Bolaamphiphilic phosphocholines: Structure and phase behavior in aqueous media

Langmuir

Volumn 16, Issue 1, 2000, Pages 128-133

  Di Meglio, Ciro ^a,b   Rananavare, Shankar B ^b   Svenson, Sönke ^a   Thompson, David H ^a  

^a PURDUE UNIVERSITY   (United States)

^b OREGON HEALTH AND SCIENCE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AIR; CHOLESTEROL; DISPERSIONS; GELS; LIQUID CRYSTALS; MELTING; MOLECULAR STRUCTURE; MONOLAYERS; PH; PHOSPHORUS COMPOUNDS; RAMAN SPECTROSCOPY; WATER;

BOLAAMPHIPHILIC PHOSPHOCHOLINES; SMALL ANGLE X RAY SCATTERING (SAXS);

SURFACE ACTIVE AGENTS;

EID: 0033876146     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la990627z     Document Type: Article

References (52)

1. Fuhrhop, J.-H.; Fritsch, D. Acc. Chem. Res. 1986, 19, 130.
2. Escamilla, G. H.; Newkome, G. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1937.
3. Zana, R. Curr. Opin. Colloid Interface Sci. 1996, 1, 566.
4. Yamauchi, K.; Moriya, A.; Kinoshita, M. Biochim. Biophys. Acta 1989, 1003, 151.
5. Yamauchi, K.; Sakamoto, Y.; Moriya, A.; Yamada, K.; Hosokawa, T.; Higuchi, T.; Kinoshita, M. J. Am. Chem. Soc. 1990, 112, 3188.
6. Kim, J.-M.; Thompson, D. H. Langmuir 1992, 8, 637.
7. Menger, F. M.; Chen, X. Y.; Brocchini, S.; Hopkins, H. P.; Hamilton, D. J. Am. Chem. Soc. 1993, 115, 6600.
8. Berkowitz, W. F.; Pan, D.; Bittman, R. Tetrahedron Lett. 1993, 34, 4297.
9. Thompson, D. H.; Svendsen, C. B.; Di Meglio, C.; Anderson, V. C. J. Org. Chem. 1994, 59, 2945.
10. Yamauchi, K.; Togawa, K.; Kinoshita,M. J. Biochem. 1996, 119, 115.
11. Eguchi, T.; Ibaragi, K.; Kakinuma, K. J. Org. Chem. 1998, 63, 2689.
12. Arakawa, K.; Eguchi, T.; Kakinuma, K. J. Org. Chem. 1998, 63, 4741.
13. Svenson, S.; Thompson, D. H. J. Org. Chem. 1998, 63, 7180.
14. Patwardhan, A.; Thompson, D. H. Org. Lett. 1999, 1, 241.
15. Fuhrhop, J.-H.; Spiroski, D.; Boettcher, C. J. Am. Chem. Soc. 1993, 115, 1600.
16. Schade, B.; Hubert, V.; Andre, C.; Luger, P.; Fuhrhop, J.-H. J. Peptide Res. 1997, 49, 363.
17. Kogiso, M.; Masuda, M.; Shimizu, T. Supramol. Chem. 1998, 9, 183.
18. Andre, D.; Luger, P.; Nehmzow, D.; Fuhrhop, J.-H. Carbohydr. Res. 1994, 261, 1.
19. Brisset, F.; Garelli-Calvet, R.; Azema, J.; Chebli, C.; Rico-Lattes, I.; Lattes, A.; Moisand, A. New J. Chem. 1996, 20, 595.
20. Pestman, J. M.; Terpstra, K. R.; Stuart, M. C. A.; van Doren, H. A.; Brisson, A.; Kellogg, R. M.; Engberts, J. B. F. N. Langmuir 1997, 13, 6857.
21. Bertho, J.-N.; Coué, A.; Ewing, D. F.; Goodby, J. W.; Letellier, P.; Mackenzie, G.; Plusquellec, D. Carbohydr. Res. 1997, 300, 341.
22. Shimizu, T.; Masuda, M. J. Am. Chem. Soc. 1997, 119, 2812.
23. Rivaux, Y., Noiret, N., Patin, H. New J. Chem. 1998, 22, 857.
24. Auzély-Velty, R.; Benvegnu, T.; Plusquellec, D.; Mackenzie, G.; Haley, J. A.; Goodby, J. W. Angew. Chem., Int. Ed. Engl. 1998, 37, 2511.
25. Boehme, P.; Hicke, H.-G.; Boettcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1995, 117, 5824.
