Conformation and supramolecular structure of lipid A

Advances in Experimental Medicine and Biology

Volumn 667, Issue , 2009, Pages 25-38

  Brandenburg, Klaus ^b   Seydel, Ulrich ^a  

^a RESEARCH CENTER BORSTEL   (Germany)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIUM LIPOPOLYSACCHARIDE; HEAT SHOCK PROTEIN 70; HEAT SHOCK PROTEIN 90; LIPID A; LIPID A DERIVATIVE; TOLL LIKE RECEPTOR 4;

ACYLATION; ANTIGEN BINDING; ARTICLE; BACTERIAL STRAIN; BINDING SITE; BIOMEDICINE; CELL AGGREGATION; CHEMICAL STRUCTURE; CONFORMATION; CRYSTALLIZATION; CYTOKINE PRODUCTION; DEPHOSPHORYLATION; ENDOTHELIUM CELL; EQUILIBRIUM DIALYSIS; FLUORESCENCE SPECTROSCOPY; HYDROPHILICITY; HYDROPHOBICITY; INFRARED SPECTROSCOPY; LIPID ANALYSIS; MOLECULAR MODEL; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTEIN AGGREGATION; PROTEIN BINDING;

CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; LIPID A; MODELS, MOLECULAR;

BACTERIA (MICROORGANISMS);

EID: 77952540747     PISSN: 00652598     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-4419-1603-7_3     Document Type: Article

References (70)

