Synthetic glycolipids as membrane-bound cryoprotectants in the freeze-drying process of liposomes

European Journal of Pharmaceutical Sciences

Volumn 4, Issue 4, 1996, Pages 211-222

  Bendas, Gerd ^a   Wilhelm, Falk ^a   Richter, Walter ^b   Nuhn, Peter ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Freeze frying; Fusion; Glycolipid; Lectin; Liposome

Indexed keywords

6 CARBOXYFLUORESCEIN; CARBOHYDRATE; CELLOBIOSE; CRYOPROTECTIVE AGENT; GALACTOSE; GLYCOLIPID; LECTIN; LIPOSOME;

ARTICLE; CHEMICAL STRUCTURE; ENCAPSULATION; FREEZE DRYING; HYDRATION; MEMBRANE STABILIZATION; PARTICLE SIZE; PRIORITY JOURNAL; SURFACE PROPERTY;

EID: 0030006583     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/0928-0987(95)00054-2     Document Type: Article

References (31)

1. Crowe, J.H., Crowe, L.M. and Chapman, D. (1984) Infrared spectroscopic studies on interactions of water and carbohydrates with a biological membrane. Arch. Biochem. Biophys. 232, 400-407.
2. Crowe, J.H., Crowe, L.M., Carpenter, J.F., Rudolph, A.S., Wistrom, C.A., Spargo, B.J. and Anchordoguy, T.J. (1988) Interactions of sugars with membranes. Biochim. Biophys. Acta 947, 367-384.
3. Crowe, J.H., Leslie, S.B. and Crowe, J.H. (1994) Is vitrification sufficient to preserve liposomes during freeze-drying. Cryobiology 31, 355-366.
4. Crowe, L.M., Womersley, C,Z., Crowe, J.H., Reid, D., Appel, L. and Rudolph, A. (1986) Prevention of fusion and leakage in freeze dried liposomes by carbohydrates. Biochim. Biophys. Acta 861, 131-140.
5. Curatolo, W. (1987) The physical properties of glycolipids. Biochim. Biophys. Acta 906, 111-136.
6. Düzgünes, N., Allen, T.M., Fedor, J. and Papahadjopoulos, D. (1987) Lipid mixing during membrane aggregation and fusion: Why fusion assays disagree. Biochemistry 26, 8435-8442.
7. Engel, A., Bendas, G., Wilhelm, F., Mannova, M., Ausborn, M. and Nuhn, P. (1994) Freeze drying of liposomes with free and membrane-bound cryoprotectants-the backround of protection and damaging processes. Int. J. Pharmac. 107, 99-110.
8. Förster, G., de la Cruz Rodriguez, O., Bendas, G. and Nuhn, P. (1995) The influence of single chain anchored galactose on the polymorphism of resuspended lyophilized DPPC liposomes. Progr. Colloid Polym. Sci. 98, 201-205.
9. Franks, F. (Ed.) (1985) Biophysics and Biochemistry at Low Temperatures. Cambridge University Press, Cambridge, pp. 21-36.
10. Goodrich, R.P. and Baldeschwieler, J.D. (1991) The cryoprotective action of synthetic glycolipids. Cryobiology 28, 327-334.
11. Goodrich, R.P., Crowe, J.H., Crowe, L.M. and Baldeschwieler, J.D. (1991) Alterations in membrane surfaces induced by attachment of carbohydrates. Biochemistry 30, 5313-5318.
12. Grant, C.W.M. and Peters, M.W. (1984) Lectin-membrane interactions; Information from model systems. Biochim. Biophys. Acta 779, 403-422.
13. Harrigan, P.R., Madden, T.D. and Cullis, P.R. (1990) Protection of liposomes during dehydration or freezing. Chem. Phys. Lipids 52, 139-149.
14. Higa, L.M. and Womersley, C.Z. (1993) New insight into the anhydrobiotic phenomenon: The effects of trehalose content and differential rates of evaporative water loss on the survival of Aphelenchus avenae. J. Exp. Zool. 267, 120-129.
