Abstract
For the liposome of two types of phospholipids (zwitterionic dipalmitoyl-phosphatidylcholine (DPPC) and anionic dimyristoylphosphatidic acid (DMPA)), the partition coefficient K X for partition of homologous ω-phenylalkanols (C6H5(CH2) mp OH; m p =0–8) between bulk water and the liposome membrane was determined on the basis of the gel to liquid crystalline phase transition temperature T m of the liposome membrane. The plot of log K X vs. m p gave a break at m p =7 for both phospholipids, and a second break at m p =4 was observed for DPPC. The local polarity of the surface region and the orderliness of phospholipid molecules in the liposome membrane were estimated from ESR spectra of two spin probes solubilized in the membrane. The results suggest that the hydration of DPPC liposome membrane is relatively restricted to its surface region, but for DMPA the hydration spreads not only along the surface but also to the inside of the membrane. The main factor controlling the partitioning of the alkanols is the local polarity. The higher alkanols (m p =7, 8) are solubilized not only in the liquid crystalline phase but also in the gel phase, although the other lower alkanols are solubilized in the liquid phase only.
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References
M. W. Hill,Biochim. Biophys. Acta 356, 117 (1974).
H. Kamaya, S. Kaneshina, and I. Ueda,Biochim. Biophys. Acta 646, 135 (1981).
E. S. Rowe,Biochemistry 22, 3299 (1983).
A. G. Lee,Biochemistry 15, 2448 (1976).
P. Seeman,Phamacol. Rev. 24, 583 (1972).
H. Kamaya, N. Matsubayashi, and I. Ueda,J. Phys. Chem. 88, 797 (1984).
M. J. Pringle and K. W. Miller,Biochemistry 18, 3314 (1979).
E. S. Rowe,Mol. Pharmacol. 22, 130 (1982).
J. R. Trudell, W. L. Hubbell, and E. N. Cohen,Biochim. Biophys. Acta 291, 328 (1973).
T. Yamaguchi, M. Koga, Y. Fujita, and E. Kimoto,J. Biochem. 91, 1299 (1982).
H. H. Wang, J. Earnest, and H. P. Limbacher,Proc. Natl. Acad. Sci. U. S. A. 80, 5297 (1983).
J. D. Castle and W. L. Hubbell,Biochemistry 15, 4818 (1976).
M. Manabe, K. Shirahama, and M. Koda,Bull. Chem. Soc. Jpn. 49, 2904 (1976).
A. S. Waggoner, A. D. Keith, and O. H. Griffith,J. Phys. Chem. 72, 4129 (1968).
T. Inoue, K. Miyakawa, and R. Shimozawa,Chem. Phys. Lipids 42, 261 (1986).
D. Marsh,CRC Handbook of Lipid Bilayers (CRC Press, 1990).
H. Kawamura, M. Manabe, Y. Miyamoto, Y. Fujita, and S. Tokunaga,J. Phys. Chem. 93, 5536 (1989).
B. R. Knauer and J. J. Napier,J. Am. Chem. Soc. 98, 4395 (1976).
H. Yoshioka,J. Am. Chem. Soc. 101, 28 (1979).
M. F. Ottaviani, P. Baglioni, and G. Martini,J. Phys. Chem. 87, 3146 (1983).
P. Baglioni, E. R. Minten, L. Dei, and E. Ferroni,J. Phys. Chem. 94, 8218 (1990).
S. Ristori and G. Martini,Langmuir 8, 1937 (1992).
F. M. Menger,Acc. Chem. Res. 12, 111 (1979).
S. Schreier-Muccillo, D. Marsh, H. Dugas, H. Schneider, and I. C. P. Smith,Chem. Phys. Lipids 10, 11 (1973).
H. Kawamura, M. Manabe, T. Tokunoh, H. Saiki, and S. Tokunaga,J. Solution Chem. 20, 817 (1991).
M. Manabe, H. Kawamura, G. Sugihara, and M. Tanaka,Bull. Chem. Soc. Jpn. 61, 1551 (1988).
T. Inoue, K. Fukushima, and R. Shimozawa,Bull. Chem. Soc. Jpn. 61, 1565 (1988).
H. Kawamura, M. Manabe, H. Saiki, and S. Tokunaga,Mem. Niihama Natl. Coll. Tech. 28, 84 (1992).
M. Abu-Hamdiyyah,J. Phys. Chem. 90, 1345 (1986).
R. F. Rekker,The Hydrophobic Fragmental Constant (Elsevior, 1977).
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Kawamura, H., Manabe, M., Yamashita, R. et al. Partition coefficients of ω-phenylalkanols between water and liposome membranes of phospholipids. J Solution Chem 23, 85–100 (1994). https://doi.org/10.1007/BF00972611
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DOI: https://doi.org/10.1007/BF00972611