26. Moss, R. A.; Li, J. M. J. Am. Chem. Soc. 1992, 114, 9227.
27. Bhattacharya, S.; De, S.; Subramanian, M. J. Org. Chem. 1998, 63, 7640.
28. Unusual diols with an H-shaped hydrocarbon domain have recently been isolated from a thermophilic methanogen: Morii, H.; Eguchi, T.; Nishihara, M.; Kakinuma, K.; König, H.; Koga, Y. Biochim. Biophys. Acta 1998, 1390, 339.
29. Bolaamphiphiles with regioisomeric glycerol backbones have been prepared: Eguchi, T.; Kano, H.; Kakinuma, K. Chem. Commun. 1996, 365.
30. Thompson, D. H.; Kim, J.-M. Mater. Res. Soc. Symp. Proc. 1992, 277, 93.
31. Thompson, D. H.; Kim, J.-M.; Di Meglio, C. SPIE Proc. 1993, 1853, 142.
32. Komatsu, T.; Yamada, K.; Tsuchida, E.; Siggel, U.; Böttcher, C.; Fuhrhop, J.-H. Langmuir 1996, 12, 6242.
33. Tsuchida, E.; Komatsu, T.; Fuhrhop, J.-H. Polym. Adv. Technol. 1998, 9, 569.
34. Komatsu, T.; Yanagimoto, T.; Tsuchida, E.; Siggel, U.; Fuhrhop, J.-H. J. Phys. Chem. B 1998, 102, 6759.
35. Hope, M. J.; Bally, M. B.; Webb, G.; Cullis, P. R. Biochim. Biophys. Acta 1985, 812, 55.
36. Moss, R. A.; Fujita, T.; Okumura, Y. Langmuir 1991, 7, 2415.
37. De Rosa, M. Thin Solid Films 1996, 284-285, 13.
38. Fyles, T. M.; Zeng, B. J. Org. Chem. 1998, 63, 8337.
39. Mingotaud, A.-F.; Mingotaud, C.; Patterson, L. K. Handbook of Monolayers; Academic Press: San Diego, CA, 1993; Vol. 1, pp 778-804.
40. 25
41. Luzzati, V.; Gulik-Krzwicki, T.; Tardieu, A. Nature 1968. 218, 1031.
42. w are the partial specific volumes for the lipid and the interlamellar water, respectively.
43. (b) Marsh, D. Handbook of Lipid Bilayers; CRC Press, Inc.: Boca Raton, FL, 1990; pp 163-173.
44. A is Avogadro's number, and z is 1 for monolayer lamella and 2 for bilayer structures.
45. (b) Marsh, D. General Features Of Phospholipid Phase-Transitions. Chem. Phys. Lipids 1991, 57, 109.
46. Thompson, D. H.; Wong, K. F.; Humphry-Baker, R.; Wheeler, J. J.; Kim, J.-M.; Rananavare, S. B. J. Am. Chem. Soc. 1992, 114, 9035.
47. Bhattacharya, S.; De, S.; George, S. K. Chem. Commun. 1997, 2287.
48. Gliozzi, A.; Robello, M.; Relini, A.; Accardo, G. Biochim. Biophys. Acta 1994, 1189, 96.
49. Quantities reported for the hexadecyl derivative were averaged over four different published values, whereas values for the eicosyl derivative were estimated; see: Marsh, D. Handbook of Lipid Bilayers; CRC Press: Boca Raton, FL, 1990; pp 138 and 149.
50. Levin, I. W. In Advances in Infrared and Raman Spectroscopy; Clark, R. J. H., Hester, R. E., Eds.; Wiley: Heyden, 1984; Vol. 11, pp 1-48.
51. An asymmetric distribution of U-shaped conformations, with a greater proportion of them necessary on the outer surface to accommodate the surface area mismatch between the inner and outer surfaces, is required to form highly curved vesicles with diameters ≤ 0.1 μm.
52. Patwardhan, A.; Di Meglio, C.; Rananavare, S. B.; Svenson, S.; Haynes, R.; Thompson, D. H. Unpublished results.