Advertisement

Modulation of Phosphocholine Bilayer Structures

  • Alok Singh
  • Michael A. Markowitz
  • Li-I Tsao

Abstract

Vesicles derived from phosphocolines have been used in the encapsulation, retention and release of biomaterials. Diacetylenic phospholipids in aqueous dispersions are reported to transform into rigid, hollow cylindrical structures (0.5-0.8 pm diameter and length depending on the process) or tubules and helices. Tubules are used in the encapsulation and sustained release of bioactive materials. Synthesis of two diacetylenic phosphocholines, l,2-bis-(9,16-dioxahexacosa-11,13-diynoic)-sn-3-phosphocholine and 1,2-bis(15-oxa-pentacosa-10,12-diynoic)-sn-3-phosphocholine, in which the diacetylene is linked to the acyl chain by an oxygen spacer is reported to modulate the morphology of bilayer structures and to understand the role of diacetylene in lipid-bilayer assembly. Lipid dispersions were characterized by calorimetric and film balance techniques and the structures were visualized by microscopic techniques. When both ends of the diacetylene were linked to the acyl chain by oxygen atoms, vesicles (diameters ranging from 0.3-3.4 pm) were observed. Linking only the terminal portion of the acyl chain to the diacetylene with an oxygen atom resulted in the formation of tubular microstructures with a diameter ranged from 0.4-4.7 pm. Transmission electron micrograph of the replica of freeze fractured dispersion revealed that the tubular structures consist of an aqueous core surrounded by a wall of lipid.

