Endotoxins: Relationship between structure, function, and activity

Sub-Cellular Biochemistry

Volumn 53, Issue , 2010, Pages 53-67

  Brandenburg, K ^a   Schromm, A B ^a   Gutsmann, T ^a  

^a RESEARCH CENTER BORSTEL   (Germany)

Author keywords

Biophysical analysis; FTIR spectroscopy; Lipopolysaccharide; Molecular conformation; Small angle X ray scattering

Indexed keywords

BACTERIA (MICROORGANISMS); NEGIBACTERIA;

ENDOTOXIN;

CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; METABOLISM; PARTICLE SIZE; PROTEIN CONFORMATION; REVIEW; STRUCTURE ACTIVITY RELATION;

ENDOTOXINS; HUMANS; MOLECULAR STRUCTURE; PARTICLE SIZE; PROTEIN CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77956628474     PISSN: 03060225     EISSN: None     Source Type: Journal    
DOI: 10.1007/978-90-481-9078-2_3     Document Type: Article

References (64)

1. Andrá, J., Howe, J., Garidel, P., Rössle, M., Richter, W., Leiva-Leon, J., Moriyon, I., Bartels, R., Gutsmann, T., Brandenburg, K. Mechanism of interaction of optimized Limulus-derived cyclic peptides with endotoxins: thermodynamic, biophysical and microbiological analysis. Biochem J 406 (2007) 297-307.
2. Aurell, C.A., Hawley, M.E., Wistrom, A.O. Direct visualization of Gram-negative bacterial lipopolysaccharide self-assembly. Mol Cell Biol Res Commun 2 (1999) 42-46.
3. Aurell, C.A., Wistrom, A.O., Critical aggregation concentrations of Gram-negative bacterial lipopolysaccharides (LPS). Biochem Biophys Res Commun 253 (1998) 119-123.
4. Blunck, R., Scheel, O., Müller, M., Brandenburg, K., Seitzer, U., Seydel, U., New insights into endotoxin-induced activation of macrophages: Involvement of a K+ channel in transmembrane signaling. J Immunol 166 (2001) 1009-1015.
5. Brandenburg, K. Fourier transform infrared spectroscopy characterization of the lamellar and non-lamellar structures of free lipid A and Re lipopolysaccharides from Salmonella minnesota and Escherichia coli. Biophys J 64 (1993) 1215-1231.
6. Brandenburg, K., Andrá, J., Müller, M., Koch, M.H.J., Garidel, P. Physicochemical properties of bacterial glycopolymers in relation to bioactivity. Carbohydr Res 338 (2003) 2477-2489.
7. Brandenburg, K., Blume, A. Investigations into the thermotropic phase behaviour of natural membranes extracted from Gram-negative bacteria and artificial membrane systems made from lipopolysaccharides and free lipid A. Thermochim Acta 119 (1987) 127-142.
8. Brandenburg, K., Hawkins, L., Garidel, P., Andrá, J., Müller, M., Heine, H., Koch, M.H.J., Seydel, U. Structural polymorphism and endotoxic activity of synthetic phospholipid-like amphiphiles. Biochemistry 43 (2004) 4039-4046.
9. Brandenburg, K., Koch, M.H.J., Seydel, U. Phase diagram of lipid A from Salmonella minnesota and Escherichia coli rough mutant lipopolysaccharide. J Struct Biol 105 (1990) 11-21.
10. Brandenburg, K., Seydel, U. Investigation into the fluidity of lipopolysaccharide and free lipid A membrane systems by Fourier-transform infrared spectroscopy and differential scanning calorimetry. Eur J. Biochem 191 (1990) 229-236.
11. Brandenburg, K., Koch, M.H.J., Seydel, U. Phase diagramm of deep rough mutant lipopolysaccharide from Salmonella minnesota R595. J Struct Biol 108 (1992) 93-106.
12. Brandenburg, K., Kusumoto, S., Seydel U. Conformational studies of synthetic lipid A analogues and partial structures by infrared spectroscopy. Biochim Biophys Acta 1329 (1997) 193-201.
13. Brandenburg, K., Matsuura, M., Heine, H., Müller, M., Kiso, M., Ishida, H., Koch, M.H.J., Seydel, U. Biophysical characterization of triacyl monosaccharide lipid A partial structures in relation to bioactivity. Biophys J 83 (2002) 322-333.
14. Brandenburg, K., Mayer, H., Koch, M.H.J., Weckesser, J., Rietschel, E.Th., Seydel, U. Influence of the supramolecular structure of free lipid A on its biological activity. Eur J Biochem 218 (1993) 555-563.
