Stereodependent fusion and fission of vesicles: Calcium binding of synthetic gemini phospholipids containing two phosphate groups

Journal of the American Chemical Society

Volumn 119, Issue 19, 1997, Pages 4338-4344

  Sommerdijk, N A J M ^a   Hoeks, T H L ^a   Synak, M ^a   Feiters, M C ^a   Nolte, R J M ^a   Zwanenburg, B ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHOLIPID;

ARTICLE; CALCIUM BINDING; ISOMERISM; MEMBRANE BINDING; MEMBRANE FUSION; MEMBRANE VESICLE; PHOSPHOLIPID MEMBRANE; STEREOCHEMISTRY;

EID: 0030945764     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962303s     Document Type: Article

References (53)

1. (a) Gingel, D.; Ginsberg, L. In Cell Surface Rev. Poste, G., Nicolson, G. L., Eds.; North Holland, Amsterdam, 1978; Vol. 5, pp 791-833.
2. (b) Cullis, P. R; de Kruijff, B. Biochim. Biophys. Acta 1979, 559, 399.
3. (c) Molecular mechanisms of membrane fusion; Ohki, S., Doyle, D., Flanagan, T. D., Hui, S. W., Mayhew, E., Eds.; Plenum: New York, 1988.
4. Ohnishi, T.; Ito, T. Biochemistry 1974, 13, 881.
5. (a) Verkleij, A. J.; De Kruyff, B.; Ververgaert, P. H. J. Ph.; Tocanne, J. F.; van Deenen, L. L. M. Biochim. Biophys. Acta 1974, 339, 432.
6. (b) Papahadjopoulos, D.; Jacobson, K.; Vail, W. J.; Poste, G. Biochim. Biophys. Acta 1975, 394, 483.
7. (c) Papahadjopoulos, D.; Vail, W. J.; Pangborn, W. A.; Poste, G. Biochim. Biophys. Acta 1976, 448, 265.
8. (d) Dluhy, R. A.; Cameron, D. G.; Mantsch, H. H.; Mendelsohn, R. Biochemistry 1983, 22, 6318.
9. (e) Verkleij, A. J. Biochim. Biophys. Acta 1984, 779, 43.
10. (f) Nakashima, N.; Ando, R.; Fukushima, H.; Kunitake, T. Chem. Lett. 1985, 1503.
11. (g) Siegel, D. P. Biophys. J. 1986, 49, 1171.
12. (h) Casal, H. L.; Marin, A.; Mantsch, H. H.; Paltauf, F.; Hauser, H. Biochemistry 1987, 26, 4408.
13. (i) Casal, H. L.; Mantsch, H. H.; Hauser, H. Biochemistry 1987, 26, 7395.
14. (j) Casal, H. L.; Mantsch, H. H.; Hauser, H. Biochim. Biophys. Acta 1989, 982, 228.
15. (a) Rupert, L. A. M.; van Breemen, J. F. L.; van Bruggen, E. F. J.; Engberts, J. B. F. N. Hoekstra, D. J. Membrane Biol. 1987, 95, 225.
16. (b) Wagenaar, A.; Streefland, L.; Hoekstra, D.; Engberts, J. B. F. N. J. Phys. Org. Chem. 1992, 5, 451.
17. (c) Streefland, L. Wagenaar, A. Hoekstra, D. Engberts, J. B. F. N. Langmuir 1993, 9, 219.
18. (a) Rupert, L. A. M.; Engberts, J. B. F. N.; Hoekstra, D. J. Am. Chem. Soc. 1986, 107, 2628.
19. (b) Rupert, L. A. M.; Engberts, J. B. F. N.; Hoekstra, D. J. Am. Chem. Soc. 1986, 108, 3920.
20. (c) Menger, F. M.; Balachander, N. J. Am. Chem. Soc. 1992, 114, 5862.
21. (d) Menger, F. M.; Gabrielson, K. J. Am. Chem. Soc. 1994, 11, 1567.
22. (e) Menger, F. M.; Gabrielson, K. D Angew. Chem. 1995, 107, 2260.
23. Wick, R.; Wade, P.; Luisi, P. L. J. Am. Chem. Soc. 1995, 117, 1435.
24. Borggreven, J. M. P. M.; Hoeks, T. H. L.; Driessens, F. C. M.; Zwanenburg, B. Caries Res. 1992, 26, 84.
25. (a)Menger, F. M.; Littau, C. A. J. Am. Chem. Soc. 1993, 115, 10083.
26. (b) Karaborni, S.; Esselink, K.; Hilbers, P. A. J.; Smit, B.; Karthäuser, J.; van Os, N. M.; Zana, R. Science 1994, 266, 254.
27. (a) Fischer, E. Ber. 1920, 53, 1621.
28. (b) Doerschuk, A. P. J. Am. Chem. Soc. 1952, 74, 4202.
