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.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
D. Chapman, Biological Membranes, Academic Press, London (1968).
R. R. C. New, “Liposomes, a Practical Approach,” Oxford University Press, New York (1990).
P. Yager and P. E. Schoen, P.E., Mol. Cryst. Liq. Cryst. 106, 371 (1984).
J. H. Georger, A. Singh, R. R. Price, J. M. Schnur, P. Yager and P. E. Schoen, J. Amer. Chem. Soc., 109, 6169 (1987).
P. Yager, P. Schoen, C. Davies, R. Price and A. Singh, Biophys. J., 48, 899 (1985).
B. P. Gaber, J. M. Schnur and D. Chapman, Eds., “Biotechnological Applications of Lipid Microstructures,” Plenum Press, New York, pp. 305–320 (1988).
T. G. Burke, A. Singh and P. Yager, Ann. N. Y. Acad. Sci. 507, 330 (1987).
J. M. Schnur, P. Yager, R. Price, J. M. Calvert, P. E. Schoen and J. H. Georger, U.S. Patent 4,911, 981 (1990).
F. Behroozi, M. Orman, W. Stockton, J. Calvert, F. Rochford and P. E. Schoen, J. Appl. Phys., 68, 3688 (1990).
P. G. de Gennes, C.R. Seances Acad. Sci., 304, 259 (1987).
W. Helfrich and J. Prost, Phys. Rev., A38, 3065 (1988).
J. N. Israelachvili, “Intermolecular and Surface Forces,” Academic Press, New York (1985).
J. C. Chappel and P. Yager, Chem. Phys. Lipids, 58, 253 (1991).
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).
A. Singh, P. E. Schoen and J. M. Schnur, J. Chem. Soc., Chem. Commun., 1222 (1988).
S. L. Blechner, W. Morris, P. E. Schoen, P. Yager, A. Singh and D. G. Rhodes, Chem. Phys. Lipids, 58, 41 (1991).
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).
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).
A. S. Rudolph, B. P. Singh, A. Singh and T. G. Burke, Biochim. Biophys. Acta 943, 454 (1988).
P. Yager, R. R. Price, J. M. Schnur, P. E. Schoen, A. Singh and D. Rhodes, Chem. Phys. Lipids 46, 171 (1988).
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).
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.
A. Singh and S. Marchywka, Polym. Mat. Sci. Eng., 61, 675 (1989).
M. Markowitz and A. Singh, Langmuir, 7, 16 (1991).
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.
M. A. Markowitz, J. M. Schnur and A. Singh, Chem. Phys. Lipids, 62, 193 (1992).
R. Price and M. Patchan, J. Microencap., 8, 301 (1991).
R. Price and M. Patchan, J. Microencap., (1992) in press.
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).
A. Singh, J. Lipid Res., 31, 1522 (1990).
D. Johnston, S. Sanghera, M. Pons and D. Chapman, Biochim. Biophys. Acta, 602, 57 (1980).
A. Singh and J. M. Schnur, Synth. Commun., 16, 847 (1986).
D. J. Johnston, L. R. Mclean, M. A. Wittman, A. D. Clark and D. Chapman, Biochemistry, 22, 3194 (1983).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1994 Springer Science+Business Media New York
About this chapter
Cite this chapter
Singh, A., Markowitz, M.A., Tsao, LI. (1994). Modulation of Phosphocholine Bilayer Structures. In: Gebelein, C.G., Carraher, C.E. (eds) Biotechnology and Bioactive Polymers. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-9519-6_13
Download citation
DOI: https://doi.org/10.1007/978-1-4757-9519-6_13
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4757-9521-9
Online ISBN: 978-1-4757-9519-6
eBook Packages: Springer Book Archive