15. Brandenburg, K., Seydel, U. Physical aspects of structure and function of membranes made from lipopolysaccharides and free lipid A. Biochim Biophys Acta 775 (1984) 225-238.
16. Brandenburg, K., Seydel, U. Infrared spectroscopy of glycolipids. Chem Phys Lipids 96 (1998) 23-40.
17. Brandenburg, K., Wagner, F., Müller, M., Heine, H., Andrá, J., Koch, M.H.J., Záhringer, U., Seydel, U. Physicochemical characterization and biological activity of a glycoglycerolipid from Mycoplasma fermentans. Eur J Biochem 270 (2003) 3271-3279.
18. Chen, X., Howe, J., Andra, J., Rossle, M., Richter, W., da Silva, A.P., Krensky, A.M., Clayberger, C., Brandenburg, K. Biophysical analysis of the interaction of granulysin-derived peptides with enterobacterial endotoxins. Biochim Biophys Acta 1768 (2007) 2421-2431.
19. Garidel, P., Rappolt, M., Schromm, A.B., Howe, J., Lohner, K., Andrá, J., Koch, M.H., Brandenburg, K. Divalent cations affect chain mobility and aggregate structure of lipopolysaccharide from Salmonella minnesota reflected in a decrease of its biological activity, Biochim Biophys Acta 1715 (2005) 122-131.
20. Gioannini, T.L., Teghanemt, A., Zhang, D., Coussens, N.P., Dockstader, W., Ramaswamy, S., Weiss, J.P. Isolation of an endotoxin-MD-2 complex that produces Toll-like receptor 4-dependent cell activation at picomolar concentrations. Proc Natl Acad Sci USA 101 (2004) 4186-4191.
21. Gutsmann, T., Haberer, N., Carroll, S.F., Seydel, U., Wiese, A. Interaction between lipopolysac-charide (LPS), LPS-binding protein (LBP), and planar membranes, Biol Chem 382 (2001a) 425-434.
22. Gutsmann, T., Mueller, M., Carroll, S.F., MacKenzie, R.C., Wiese, A., Seydel, U. Dual role of lipopolysaccharide (LPS)-binding protein in neutralization of LPS and enhancement of LPS-induced activation of mononuclear cells. Infect Immun 69 (2001b) 6942-6950.
23. Gutsmann, T., Schromm, A.B., Koch, M.H.J., Kusumoto, S., Fukase, K., Oikawa, M., Seydel, U., Brandenburg, K. Lipopolysaccharide-binding protein-mediated interaction of lipid A from different origin with phospholipid membranes. Phys Chem Chem Phys 2 (2000) 4521-4528.
24. Holst, O. Chemical structure of the core region of lipopolysaccharides. In Brade, H., Opal, S.M., Vogel, S.N., Morrison, D.C. (eds), Endotoxin in Health and Disease, Marcel Dekker, Inc., New York, NY (1999), pp. 115-154.
25. Holst, O., Ulmer, A.J., Brade, H., Flad, H.D., Rietschel, E.T. Biochemistry and cell biology of bacterial endotoxins. FEMS Immunol Med Microbiol 16 (1996) 83-104.
26. Howe, J., Hammer, M., Alexander, C., Rossle, M., Fournier, K., Mach, J.P., Waelli, T., Gorczynski, R.M., Ulmer, A.J., Zahringer, U., Rietschel, E.T., Brandenburg, K. Biophysicalcharacterization of the interaction of endotoxins with hemoglobins. Med Chem 3 (2007) 13-20. 66
27. K. Brandenburg et al. Israelachvili, J.N., Intermolecular and surface forces. In Israelachvili, J.N. (ed), Academic, London (1991), pp. 366-394.
28. Jiao, B., Freudenberg, M., Galanos, C. Characterization of the lipid A component of genuine smooth-form lipopolysaccharide. Eur J Biochem 180 (1989) 515-518.
29. Kastowsky, M., Gutberlet, T., Bradaczek, H. Comparison of X-ray powder-diffraction data of various bacterial lipopolysaccharide structures with theoretical model conformations. Eur J Biochem 217 (1993) 771-779.
30. Kastowsky, M., Sabisch, A., Gutberlet, T., Bradaczek, H. Molecular modelling of bacterial deep rough mutant lipopolysaccharide of Escherichia coli, Eur J Biochem 197 (1991) 707-716.
31. Kitchens, R.L., Munford, R.S. CD14-dependent internalization of bacterial lipopolysaccharide (LPS) is strongly influenced by LPS aggregation but not by cellular responses to LPS. J Immunol 160 (1998) 1920-1928.
