Physicochemical characteristics of triacyl lipid A partial structure OM- 174 in relation to biological activity

European Journal of Biochemistry

Volumn 267, Issue 11, 2000, Pages 3370-3377

  Brandenburg, Klaus ^a   Lindner, Buko ^a   Schromm, Andra ^a   Koch, Michel H J ^b   Bauer, Jacques ^c   Merkli, Alain ^c   Zbaeren, Claude ^c   Davies, J Gwynfor ^c,d   Seydel, Ulrich ^a  

^a RESEARCH CENTER BORSTEL   (Germany)

^b EUROPEAN MOLECULAR BIOLOGY LABORATORY   (Germany)

^c Vifor (International) Inc   (Switzerland)

^d ST GEORGE'S UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Endotoxin; Fourier transform infrared (FT IR) spectroscopy; Interleukin (IL) 6; Micellar structure; Phase transition

Indexed keywords

ENDOTOXIN; INTERLEUKIN 6; LIPID A DERIVATIVE; NITRIC OXIDE; OM 174; UNCLASSIFIED DRUG; WATER;

ANIMAL CELL; ARTICLE; CELL MEMBRANE; CHEMICAL STRUCTURE; CONFORMATION; CYTOKINE PRODUCTION; HUMAN; HUMAN CELL; HYDRATION; INFRARED SPECTROSCOPY; LIMULUS LYSATE TEST; LIPID ANALYSIS; MACROPHAGE; MICELLE; MONOCYTE; NONHUMAN; PHASE TRANSITION; PHOSPHOLIPID MEMBRANE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANIMALS; CHEMISTRY, PHYSICAL; CRYSTALLIZATION; GELS; HUMANS; INTERLEUKIN-6; LIMULUS TEST; LIPID A; LIPOSOMES; MACROPHAGES; MEMBRANE FLUIDITY; MEMBRANE LIPIDS; MICE; MICELLES; MOLECULAR STRUCTURE; MONOCYTES; NITRIC OXIDE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STRUCTURE-ACTIVITY RELATIONSHIP; TEMPERATURE;

EID: 0034129209     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1327.2000.01370.x     Document Type: Article

References (37)

