., Yager, P., 1988. Lateral phase separation based on chirality in a polymerizable lipid and its influence on formation of tubular microstructures. Chem. Phys. Lipids 47, 135-148.
51. 13C NMR study of molecular conformations and disorder of N-octylhexonamides in microcrystals and supramolecular assemblies. J. Am. Chem. Soc. 116, 11969-11975.
52. Thomas, B.N., Safinya, C.R., Plano, R.J., Clark, N.A., 1995. Lipid tubule self-assembly: length dependence on cooling rate through a first-order phase transition. Science 267, 1635-1638.
53. Thomas, B.N., Safinya, C.R., Plano, R.J., Clark, N.A., Ratna, B.R., Shashidar, R., 1992. X-ray diffraction studies of tubules formed from a diacetylenic phosphocholine lipid. Mat. Res. Soc. Symp. Proc. 248, 83-88.
54. Traub, W., 1958. Possible biochemical implications of the crystal structure of biotin. Science 129, 210.
55. Uchegbu, I.F., Florence, A.T., 1995. Non-ionic surfactant vesicles (niosomes): physical and pharmaceutical chemistry. Adv. Colloid Interface Sci. 58, 1-55.
56. van Nunen, J.L.M., Stevens, R.S.A., Picken, S.J., Nolte, R.J.M., 1994. Tunable supramolecular structures from clips and baskets derived from glycoluril. J. Am. Chem. Soc. 116, 8825-8826.
57. Yager, P., Price, R.R., Schnur, J.M., Schoen, P.E., Singh, A., Rhodes, D.G., 1988. The mechanism of formation of lipid tubules from liposomes. Chem. Phys. Lipids 46, 171-179.
58. Yager, P., Schoen, P.E., 1984. Formation of tubules by a polymerizable surfactant. Mol. Cryst. Liq. Cryst. 106, 371-381.
59. Yamada, K., Ihara, H., Ide, T., Fukumoto, T., Hirayama, C., 1984. Formation of helical super structure from single-walled bilayers by amphiphiles with oligo-L-glutamic acid -head group. Chem. Lett. 1713-1716.
60. Zasadzinski, J.A.N., Schneir, J., Gurley, J., Elings, V., Hansma, P.K., 1988. Scanning tunneling microscopy of freeze-fracture replicas of biomembranes. Science 239, 1013-1015.
61. Zumbuehl, O., Weder, H.G., 1981. Liposomes of controllable size in the range of 40-180 nm by defined dialysis of lipid/detergent mixed micelles. Biochim. Biophys. Acta 640, 252-262.