Analysis of Quil A-phospholipid mixtures using drift spectroscopy

International Journal of Pharmaceutics

Volumn 342, Issue 1-2, 2007, Pages 49-61

  Demana, Patrick H ^a   Davies, Nigel M ^b   Hook, Sarah ^c   Rades, Thomas ^c  

^a TSHWANE UNIVERSITY OF TECHNOLOGY   (South Africa)

^b UNIVERSITY OF QUEENSLAND   (Australia)

^c UNIVERSITY OF OTAGO   (New Zealand)

Author keywords

Cholesterol; Infra red spectroscopy; Phosphatidylcholine; Quil A

Indexed keywords

CHOLINE; GLUCURONIC ACID; PHOSPHATE; PHOSPHATIDYLCHOLINE; PHOSPHOLIPID; QUIL A;

ARTICLE; FOURIER TRANSFORM MASS SPECTROMETRY; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR INTERACTION; PRIORITY JOURNAL; SOLID STATE; SPECTROSCOPY;

ADJUVANTS, IMMUNOLOGIC; CARBOHYDRATE SEQUENCE; CHOLESTEROL; CHOLINE; FATTY ACIDS; FREEZE DRYING; MOLECULAR SEQUENCE DATA; PHOSPHATES; PHOSPHATIDYLCHOLINES; PHOSPHOLIPIDS; POWDERS; SAPONINS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 34547892258     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2007.04.030     Document Type: Article

References (79)