1. Rietschel ETh, Galanos C, Tanaka A et al. Biological activities of chemically modified endotoxins. Eur J Biochem 1971; 22:218-224.
2. Rietschel ETh, Kirikae T, Schade FU et al. Bacterial endotoxin: Molecular relationships of structure to activity and function. FASEBJ 1994; 8:217-225. (Pubitemid 24067145)
3. Nikaido H, Vaara M. Molecular basis of bacterial outer membrane permeability. Microbial Rev 1985; 49:1-32. (Pubitemid 15134118)
4. Golenbock DT, Hampton RY, Qureshi N et al. Lipid A-like molecules that antagonize the effects of endotoxins on human monocytes. J Biol Chern 1991; 266:19490-19498. (Pubitemid 21908258)
5. Mayer H, Krauss JH, Yokota A et al. Natural variants of lipid A. In: Friedman H, Klein TW; Nakano M and Nowotny A, eds Endotoxin, New York and London : Plenum press, 1990:45-70.
6. Loppnow H. Rierschel ETh. Brade H et al. Lipid A precursor Ia (compound 406) and Rhodobacrer capsulatus lipopolysaccharide: Potent endotoxin antagonists in the human sysrem in vitro. Levin. J, Alving, CR. Munford. RS et al. P.337-348. 1993. Amsterdam. Elsevier. Bacterial endotoxin: Recognition and effector mechanisms.
7. Hofer M. Hampton RY. Raetz CRH et al. Aggregation behavior of lipid IVA in aqueous solutions at physiological pH 1: Simple buffer solutions. Chem Phys Lipids 1991; 59:167-181.
8. Takayama K. Din ZZ, Mukerjee P et al. Physicochemical properties of the lipopolysaccharide unit that activates B lymphocytes. J Biol Chern 1990; 265:14023-14029.
9. Buschner S. Bestimmung der kritischen Aggregatkonzentrationen von Lipiden: Implikationen fur die biologische Wirksamkeit von Endoroxinen, Universitat Kiel 1999; PhD Thesis.
10. Aurell CA. Wistrom AO. Critical aggregation concentrations of gram-negative bacteriallipopolysaccharides (LPS). Biochem Biophys Res Commun 1998; 253:119-123. (Pubitemid 29015610)
11. Mueller M. Lindner B. Dedrick Ret al. Endotoxin : Physicalrequirements for cell activation. J Endotoxin Res 2005; 11:299-303.
12. Mueller M. Lindner B. Kusumoto S et al. Aggregates are the biologically active units of endotoxin. J Biol Chern 2004; 279:26307-26313. (Pubitemid 38798780)
13. Gioannini TL. Teghanemt A. Zhang D et al. Monomeric endotoxin : Protein complexes are essential for TLR4-dependent cell activation. J Endotoxin Res 2005; 11:117-123. (Pubitemid 40711488)
14. Takada H. Kotani S. Structural requirements of lipid A for endoroxiciry and other biological activities. CRC Crit Rev Microbiol1989; 16:477-523.
15. Israelachvili JN. Electrostatic Forces Between Surfaces in Lipids. Intermolecular and Surface Forces. London: Academic Press, 1991: 213-259.
16. Luzzati V. Vargas R. Mariani P et al. Cubic phases of lipid-contain ing systems. Elements of a theory and biological connotations J Mol Biol 1993; 229:540-551. (Pubitemid 23080399)
17. Mariani P. Luzzati V. Delacroix H. Cubic phases of lipid-containing systems. Structure analysis and biological implications. J Mol Biol 1993; 204:165-189.
18. Brandenburg K. Koch MHJ. Seydel U. Phase diagram of lipid A from Salmonella minnesota and Escherichia coli rough mutant lipopolysaccharide. J Struct Biol 1990; 105:11-21.
19. Seydel U. Koch MHJ, Brandenburg K. Structural polymorphism of rough mutant lipopolysaccharides Rd to Ra from Salmonella minnesota. J Strucr Biol 1993; 110:232-243.
20. Brandenburg K. Richter W; Koch MHJ et al. Characterization of the nonlamellar cubic and H ll structures of lipid A from Salmonella enterica serovar Minnesota by X-ray diffraction and freeze-fracture electron microscopy. Chern Phys Lipids 1998; 91:53-69. (Pubitemid 28056880)
21. Brandenburg K. Mayer H. Koch MHJ et al. Influence of the supramolecular structure of free lipid A on its biological activity. Eur J Biochem 1993; 218:555-563. (Pubitemid 24003773)
22. Schromm AB. Brandenburg K. Loppnow H et al. Biological activities of lipopolysaccharides are determined by the shape of their lipid A portion. Eur J Biochern 2000; 267:2008-2013. (Pubitemid 30185287)
23. Seydel U. Schromm AB. Brade L et al. Physicochemicalcharacterization of carboxymethyl lipid A derivatives in rdation to biological activity. FEBS J 2005; 272:327-340
24. Brandenburg K. Lindner B. Schromm AB et al. Physico-chemical characteristics of triacyllipid A partial structure OM-174 in relation ro biological activity. Eur J Biochem 2000; 267:3370-3377. (Pubitemid 30341167)
25. Brandenburg K. Matsuura M, Heine H et al. Biophysical characterization of triacyl monosaccharide lipid A partial structures in relation to bioactivity. Biophys J 2002; 83:322-333. (Pubitemid 34700194)
26. Brandenburg K, Andra J, Muller M et al. Physicochemical properties of bacterial glycopolymers in relation to bioactivity. Carbohydr Res 2003; 338:2477-2489. (Pubitemid 37509948)
27. Seydel U, Oikawa M, Fukase K et al. Intrinsic conformation of lipid A is responsible for agonistic and antagonistic activity. Eur J Biochern 2000; 267:3032-3039. (Pubitemid 30321351)
28. Jain MK. Nonrandom lateral organization in bilayers and biomernbranes. In: Aloia RC Membrane Fluidity in Biology, Vol. I: Concepts of Membrane Structure , New York: Academic Press, 1983: 1-37.
29. Brandenburg K, Seydel U. Physical aspects of structure and function of membranes made from lipopolysaccharides and free lipid A. Biochim Biophys Acta 1984; 775:225-238.
30. Brandenburg K, Seydel U. Investigation into the fluidity of lipopolysaccharide and free lipid A membrane systems by Fourier-transform infrared spectroscopy and differential scanninig calorimetry. Eur J Biochem 1990; 191:229-236. (Pubitemid 20219051)
31. Naumann D. Schultz C, Sabisch A et al. 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 moddling techniques J Molec Strucr 1989; 214:213-246.