29. (c) van Lohuizen, O. E.; Verkade, P. E. Recl. Trav. Chim. Pays-Bas 1960, 79, 133.
30. (d) Serdavich, B. J. Am. Oil Chem. Soc. 1967, 44, 1.
31. (a) Brown, D. M.; Magrath, D. I.; Todd, A. R. J. Chem. Soc. 1955, 4396.
32. (b) de Rooy, J. F. M.; Wille-Hazeleger, G.; Burgers, P. M. J.; Van Boom, J. H. Nucleic Acids Res. 1979, 6, 2237.
33. Carmack, M.; Kelly, C. J. J. Org. Chem. 1968, 33, 2171.
34. Seebach, D.; Hungerbühler, E. Modem Synthetic Methods; Sheffold, R., Ed.; Otto Salle Verlag, Frankfort/Munich 1980; Vol. 2, p 155.
35. Rubin, L. J.; Lardy, H. A.; Fischer, H. O. L. J. Am. Chem. Soc. 1952, 74, 425.
36. Direct iodination of 1,4-ditosyl erythritol led to the formation of 1-iodo-3,4-buten-2-ol (see, also: House, H. O.; Ro, R. S. J. Am. Chem. Soc. 1958, 80, 182. Cristol, S. J.; Rademacher, L. E. J. Am. Chem. Soc. 1959, 81, 1600.)
37. Direct iodination of 1,4-ditosyl erythritol led to the formation of 1-iodo-3,4-buten-2-ol (see, also: House, H. O.; Ro, R. S. J. Am. Chem. Soc. 1958, 80, 182. Cristol, S. J.; Rademacher, L. E. J. Am. Chem. Soc. 1959, 81, 1600.)
38. (a) Szarek, W. A.; Zamojski, A.; Tiwari, K. M.; Ison, E. R. Tetrahedron Lett. 1986, 3827.
39. (b) Verhart, C. G. J.; Caris, B. M. G.; Zwanenburg, B.; Chittenden, G. J. F. Rec. Trav. Chim. Pays-Bas 1992, 110, 348.
40. Zervas, L. Naturwiss. 1939, 27, 317.
41. 3 as a chiral shift reagent. Methylation was accomplished by reaction of the free acid of 1a,b with diazomethane. Enantiomeric splitting of the methyl signals revealed an optical purity of at least 95%.
42. Sommerdijk, N. A. J. M.; Feiters, M. C.; Nolte, R. J. M.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1994, 113, 194.
43. Control experiments were performed using 1a. These experiments revealed that this compound also exhibits vesicle fusion upon addition of calcium ions.
44. (a) Hénon, S.; Meunier, J. Rev. Sci. Intrum. 1991, 62, 936.
45. (b) Hönig, D.; Möbius, D. J. Phys. Chem. 1991, 95, 4590.
46. These events have been observed in reversed order for the fusion of ammonium surfactants. See ref 5d.
47. The reflection in the 4.0-4.5 Å region represents the side of a cell in the hexagonal lattice in which the hydrocarbon chains are packed. For both compounds a broadening in this reflection is observed after addition of calcium ions. This is indicative of a distorted hydrocarbon chain packing see: (a) Gulik-Krzywicki, T.; Rivas, E.; Luzzati, V. J. Mol. Biol. 1967, 27, 303.
48. (b) Tardieu, A.; Luzzati, V. J. Mol. Biol. 1973, 75, 711.
49. (c) Ranck, J. L.; Mathieu, L.; Sadler, D. M.; Tardieu, A.; Gulik-Krzywicki,; T. Luzzati, V. J. Mol. Biol. 1974, 85, 249. This decrease in organization in the interior of the membrane is also in agreement with the change in transition entropy deduced from the DSC data (Table 1).
50. Dittmer, J. C. Lester, R. L. J. Lipid Res. 1964, 5, 126.
51. Knight, R. H.; Young, L. Biochem. J. 1981, 70, 111.
52. This melting point range suggests the presence of impurities. They could not be removed despite several attempts to obtain analytically pure material. It was then decided to purify the compound at a later stage in the synthetic sequence.
53. 4 buffer of pH = 3).