1. Akutsu H. Direct determination by Raman scattering of the conformation of the choline group in phospholipid bilayers. Biochemistry 20 (1981) 7359-7366
2. Arrondo J.L.R., and Goni F.M. Infrared studies of protein-induced perturbations of lipids in lipoproteins and membranes. Chem. Phys. Lipids 96 (1998) 53-68
3. Barr I.G., and Mitchell G.F. ISCOMs (immunostimulating complexes): the first decade. Immunol. Cell. Biol. 74 (1996) 8-25
4. Barr I.G., Sjölander A., and Cox J.C. ISCOMs and other saponin based adjuvants. Adv. Drug. Deliv. Rev. 32 (1998) 247-271
5. Berbenni V., Marini A., Bruni G., and Cardini A. Thermoanalytical and spectroscopic characterisation of solid-state retinoic acid. Int. J. Pharm. 221 (2001) 123-141
6. 13C{double bond, long}O-labelled phospholipids. Hydrogen bonding to carbonyl groups. Biochemistry 27 (1988) 8239-8249
7. Brandenburg K., and Seydel U. Infrared spectroscopy of glycolipids. Chem. Phys. Lipids 96 (1998) 23-40
8. Brandenburg K., Funari S.S., Koch M.H.J., and Seydel U. Investigation into the acyl chain packing of endotoxins and phospholipids under near physiological conditions by WAXS and FTIR spectroscopy. J. Struct. Biol. 128 (1999) 175-186
9. Bush S.F., Levin H., and Levin I.W. Cholesterol-lipid interactions: an infra-red and Raman spectroscopic study of the carbonyl stretching mode region of 1,2-dipalmitoyl phosphatidylcholine bilayers. Chem. Phys. Lipids 27 (1980) 101-111
10. Cacela C., and Hincha D.K. Monosaccharide composition, chain length and linkage type influence the interactions of oligosaccharides with dry phosphatidylcholine membranes. Biochim. Biophys. Acta 1758 (2006) 680-691
11. Cameron D.G., Casal H.L., and Mantsch H.H. Characterisation of the pretransition in 1,2-dipalmitoyl-sn-glycero-3-phosphocholine by Fourier transform infrared spectroscopy. Biochemistry 19 (1980) 3665-3672
12. Cannon B., Heath G., Huang J., Somerharju P., and Virtanen J.A. Time-resolved fluorescence and Fourier transform infrared spectroscopic investigations of lateral packing defects and superlattice domains in compositionally uniform cholesterol/phosphatidylcholine bilayers. Biophys. J. 84 (2003) 3777-3791
13. Casal H.L., Cameron D.G., Smith I.C.P., and Mantsch H.H. Acholeplasma laidlawii membranes: A Fourier transform infrared study of the influence of protein on lipid organisation and dynamics. Biochemistry 19 (1980) 444-451
14. 2+ with phosphatidylserines: effect of hydrocarbon chain unsaturation. Biochim. Biophys. Acta 982 (1989) 228-236
15. Castano S., and Desbat B. Structure and orientation of fusion peptide FP23 of gp41 from HIV-1 alone or inserted into various lipid membrane models (mono-, bi- and multibilayers) by FTIR spectroscopies and Brewster angle microscopy. Biochim. Biophys. Acta 1715 (2005) 81-95
16. Crowe L.M. Lessons from nature: the role of sugars in anhydrobiosis. Comp. Biochem. Physiol. 131 (2002) 505-513
17. Crowe J.H., Crowe L.M., Carpenter J.F., Rudolph A.S., Aurell-Wistrom C., Spargo B.J., and Anchordoguy T.J. Interaction of sugars with membranes. Biochim. Biophys. Acta 947 (1988) 367-384
18. Daghbouche Y., Garrigues S., and de la Guardia M. Liquid chromatography-Fourier transform infrared spectrometric determination of cholesterol in animal greases. Anal. Chim. Acta 354 (1997) 97-106
19. Dalsgaard K. Saponin adjuvants III. Isolation of a substance from Quillaja saponaria Molina with adjuvant activity in foot-and-mouth disease vaccines. Archiv fuer die gesamte Virusforschung 44 (1974) 243-254
20. Demana P.H., Fehske C., White K., Rades T., and Hook S. Effect of incorporation of the adjuvant Quil A on structure and immune stimulatory capacity of liposomes. Immunol. Cell. Biol. 82 (2004) 547-554
21. Demana P.H., Davies N.M., Vosgerau U., and Rades T. Pseudo-ternary phase diagrams of aqueous mixtures of Quil A, cholesterol and phospholipid prepared by the lipid-film hydration method. Int. J. Pharm. 270 (2004) 229-239
22. Demana P.H., Davies N.M., Berger B., Vosgerau U., and Rades T. A comparison of pseudo-ternary diagrams of aqueous mixtures of Quil A, cholesterol and phospholipid prepared by the lipid- film hydration and dialysis. J. Pharm. Pharmacol. 56 (2004) 573-580
23. Demana P.H., Davies N.M., Hook S., and Rades T. Quil A-lipid powder formulations releasing ISCOMs and colloidal structures upon hydration. J. Contr. Rel. 103 (2005) 45-59
24. Dijiba Y.K., Zhang A., and Niemczyk T.M. Determinations of ephedrine in mixtures of ephedrine and pseudoephedrine using diffuse reflectance infrared spectroscopy. Int. J. Pharm. 289 (2005) 39-49
25. El-Aneed A. An overview of current delivery systems in cancer gene therapy. J. Contr. Rel. 94 (2004) 1-14
26. Faiman R. Raman spectroscopic studies of different forms of cholesterol and its derivatives in the crystalline state. Chem. Phys. Lipids 18 (1977) 84-104
