Summary
Polymerizable glycerophosphocholines containing one or two 2,4-hexadienyloxy groups at the terminal of the acyl chains were prepared. Those were 1-[11-(2,4-hexadienyloxy)undecanoyl]-2-0-alkyl-rac-glycero-3-phosphocholines 1, 1-acyl-2-[11-(2,4-hexadienyloxy)undecanoyl]-sn-glycero-3-phosphocholines 2 and 1,2-bis[11-(2,4-hexadienyloxy)undecanoyl]-sn-glycero-3-phosphocholine 3. Those having one hexadienyloxy group formed small unilamellar vesicles. One having two groups formed lipid bilayers, but not unilamellar vesicles. 1 and 2 could form stable microcapsules (polymerized vesicles) with the diameters ranging from 20 to 40 nm.
Similar content being viewed by others
References
This forms part 4 of a series entitled “Synthesis and Properties of Polymerizable Phospholipids”.
G. Gregoriadis, “Drug Carriers in Biology and Medicine”, Academic Press, London (1979).
J. H. Fendler, “Membrane Mimetic Chemistry”, John Wiley and Sons, New York (1984).
D. A. Tirrell, L. G. Donaruma and A. B. Turek, eds., “Macromolecules as Drugs and as Carriers for Biologically Active Materials”, The New York Acad. Sci., New York (1985).
T. Kunitake and Y. Okahata, J. Amer. Chem. Soc. 99, 3860 (1977).
D. Day, H. H. Hub and H. Ringsdorf, Isr. J. Chem. 18, 325 (1979).
S. L. Regen, A. Singh, G. Oehme and M. Singh, Biochem. Biophys. Res. Commun. 101, 131 (1981).
D. S. Johnston, S. Sanghera, A. Manjon-Rubio and D. Chapman, Biochim. Biophys. Acta 602, 213 (1980).
L. Gros, H. Ringsdorf and H. Schupp, Angew. Chem. Int. Ed. Engl. 20 305 (1982).
E. Lopez, D. F. O'Brien and T. H. Whitesides, J. Amer. Chem. Soc. 104, 305 (1981).
S. L. Regen, A. Singh, G. Oehme and M. Singh, ibid, 104, 791 (1982).
E. Hasegawa, Y. Matsushita, K. Eshima, H. Nishide and E. Tsuchida, Makromol. Chem. Rapid Commun. 5, 779 (1984).
E. Hasegawa, K. Eshima, Y. Matsushita, H. Nishide and E. Tsuchida, Polymer Bull. 14, 31 (1985).
E. Hasegawa, K. Eshima, Y. Matsushita, H. Nishide and E. Tsuchida, Synthesis in contribution (1986).
D. Arnold, H. U. Weltzien and O. Westphal, Justus Liebigs, Ann. Chem. 709, 234 (1967).
R. S. Edmundson, Chem. Ind. (London) 1828 (1962).
V. F. Bystrov, N. I. Dubrovina, L. I. Bardukov and L. D. Bergelson, Chem. Phys. Lipids 6, 343 (1971).
S. B. Andrews, J. W. Faller, J. M. Gillian and R. J. Barrnett, Proc. Nat. Acad. Sci. USA 70, 1814 (1973).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Hasegawa, E., Matsushita, Yi., Eshima, K. et al. Polymerizable glycerophosphocholines containing terminal 2,4-hexadienyloxy groups and their polymerized vesicles(1) . Polymer Bulletin 15, 397–403 (1986). https://doi.org/10.1007/BF00265720
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00265720