Keywords

Acyl Chain Melting Transition Aqueous Sodium Hydroxide Propargyl Alcohol Lipid Dispersion 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    D. Chapman, Biological Membranes, Academic Press, London (1968).Google Scholar
  2. 2.
    R. R. C. New, “Liposomes, a Practical Approach, Oxford University Press, New York (1990).Google Scholar
  3. 3.
    P. Yager and P. E. Schoen, P.E., Mol. Cryst. Liq. Cryst. 106, 371 (1984).CrossRefGoogle Scholar
  4. 4.
    J. H. Georger, A. Singh, R. R. Price, J. M. Schnur, P. Yager and P. E. Schoen, J. Amer. Chem. Soc., 109, 6169 (1987).CrossRefGoogle Scholar
  5. 5.
    P. Yager, P. Schoen, C. Davies, R. Price and A. Singh, Biophys. J., 48, 899 (1985).PubMedCrossRefGoogle Scholar
  6. 6.
    B. P. Gaber, J. M. Schnur and D. Chapman, Eds., “Biotechnological Applications of Lipid Microstructures, Plenum Press, New York, pp. 305–320 (1988).Google Scholar
  7. 7.
    T. G. Burke, A. Singh and P. Yager, Ann. N. Y. Acad. Sci. 507, 330 (1987).CrossRefGoogle Scholar
  8. 8.
    J. M. Schnur, P. Yager, R. Price, J. M. Calvert, P. E. Schoen and J. H. Georger, U.S. Patent 4,911, 981 (1990).Google Scholar
  9. 9.
    F. Behroozi, M. Orman, W. Stockton, J. Calvert, F. Rochford and P. E. Schoen, J. Appl. Phys., 68, 3688 (1990).CrossRefGoogle Scholar
  10. 10.
    P. G. de Gennes, C.R. Seances Acad. Sci., 304, 259 (1987).Google Scholar
  11. 11.
    W. Helfrich and J. Prost, Phys. Rev., A38, 3065 (1988).CrossRefGoogle Scholar
  12. 12.
    J. N. Israelachvili, “Intermolecular and Surface Forces, Academic Press, New York (1985).Google Scholar
  13. 13.
    J. C. Chappel and P. Yager, Chem. Phys. Lipids, 58, 253 (1991).CrossRefGoogle Scholar
  14. 14.
    A. Singh, T. G. Burke, J. M. Calvert, J. H. Georger, B. Herendeen, R. R. Price, P. E. Schoen and P. Yager, Chem. Phys. Lipids, 47, 135 (1988).CrossRefGoogle Scholar
  15. 15.
    A. Singh, P. E. Schoen and J. M. Schnur, J. Chem. Soc., Chem. Commun., 1222 (1988).Google Scholar
  16. 16.
    S. L. Blechner, W. Morris, P. E. Schoen, P. Yager, A. Singh and D. G. Rhodes, Chem. Phys. Lipids, 58, 41 (1991).CrossRefGoogle Scholar
  17. 17.
    T. G. Burke, A. S. Rudolph, R. R. Price, J. P. Sheridan, A. W. Dalziel, A. Singh and P. E. Schoen, Chem. Phys. Lipids, 48, 215 (1988).PubMedCrossRefGoogle Scholar
  18. 18.
    A. Singh, B. P. Singh, B. P. Gaber, R. Price, T. G. Burke, B. Herendeen, P. E. Schoen, J. M. Schnur and P. Yager, in: “Surfactants in Solution, K. L. Mittal, Ed., Plenum Press, New York, 8, 467 (1989).Google Scholar
  19. 19.
    A. S. Rudolph, B. P. Singh, A. Singh and T. G. Burke, Biochim. Biophys. Acta 943, 454 (1988).CrossRefGoogle Scholar
  20. 20.
    P. Yager, R. R. Price, J. M. Schnur, P. E. Schoen, A. Singh and D. Rhodes, Chem. Phys. Lipids 46, 171 (1988).CrossRefGoogle Scholar
  21. 21.
    P. Schoen, P. Yager, J. P. Sheridan, R. Price, J. M. Schnur, A. Singh, D. G. Rhodes and S. L. Blechner, Mol. Cryst. Liq. Cryst. 153, 357 (1987).Google Scholar
  22. 22.
    A. Singh and M. A. Markowitz, in: “Membrane Structure and Functions-The State of the Art, B. P. Gaber and K. R. K. Easwaran, Eds., Adenine Press, New York, 1992, p 37.Google Scholar
  23. 23.
    A. Singh and S. Marchywka, Polym. Mat. Sci. Eng., 61, 675 (1989).Google Scholar
  24. 24.
    M. Markowitz and A. Singh, Langmuir, 7, 16 (1991).CrossRefGoogle Scholar
  25. 25.
    M. A. Markowitz, J. M. Schnur and A. Singh, in: “Synthetic Microstructures in Biological Research,” J. M. Schnur and M. Peckarar Eds., Plenum Publishing, New York, 1992, in press.Google Scholar
  26. 26.
    M. A. Markowitz, J. M. Schnur and A. Singh, Chem. Phys. Lipids, 62, 193 (1992).CrossRefGoogle Scholar
  27. 27.
    R. Price and M. Patchan, J. Microencap., 8, 301 (1991).CrossRefGoogle Scholar
  28. 28.
    R. Price and M. Patchan, J. Microencap., (1992) in press.Google Scholar
  29. 29.
    A. S. Rudolph, A. Singh, R. Price, B. Goins and B. Gaber, in: “Fundamentals and Applications in Targeting of Drugs, G. Gregoridis, et al., Eds, Plenum Press, New York, p 103 (1990).Google Scholar
  30. 30.
    A. Singh, J. Lipid Res., 31, 1522 (1990).PubMedGoogle Scholar
  31. 31.
    D. Johnston, S. Sanghera, M. Pons and D. Chapman, Biochim. Biophys. Acta, 602, 57 (1980).CrossRefGoogle Scholar
  32. 32.
    A. Singh and J. M. Schnur, Synth. Commun., 16, 847 (1986).CrossRefGoogle Scholar
  33. 33.
    D. J. Johnston, L. R. Mclean, M. A. Wittman, A. D. Clark and D. Chapman, Biochemistry, 22, 3194 (1983).PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1994

Authors and Affiliations

  • Alok Singh
    • 1
  • Michael A. Markowitz
    • 1
  • Li-I Tsao
    • 1
  1. 1.Center for Bio/Molecular Science and Engineering Code 6900Naval Research LaboratoryUSA

Personalised recommendations