1. 1. Rietschel, E.T., Brade, H., Holst, O., Brade, L., Müller-Loennies, S., Mamat, U., Zähringer, U., Beckmann, F., Seydel, U., Brandenburg, K., Ulmer, A.J., Mattern, T., Heine, H., Schletter, J., Hauschildt, S., Loppnow, H., Schönbeck, U., Flad, H.-D., Schade, U.F., Di Padova, F., Kusumoto, S. & Schumann, R.R. (1996) Bacterial endotoxin: chemical constitution, biological recognition, host response, and immunological detoxification. Curr. Top. Microbiol. Immunol. 216, 39-81.
2. 2. Seydel, U., Ulmer, A.J., Uhlig, S. & Rietschel, E.T. (1999) Lipopolysaccharide, a membrane-forming and inflammation-inducing macromolecule. In Membrane Structure in Disease and Drug Therapy (Zimmer, G., ed). Marcel Dekker Inc., New York.
3. 3. Loppnow, H., Flad, H.-D., Rietschel, E.T. & Brade, H. (1993) The active principle of bacterial lipopolysaccharides (endotoxins) for cytokine induction. In Pathophysiology of Shock, Sepsis, and Organ Failure (Schlag, G. & Redl, H., eds), pp. 405-416. Springer-Verlag, Heidelberg.
4. 4. Brandenburg, K., Koch, M.H.J. & Seydel, U. (1990) Phase diagram of lipid A from Salmonella minnesota and Escherichia coli rough mutant lipopolysaccharide. J. Struct. Biol. 105, 11-21.
5. 11 structures of lipid A from Salmonella enterica serovar Minnesota by X-ray diffraction and freeze-fracture electron microscopy. Chem. Phys. Lipids 91, 53-69.
6. 6. Seydel, U., Wiese, A., Schromm, A.B. & Brandenburg, K. (1999) A biophysical view on the function and activity of endotoxins. In Endotoxin in Health and Disease (Morrison, D., Brade, H., Opal, S. & Vogel, S., eds), pp. 195-220. Marcel Dekker, New York.
7. 7. Onier, N., Hilpert, S., Arnould, L., Saint-Giorgio, V., Davies, J.G., Bauer, J. & Jeannin, J.F. (1999) Cure of colon cancer metastasis in rats with the new lipid A OM 174. Apoptosis of tumor cells and immunization of rats. Clin. Exp. Metastas. 17, 299-306.
8. 8. Onier, N., Hilpert, S., Reveneau, S., Arnould, L., Saint-Giorgio, V., Exbrayat, J.M. & Jeannin, J.F. (1999) Expression of th inducible nitric oxide synthase in tumors in relation with their regression induced by lipid A in rats. Int. J. Cancer 81, 755-759.
9. 9. Schromm, A.B., Brandenburg, K., Loppnow, H., Zähringer, U., Rietschel, E.T., Carroll, S.F., Koch, M.H.J., Kusumoto, S. & Seydel, U. (1998) The charge of endotoxin molecules influences their conformation and interleukin-6 inducing capacity. J. Immunol. 161, 5464-5471.
10. 10. Mantsch, H.H. & McElhaney, R.N. (1991) Phospholipid phase transitions in model and biological membranes as studied by infrared spectroscopy. Chem. Phys. Lipids 57, 213-226.
11. 11. Brandenburg, K., Funari, S.S., Koch, M.H.J. & Seydel, U. (1997) Investigation into the acyl chain packing of endotoxins and phospholipids under near physiological conditions by WAXS and FTIR spectroscopy. J. Struct. Biol. 128, 175-186.
12. 12. Koch, M.H.J. & Bordas, J. (1983) X-ray diffraction and scattering on disordered systems using synchrotron radiation. Nucleic Instr. Methods 208, 461-469.
13. 13. Gabriel, A. (1977) Position-sensitive X-ray detector. Rev. Sci. Instrum. 48, 1303-1305.
14. 14. Luzzati, V., Gulik, A., Gulik-Krzywicki, T. & Tardieu, A. (1986) Lipid polymorphism revisited: structural aspects and biological implications. In Lipids and Membranes: Past, Present, and Future (Op den Kamp, J.A.F., Roelofson, B. & Wirtz, K.W.A., eds), pp. 137-151. Elsevier, Amsterdam.
15. 15. Blume, A. (1979) A comparative study of the phase transition of phospholipid bilayers and monolayers. Biochim. Biophys. Acta 557, 32-44.
16. 16. Schromm, A.B., Brandenburg, K., Rietschel, E.T., Flad, H.-D., Carroll, S.F. & Seydel, U. (1996) Lipopolysaccharide binding protein (LBP) mediates CD14-independent intercalation of lipopolysaccharide into phospholipid membranes. FEBS Lett. 399, 267-271.
17. 17. Friberger, P., Sörskog, L., Nilsson, K. & Knös, M. (1987) The use of a quantitative assay in endotoxin testing. In Detection of Bacterial Endotoxin with the Limulus Amebocyte Lysate Test (Watson, S.W., Levin, J. & Novitzky, T.J., eds), pp. 149-169. A. Liss, New York.