15. Hinz, H.J., Kuttenreich, H., Meyer, R., Renner, M. and Fründ, R. (1991) Stereochemistry and size of sugar head groups determine structure and phase behavior of glycolipid membranes: Densitometric, calorimetric and X-ray studies. Biochemistry 30, 5125-5138.
16. Koster, K.L., Webb, M.S., Bryant, G. and Lynch, D.V. (1994) Interactions between soluble sugars and POPC (1-palmitoyl-2-oleoylphophatidylcholine) during dehydration: vitrification of sugars alters the phase behavior of the phospholipid. Biochim. Biophys. Acta 1193, 143-150.
17. Levine, H. and Slade, L. (1988) Principles of "cryostabilization" technology from structure/property relationships of carbohydrate/ water systems - A review. Cryo-Letters 9, 21-63.
18. Madden, T.D., Bally, M.B., Hope, M.J., Cullis, P.R., Schieren, H.P. and Janoff, A.S. (1985) Protection of large unilamellar vesicles by trehalose during dehydration: retention of vesicle contents. Biochim. Biophys. Acta 817, 356-362.
19. Madin, K.A.C. and Crowe, J.H. (1975) Anhydrobiosis in nematodes: Carbohydrate and lipid metabolism during dehydration. J. Exp. Zool. 193, 335-342.
20. Nuhn, P., Pfaff, T., Bendas, G., Wilhelm, F. and Chatterjee, S.-K. (1994) Infrarotspektroskopische Untersuchungen an lyophilisierten Liposomen zur Charakterisierung der Wechselwirkungen von freien und membrangebundenen Zuckern mit Phospholipiden. Arch. Pharm. 327, 429-433.
21. Ogawa, T., Beppu, K. and Nakabayashi, S. (1981) Trimethylsilyl trifluoromethansulfonate as an effective catalyst for glycoside synthesis. Carbohydr. Res. 93, C6-C9.
22. Park, Y.S. and Huang, L. (1992a) Cryoprotective activity of synthetic glycophospholipids and their interactions with trehalose. Biochim. Biophys. Acta 1124, 241-248.
23. Park, Y.S. and Huang, L. (1992b) Interactions of synthetic glycophospholipids with phospholipid bilayers. Biochim. Biophys. Acta 1112, 251-258.
24. Sakai, H., Takisada, M., Takeoka, S. and Tsachida, E., (1993) Cryoprotection of synthetic glycolipids for phospholipid vesicles. Chem. Lett. 1891-1894.
25. Slama, J.S. and Rando, R.R. (1980) Lectin-mediated aggregation of liposomes containing glycolipids with variable hydrophilic spacer arms. Biochemistry 19, 4595-4600.
26. Struck, K.D., Hoeckstra, D. and Pagano, E. (1981) Use of resonance energy transfer to monitor membrane fusion. Biochemistry 20, 4093-4099.
27. Testoff, M.A. and Rudolph, A.S. (1992) Modification of dry 1,2-dipalmitoylphosphatidylcholine phase behavior with synthetic membrane-bound stabilizing carbohydrates. Bioconj. Chem. 3, 203-211.
28. Tsvetkova, N., Tenchov, B., Tsonev, L. and Tsvetkov, T.D. (1988) Dependence of trehalose protective action on the initial phase state of dipalmitoylphosphatidylcholine bilayers. Cryobiology 25, 256-263.
29. Tsvetkov, T.D., Tsonev, L.I., Tsvetkova, N.M., Koynowa, R.D. and Tenchov, B.G. (1989) Effect of trehalose on the phase properties of hydrated and lyophilized dipalmitoylphosphatidylcholine multilayers. Cryobiology 26, 162-169.
30. Womersley, C., Uster, P.S., Rudolph, A.S. and Crowe, J.H. (1986) Inhibition of dehydration-induced fusion between liposomal membranes by carbohydrates as measured by fluorescence energy transfer. Cryobiology 23, 245-255.
31. Yoshioka, H., Ohmura, T., Hasegawa, M., Hirota, S., Makino, M. and Kamiya, M. (1993) Synthesis of galactose derivatives that render lectin-induced agglutinating ability to liposomes. J. Pharm. Sci. 82, 273-275.