32. Loppnow, H., Flad, H.-D., Rietschel, E.Th., Brade, H. The active principle of bacterial lipopolysac-charides (endotoxins) for cytokine induction. In Schlag, G., Redl, H.(eds), Pathophysiology of Shock, Sepsis, and Organ. Springer-Verlag, Heidelberg (1993), pp. 405-416.
33. Loppnow, H., Libby, P., Freudenberg, M.A., Kraus, J.H., Weckesser, J., Mayer, H. Cytokine induction by lipopolysaccharide (LPS) corresponds to the lethal toxicity and is inhibited by nontoxic Rhodobacter capsulatus LPS. Infect Immun 58 (1990) 3743-3750.
34. Luzzati, V., Gulik, A., Gulik-Krzywicki, T., Tardieu, A. Lipid polymorphism revisited: Structural aspects and biological implications. Lipids and Membranes: Past, Present, and Future. Elsevier, Amsterdam (1986), pp. 137-151.
35. Maurer, N., Glatter, O., Hofer, M. Determination of size and structure of lipid IV a vesicles by quasi-elastic light scattering and small-angle X-ray scattering. J Appl Cryst 24 (1991) 832-835.
36. Mayer, H., Weckesser, J. 'Unusual' lipid A's: structures, taxonomical relevance and potential value for endotoxin research. In Rietschel, E.T. (ed), Handbook of Endotoxin, Vol.1: Chemistry of Endotoxin. Elsevier, Amsterdam (1984), p. 221.
37. Mueller, M., Brandenburg, K., Dedrick, R., Schromm, A.B., Seydel, U. Phospholipids inhibit lipopolysaccharide (LPS)-induced cell activation: a role for LPS-binding protein. J Immunol 174 (2005a) 1091-1096.
38. Mueller, M., Lindner, B., Dedrick, R., Schromm, A.B., Seydel, U. Endotoxin: physical requirements for cell activation. J Endotoxin Res 11 (2005b) 299-303.
39. Mueller, M., Lindner, B., Kusumoto, S., Fukase, K., Schromm, A.B., Seydel, U. Aggregates are the biologically active units of endotoxin. J Biol Chem 279 (2004) 26307-26313.
40. Naumann, D., Schultz, C., Sabisch, A., Kastowsky, M., Labischinski, H. New insights into the phase behaviour of a complex anionic amphiphile: Architecture and dynamics of bacterial deep rough mutant lipopolysaccharide membranes as seen by FTIR, X-ray, and molecular modelling techniques. J Molec Struct 214 (1989) 213-246.
41. Nomura, K., Inaba, T., Morigaki, K., Brandenburg, K., Seydel, U., Kusumoto, S. Interaction of lipopolysaccharide and phospholipid in mixed membranes: solid-state 31P-NMR spectroscopic and microscopic investigations. Biophys J 95 (2008) 1226-1238.
42. Reichelt, H., Faunce, C.A., Paradies, H.H. The phase diagram of charged colloidal lipid A-diphosphate dispersions. J Phys Chem B 112 (2008) 3290-3293.
43. Rietschel, E.Th., Brade, L., Schade, U., Seydel, U., Záhringer, U., Brandenburg, K., Helander, I., Holst, O., Kondo, S., Kuhn, H.M., Lindner, B., Röhrscheidt, E., Russa, R., Labischinski, H., Naumann, D., Brade, H. Bacterial Lipopolysaccharides: Relationship of Structure and Conformation to Endotoxic Activity, Seriological Specificity and Biological Function. In Friedmann, H., Klien, T.W., Nakano, M., Nowotny, A. (eds) Endotoxin, Plenum. New York, NY (1990), pp. 81-99.
44. Rietschel, E.Th., Galanos, C., Tanaka, A., Ruschmann, E., Lüderitz, O., Westphal O. Biological activities of chemically modified endotoxins. Eur J Biochem 22 (1971) 218-224.
45. Rietschel, E.Th., Seydel, U., Záhringer, U., Schade, U.F., Brade, L., Loppnow, H., Feist, W., Wang, M.-H., Ulmer, A.J., Flad, H.-D., Brandenburg, K., Kirikae, T., Grimmecke, D., Holst, O., Brade, H. Bacterial endotoxin: Molecular relationships between structure and activity. Infect Dis Clin North Am 5 (1991) 753-779.
46. Risco, C., Carrascosa, J.L., Bosch, M.A. Visualization of lipopolysaccharide aggregates by freezefracture and negative staining. J Electron Microsc 42 (1993) 202-204.
47. Sasaki, H., White, S.H. Aggregation behavior of an ultra-pure lipopolysaccharide that stimulates TLR-4 receptors. Biophys J 95 (2008) 986-993.