18. 18. Brandenburg, K., Kusumoto, S. & Seydel, U. (1997) Conformational studies of synthetic lipid A analogues and partial structures by infrared spectroscopy. Biochim. Biophys. Acta 1329, 193-201.
19. 19. Fringeli, U.P. & Günthard, H.H. (1981) Infrared membrane spectroscopy. In Membrane Spectroscopy (Grell, E., ed.), pp. 270-332. Springer-Verlag, Berlin.
20. 20. Israelachvili, J.N. (1991) Intermolecular and Surface Forces, pp. 213-259. Academic Press, London.
21. A in aqueous solutions at physiological pH. 1: Simple buffer solutions. Chem. Phys. Lipids 59, 167-181.
22. 22. Seydel, U. & Brandenburg, K. (1992) Supramolecular structure of lipopolysaccharides and lipid A. In Bacterial Endotoxic Lipopolysaccharides (Morrison, D.C. & Ryan, J., eds), pp. 225-250. CRC Press, Boca Raton, FL.
23. 23. Seydel, U., Labischinski, H., Kastowsky, M. & Brandenburg, K. (1993) Phase behaviour, supramolecular structure, and molecular conformation of lipopolysaccharide. Immunobiology 187, 191-211.
24. 24. Seydel, U., Brandenburg, K. & Rietschel, E.T. (1994) A case for an endotoxic conformation. Prog. Clin. Biol. Res. 388, 17-30.
25. 25. Brandenburg, K., Mayer, H., Koch, M.H.J., Weckesser, J., Rietschel, E.T. & Seydel, U. (1993) Influence of the supramolecular structure of free lipid A on its biological activity. Eur. J. Biochem. 218, 555-563
26. 26. Shnyra, A., Hultenby, K. & Lindberg, A.A. (1993) Role of the physical state of Salmonella lipopolysaccharide in expression of biological and endotoxic properties. Infect. Immun. 61, 5351-5360.
27. 27. Velucchi, M., Rustici, A. & Porro, M. (1994) Molecular requirements of peptide structures binding the lipid A-region of bacterial endotoxins. In Vaccines 94 (Brown, F., ed.), pp. 141-146. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York.
28. 28. Takayama, K., Zafeer, Z.D. & Mukerjee, P. (1995) Physical state of biologically active lipopolysaccharide. In Bacterial Endotoxins: Lipopolysaccharides from Genes to Therapy (Levin, J., Alving, C.R., Munford, R.S. & Redl, H., eds), pp. 183-193. Wiley-Liss, New-York.
29. 29. Takayama, K., Mitchell, D.H., Din, Z.Z., Mukerjee, P., Li, C. & Coleman, D.L. (1994) Monomeric Re lipopolysaccharide from Escherichia coli is more active than the aggregated form in the Limulus amebocyte lysate assay and in inducing Egr-1 mRNA in murine peritoneal macrophages. J. Biol. Chem. 269, 2241-2244.
30. 30. Wright, S.D., Ramos, R.A., Tobias, P.S., Ulevitch, R.J. & Mathison, J.C. (1990) CD 14, a receptor for complexes of lipopolysaccharide (LPS) and LPS binding protein. Science 249, 1431-1433.
31. 31. Tobias, P.S. & Ulevitch, R.J. (1993) Lipopolysaccharide binding protein and CD14 in LPS dependent macrophage activation. Immunobiology 187, 227-232.
32. 32. Mathison, J., Wolfson, E., Steinemann, S., Tobias, P. & Ulevitch, R. (1993) Lipopolysaccharide (LPS) recognition in macrophages. Participation of LPS-binding protein and CD14 in LPS-induced adaptation in rabbit peritoneal exudate macrophages. J. Clin. Invest. 92, 2053-2059.
33. 33. Kirkland, T.N., Finley, F., Leturcq, D., Moriarty, A., Lee, J.-D., Ulevitch, R.J. & Tobias, P.S. (1993) Analysis of lipopolysaccharide binding by CD14. J. Biol. Chem. 268, 24818-24823.
34. 34. Rietschel, E.T., Kirikae, T., Schade, F.U., Mamat, U., Schmidt, G., Loppnow, H., Ulmer, A.J., Zähringer, U., Seydel, U., Di Padova, F., Schreier, M. & Brade, H. (1994) Bacterial endotoxin: molecular relationships of structure to activity and function. FASEB J. 8, 217-255.
35. 35. Asai, Y., Iwamoto, K. & Watanabe, S. (1998) The effect of the lipid A analog E5531 on phospholipid membrane properties. FEBS Lett. 438, 15-20.
36. 36. Funatogawa, K., Matsuura, M., Nakano, M., Kiso, M. & Hasegawa, A. (1998) Relationship of structure and biological activity of monosaccharide lipid A analogues to induction of nitric oxide production by murine macrophage RAW264.7 cells. Infect. Immun 66, 5792-5798.
37. 37. Takada, H. & Kotani, S. (1989) Structural requirements of lipid A for endotoxicity and other biological activities. CRC Crit. Rev. Microbiol. 16, 477-523.