27. Glauert A.M., Dingle J.T., and Lucy J.A. Action of saponin on biological cell membranes. Nature 196 (1962) 953-955
28. Grdadolnik J., Kidric J., and Hadzi D. Hydration of phosphatidylcholine reverse micelles and multilayers-an infrared spectroscopic study. Chem. Phys. Lipids 59 (1991) 57-68
29. Grdadolnik J., and Hadzi D. Conformational effects of metal salt binding to the polar head of phosphatidylcholines investigated by FTIR spectroscopy. Chem. Phys. Lipids 65 (1993) 121-132
30. Hattab N.E., Daghbouche Y., Hattab M.E., Piovetti L., Garrigues S., and de la Guardia M. FTIR-determination of sterols from the red alga Asparagopsis armata: comparative studies with HPLC. Talanta 68 (2006) 1230-1235
31. Higuchi R., and Komori T. Structures of compounds derived from the acyl moieties of Quillaja saponin. Phytochemistry 26 (1987) 2357-2360
32. Hincha D.K., and Crowe J.H. The lytic activity of the bee venom peptide mellitin is strongly reduced by the presence of negatively charged phospholipids chloroplast galactolipids in the membranes of phosphatidylcholine large unilamellar vesicles. Biochim. Biophys. Acta 1284 (1996) 162-170
33. Höglund S., Dalsgaard K., Lövgren K., Sundquist B., Osterhaus A., and Morein B. ISCOMs and immunostimulation with viral antigens. In: Harris J.R. (Ed). Subcellular Biochemistry. 1st ed. (1989), Plenum, New York 39-68
34. Horzinek M., and Mussgay M. Studies on the substructure of Togaviruses. I. Effect of urea, deoxycholate, and saponin on the Sindbis virion. Archiv fuer die gesamte Virusforschung 33 (1971) 296-305
35. Hübner W., and Blume A.W. Interactions at the lipid-water interface. Chem. Phys. Lipids 96 (1998) 99-123
36. Kensil C.R., Patel U., Lennick M., and Marciani D. Separation and characterization of saponins with adjuvant activity from Quillaja saponaria Molina cortex. J. Immunol. 146 (1991) 431-437
37. Kensil C.R. Saponins as vaccine adjuvants. Crit. Rev. Ther. Drug Carrier Syst. 13 (1996) 1-55
38. Kersten, G.F.A., 1990. Aspects of ISCOMs. Analytical, pharmaceutical and adjuvant properties. School of Pharmaceutical Sciences, University of Utrecht, PhD Thesis.
39. Kersten, G.F.A., Spiekstra, A., Beuvery, E.C., Crommelin, D.J.A., 1991. On the structure of immune-stimulating saponin-lipid complexes (ISCOMs). Biochim. Biophys. Acta, 1062, 165-171.
40. Kersten G.F.A., and Crommelin D.J.A. Liposomes and ISCOMs. Vaccine 21 (2003) 915-920
41. Kodati V.R., El-Jastimi R., and Lafleur M. Contribution of the intermolecular coupling and librotorsional mobility in the methylene stretching modes in the infrared spectra of acyl chains. J. Phys. Chem. 98 (1994) 12191-12197
42. Laugel, C., Yagoubi, N., Baillet, A., in press. ATR-FTIR spectroscopy: a chemometric approach for studying the lipid organisation of the stratum corneum, Chem. Phys. Lipids, 135, 55-68.
43. Lendemans D.G., Myschik J., Hook S., and Rades T. Immuno-stimulating complexes prepared by ethanol injection. J. Pharm. Pharmacol. 57 (2005) 729-733
44. Lendemans D.G., Myschik J., Hook S., and Rades T. Cationic cage-like complexes formed by DC-cholesterol, Quil A and phospholipid. J. Pharm. Sci. 94 (2005) 1794-1807
45. Lendemans D.G., Egert A.M., Hook S., and Rades T. Cage-like complexes formed by DOTAP, Quil A and cholesterol. Int. J. Pharm. 332 (2007) 192-195
46. Levin I.W. Vibrational spectroscopy of membrane assemblies. Advances in Infrared and Raman Spectroscopy vol. 11 (1984), Wiley Heyden pp. 1-48
47. Lewis R.N.A.H., and McElhaney R.N. The structure and organisation of phospholipid bilayers as revealed by infrared spectroscopy. Chem. Phys. Lipids 96 (1998) 9-21
48. Mantsch H.H., Martin A., and Cameron D.G. Characterization by infrared spectroscopy of the bilayer to non-bilayer phase transition of phosphatidylethanolamines. Biochemistry 20 (1981) 3138-3145
49. Mantsch H.H., and McElhaney R.N. Phospholipid phase transitions in model and biological membranes as studied by infrared spectroscopy. Chem. Phys. Lipids 57 (1991) 213-226
50. Matsuzaki K., Shioyama T., Okamura E., Umemura J., Takenaka T., Takaishi Y., Fujita T., and Miyajima K. A comparative study on interactions of α-aminoisobutyric acid containing antibiotic peptides, trichopolyn I and hypelcin A with phosphatidylcholine bilayers. Biochim. Biophys. Acta 1070 (1991) 419-428
51. McMullen T.P.W., Lewis R.N.A.H., and McElhaney R.N. Differential scanning calorimetric and Fourier transform infrared spectroscopic studies of the effects of cholesterol on the thermotropic phase behaviour and organisation of a homologous series of linear saturated phosphatidylserine bilayer membranes. Biophys. J. 79 (2000) 2056-2065
52. 62 mixtures. Biochim. Biophys. Acta 774 (1984) 237-246
53. Morein B., Sundquist B., Höglund S., Dalsgaard K., and Osterhaus S. ISCOM, a novel structure for antigenic presentation of membrane proteins from enveloped viruses. Nature 308 (1984) 457-460