48. Schromm, A.B., Brandenburg, K., Rietschel, E.T., Flad, H.D., Carroll, S.F., Seydel, U., Schromm, A.B. Lipopolysaccharide-binding protein mediates CD14-independent intercalation of lipopolysaccharide into phospholipid membranes. FEBS Lett 399 (1996) 267-271.
49. Schromm, A.B., Howe, J., Ulmer, A.J., Wiesmüller, K.H., Seyberth, T., Jung, G., Rössle, M., Koch, M.H., Gutsmann, T., Brandenburg, K. Physicochemical and biological analysis of synthetic bacterial lipopeptides: validity of the concept of endotoxic conformation. J Biol Chem 282 (2007) 11030-11037.
50. Schromm, A.B., Brandenburg, K., Loppnow, H., Moran, A.P., Koch, M.H.J., Rietschel, E.Th., Seydel, U. Biological activities of lipopolysaccharides are determined by the shape of their lipid A portion. Eur J Biochem 267 (2000) 2008-2013.
51. Schromm, A.B., Brandenburg, K., Loppnow, H., Záhringer, U., Rietschel, E.Th., Carroll, S.F., Koch, M.H.J., Kusumoto, S., Seydel, U., The charge of endotoxin molecules influences their conformation and interleukin-6 inducing capacity. J Immunol 161 (1998) 5464-5471.
52. Schromm, A.B., Reiling, N., Howe, J., Wiesmuller, K.H., Roessle, M., Brandenburg, K. Influence of serum on the immune recognition of a synthetic lipopeptide mimetic of the 19-kDa lipoprotein from Mycobacterium tuberculosis. Innate Immun (2010) (in press).
53. Seydel, U., Hawkins, L., Schromm, A.B., Heine, H., Scheel, O., Koch, M.H., Brandenburg, K. The generalized endotoxic principle. Eur J Immunol 33 (2003) 1586-1592.
54. Seydel, U., Koch, M.H.J., Brandenburg, K. Structural polymorphisms of rough mutant lipopolysac-charides Rd to Ra from Salmonella minnesota. J Struct Biol 110 (1993) 232-243.
55. Seydel, U., Oikawa, M., Fukase, K., Kusumoto, S., Brandenburg, K. Intrinsic conformation oflipid A is responsible for agonistic and antagonistic activity. Eur J Biochem 267 (2000) 3032-3039.
56. Seydel, U., Schromm, A.B., Brade, L., Gronow, S., Andrá, J., Müller, M., Koch, M.H., Fukase, K., Kataoka, M., Hashimoto, M., Kusumoto, S., Brandenburg, K. Physicochemical characterization of carboxymethyl lipid A derivatives in relation to biological activity. FEBS J 272 (2005) 327340.
57. Seydel, U., Ulmer, A.J., Uhlig, S., Rietschel, E.Th. Lipopolysaccharide, a membrane-forming and inflammation-inducing bacterial macromolecule. In Zimmer, G. (ed), Membrane Structure in Disease and Drug Therapy. Marcel Dekker Inc, New York, NY (1999), pp. 217-252.
58. Shands, J.W. The physical structure of bacterial lipopolysaccharides. In Weinbaum, G., Kadis, S., Ajl, S.J. (eds), Microbial Toxins, Vol. 4: Bacterial Endotoxins. Academic, New York, NY (1971), pp. 127-144.
59. Shnyra, A., Hultenby, K., Lindberg, A.A., Role of the physical state of Salmonella lipopolysaccharide in expression of biological and endotoxic properties. Infect Immun 61 (1993) 5351-5360.
60. Takayama, K., Din, Z.Z., Mukerjee, P., Cooke, P.H., Kirkland, T.N. Physicochemical properties of the lipopolysaccharide unit that activates B lymphocytes. J Biol Chem 265 (1990) 14023-14029.
61. Teghanemt, A., Prohinar, P., Gioannini, T.L., Weiss, J.P. Transfer of monomeric endotoxin from MD-2 to CD14: characterization and functional consequences. J Biol Chem 282 (2007) 36250-36256.
62. Tobias, P.S., Soldau, K., Iovine, N.M., Elsbach, P., Weiss, J. Lipopolysaccharide (LPS)-binding proteins BPI and LBP form different types of complexes with LPS. J Biol Chem 272 (1997) 18682-18685.
63. Toman, R., Garidel, P., Andrá, J., Slaba, K., Hussein, A., Koch, M.H.J., Brandenburg, K. Physicochemical characterization of the endotoxins from Coxiella burnetii strain Priscilla in relation to their bioactivities. BMC Biochem 5 (2004) 1.
64. Záhringer, U., Salvetzki, R., Ulmer, A.J., Rietschel, E.Th., Isolation, chemical analysis and biological investigations of natural lipid A and lipid A-antagonists. J Endotoxin Res 3 (Suppl. 1) (1996) 33.