54. Morein B., and Bengtsson K.L. Immunomodulation by ISCOMs, immunostimulating complexes. Enzymology 19 (1999) 94-102
55. Myschik J., Lendemans D.J., McBurney W.T., Demana P.H., Hook S., and Rades T. On the preparation, microscopic investigation and application of ISCOMs. Micron 37 (2006) 724-734
56. Myschik J., McBurney W.T., Eberhardt F., Hennessy T., Phipps-Green M., Rades T., and Hook S. Quil-A containing lipid implants as potential delivery system for subunit cancer vaccines. N.Z. Med. J 119 (2006) 1237
57. Naumann D., Schultz C., Born J., Labischinski H., Brandenburg K., Von Busse G., Brade G., and Seydel U. Investigations into the polymorphism of lipid A from lipopolysaccharides of Escherichia coli and Salmonella Minnesota by Fourier-transform infrared spectroscopy. Eur. J. Biochem. 164 (1987) 159-169
58. Özel M., Höglund S., Gelderblom H.R., and Morein B. Quaternary structure of the immunostimulating complex (ISCOM). J. Ultrastruct. Mol. Struct. Res. 102 (1989) 240-248 (J. Struct. Biol.)
59. 2H nuclear magnetic resonance and infrared spectroscopic investigation. Biophys. J. 74 (1998) 899-909
60. Pham H.L., Shaw P.N., and Davies N.M. Preparation of immuno-stimulating complexes (ISCOMs) by ether injection. Int. J. Pharm. 310 (2006) 196-202
61. Pohle W., Gauger D.R., Bohl M., Mrazkova E., and Hobza P. Lipid hydration: headgroup CH moieties are involved in water binding. Biopolymers 74 (2004) 27-31
62. Popova A.V., and Hincha D.K. Intermolecular interactions in dry and rehydrated pure and mixed bilayers of phosphatidylcholine and digalactosyldiacylglycerol: a Fourier transform infrared spectroscopy study. Biophys. J. 85 (2003) 1682-1690
63. Popova A.V., and Hincha D.K. Specific interactions of tryptophan with phosphatidylcholine and digalactosyldiacylglycerol in pure and mixed bilayers in the dry and hydrated state. Chem. Phys. Lipids 132 (2004) 171-184
64. Roberts G., Gallagher B.S., and Jones R.N. Infrared Absorption Spectra of Steroids, An Atlas vol. 2 (1958), Interscience Publishers, New York p. 31
65. Ronnberg B., Fekadu M., and Morein B. Adjuvant activity of non-toxic Quillaja saponaria Molina components for use in ISCOM matrix. Vaccine 13 (1995) 1375-1382
66. Ronnberg B., Fekadu M., Behboudi S., Kenne L., and Morein B. Effects of carbohydrate modification of Quillaja saponaria Molina QH-B fraction on adjuvant activity, cholesterol-binding capacity and toxicity. Vaccine 15 (1997) 1820-1826
67. Sailer K., Viaggi S., and Nusse M. Kinetics of radiation- and cytochrome c-induced modifications in liposomes analysed by FT-Raman spectroscopy. Biochim. Biophys. Acta 1329 (1997) 259-268
68. Sanders T.S., Brown L.E., Deliyannis G., Pearse M.J., and Ronnberg. ISCOM-based vaccines: the second decade. Immunol. Cell. Biol. 83 (2005) 119-128
69. Singh M., and O'Hagan D.T. Molecular factors influencing retention on immobilized artificial membranes (IAM) compared to partitioning in liposomes and n-octanol. Pharm. Res. 19 (2002) 715-728
70. Sjölander A., Cox J.C., and Barr I.G. ISCOMs: an adjuvant with multiple functions. J. Leukoc. Biol. 64 (1998) 713-723
71. Sujak A., Gabrielska J., Milanowska J., Mazurek P., Strzalka K., and Gruszecki W.I. Studies on canthaxanthin in lipid membranes. Biochim. Biophys. Acta 1712 (2005) 17-28
72. Tantipolphan R., Rades T., Strachan C.J., Gordon K.C., and Medlicott N.J. Analysis of lecithin-cholesterol mixtures using Raman spectroscopy. J. Pharm. Biomed. Anal. 41 (2006) 476-484
73. Taylor M.O., and Smith I.C.P. The fidelity of response by nitroxide spin probes to changes in membrane organisation: the condensing effect of cholesterol. Biochim. Biophys. Acta 599 (1980) 140-149
74. Umemura J., Cameron D.G., and Mantsch H.H. A Fourier transform infrared spectroscopic study of the molecular interaction of cholesterol with 1,2-dipalmitoyl-sn-glycero-3-phosphocholine. Biochim. Biophys. Acta 602 (1980) 32-44
75. Verma S., and Wallach D.F.H. Effects of cholesterol on the infrared dichroism of phosphatide multibilayers. Biochim. Biophys. Acta 330 (1973) 122-131
76. Vippagunta S.R., Maul K.A., Tallavajhala S., and Grant D.J.W. Solid-state characterisation of nifedipine solid dispersions. Int. J. Pharm. 236 (2002) 111-123
77. Williams R.O., Mahaguna V., and Sriwongjanya M. Characterization of an inclusion complex of cholesterol and hydroxypropyl-β-cyclodextrin. Eur. J. Pharm. Biopharm. 46 (1998) 355-360
78. Wolkers W.F., Oldenhof H., Tablin F., and Crowe J.H. Preservation of dried liposomes in the presence of sugar and phosphate. Biochim. Biophys. Acta 1661 (2004) 125-134
79. Wong P.T.T., Capes S.E., and Mantsch H.H. Hydrogen bonding between anhydrous cholesterol and phosphatidylcholines: an infrared spectroscopic study. Biochim. Biophys. Acta 980 (1989) 37-41