32. Naumann D, Schultz C. Born Jet al.Investigations into the polymorphism of lipid A from lipopolysaccharides of Escherichia coli and Salmonella minnesota by Fourier-transform infrared spectroscopy. Eur J Biochern 1987; 164:159-169. (Pubitemid 17053680)
33. Brandenburg K. Kusumoro S, Seydel U. Conformational studies of synthetic lipid A analogues and partial structures by infrared spectroscopy. Biochim Biophys Acta 1997; 1329:193-201.
34. Toman R, Garidd P, Andrs J et al. Physicochemical characterization of the endotoxins from Coxiella burnetii strain Priscilla in relation to their bioactivities. BMC Biochem 2004; 5:1.
35. Christ WJ. Asano O, Robidoux LC et al. E5531, a pure endotoxin antagonist of high potency. Science 1995; 268:80-83.
36. Bunnell E, Lynn M, Habet K et al. A lipid A analog, E5531, blocks the endotox in response in human volunteers with experimental endoroxemia. Crit Care Med 2000; 28:2713-2720
37. Mullarkey M, Rose JR Brisrol JU et al. Inhibition of endotoxin response by E5564, a novel Toll-like receptor 4-directed endotoxin antagonist. J Pharmacol Exp Therap 2003; 304:1093-1102. (Pubitemid 36254422)
38. Lynn M, Rossignol DP, Wheder JL et al. Blocking of responses to endoroxin by E5564 in healthy volunteers with experimental endotoxernia, J Infect Diseases 2003; 187:631-639. (Pubitemid 36250027)
39. Asai Y, Iwamoro K, Watanabe S. The effect of the lipid A analog E5531 on phospholipid membrane properties FEBS Lett 1998; 438:15-20. (Pubitemid 28517827)
40. Asai Y, Iwamoto K, Watanabe S. Characterization of the physicochemical properties of aggregates of the lipid A analog, E5531, prepared by a 'pH-jump method'. Chern Phys Lipids 1999; 97:93-104. (Pubitemid 29094597)
41. Asai Y,Watanabe S. Effect of divalent cations on the membrane properties of the lipid. A analog E5531. Drug Dev Ind Pharm 1999; 25:1107-1113. (Pubitemid 29477868)
42. Gutsmann T, Schromm AB, Koch MHJ et a1. Lipopolysaccharide-binding protein-mediated interaction of lipid A from different origin with phospholipid membranes. Phys Chern Chern Phys 2000; 2:4521-4528.
43. Labischinski H, Barnickd G, Bradaczek H et al. High state of order of isolated bacterial lipopolysaccharide and its possible contribution ro the permeation barrier property of the outer membrane. J Bacreriol 1985; 162:9-20. (Pubitemid 15095824)
44. Frecer V. Ho B. Ding JL. Molecular dynamics study on lipid A from Escherichia coli: Insights into its mechanism of biological action. Biochim Biophys Acta 2000; 1466:87-104. (Pubitemid 30312968)
45. Karo N, Naito S, Arakawa Y et al. Crystallization of synthetic Escherichia coli-type lipid A. Microbiol Immunol 1996; 40:33-38. (Pubitemid 26031700)
46. Brandenburg K, Wiese A. Endoroxins: Relationships between structure , function and activity. Curr Top Med Chern 2004; 4:1127-1146. (Pubitemid 38930792)
47. Schromm AB, Brandenburg K, Loppnow H et al. The charge of endotoxin molecules influences their conformation and interleukin-6 inducing capacity. J Immunol 1998; 161:5464-5471. (Pubitemid 28519109)
48. Onier N, Hilpert S, Arnould L et al. Cure of colon cancer metastasis in rats with the new lipid A OM 174. Apoprosis of tumor cells and immunization of rats. Clin Exp Metastasis 1999; 17:299-306. (Pubitemid 29477575)
49. Reisser D, Pance A, Jeannin JE Mechanisms of the antitumoral effect of lipid A. BioEssays 2002; 24:284-289. (Pubitemid 34248695)
50. Pance A. Reisser D. Jeannin JF. Antitumoral effects of lipid A: Preclinical and clinical srudies. J Invest Med 2002; 50:173-178. (Pubitemid 34522658)
51. Larmonier CB. Arnould L. Larmonier N et al. Kinetics of tumor cell apoptosis and immune cell activation during the regression of tumors induced by lipid A in a rat model of colon cancer. Int J Mol Med 2004 ; 13:355-361.
52. Seydel U. Labischinski H. Kastowsky M et al. Phase behaviour. supramole cular structure and molecular conformation of lipopolysaccharide. Immunobiol 1993; 187:191-211. (Pubitemid 23150767)
53. Wright SD. Ramos RA. Tobias PS et al. CDI4, a receptor for complexes of lipopolysaccharide (LPS) and LPS binding protein. Science 1990; 249:1431-1433.
54. Hoshino K. Takeuchi O. Kawai T et al. Cutting edge: Toll-like receptor 4 (TLR4)-deficient mice arc hyporesponsive to lipopolysaccharide: Evidence for TLR4 as the Lps gene product. J Immunol 1999; 162:3749-3752. (Pubitemid 29314747)
55. Poltorak A. He X. Smirnova I et al. Defective LPS signaling in C3H/HeJ and C5 7BLlI0ScCr mice: Mutations in Tlr4 gene. Science 1998; 282:2085-2088. (Pubitemid 29001265)
56. Shimazu R. Akashi S. Ogata H et al. MD-2, a molecule that confers lipopolysaccharide responsiveness on Toll-like receptor 4. J Exp Med 1999; 189:1777-1782. (Pubitemid 29272694)
57. Schromm AB. Lien E. Henneke P et al. Molecular genetic analysisof an endotoxin nonresponder mutant cell Line: A point mutation in a conserved region of MD -2 abolishes endoroxin-induced signaling. J Exp Med 2001 ; 194:79-88. (Pubitemid 32660439)
58. Blunck R. Scheel O. Muller M et al. New insights inro endotoxin-induced activation of macrophages: Involvement of a K+ channel in transmembrane signaling. J Immunol 2001; 166:1009-1015. (Pubitemid 32060258)
59. + channel is involved in LPS signaling. J Endotoxin Res 2001; 7:243-247. (Pubitemid 32894581)
60. Triantafilou M. Miyake K. Golenbock DT et al. Mediators of innate immune recognition of bacteria concentrate in lipid rafts and facilitate lipopolysaccharide-induced cell activation. J Cell Sci 2002 ; 1152:2603-2611. (Pubitemid 34778077)
61. Triantafilou K. Triantafilou M. Ladha S et al. Fluorescence recovery after photobleaching reveals that LPS rapidly transfers from CD14 to hsp70 and hsp90 on the cell membrane. J Cell Sci 2001; 114:2535-2545. (Pubitemid 32684807)
62. Mueller M. Brandenburg K, Dedrick R et al. Phospholipids inhib it lipopolysaccharide (LPS)-induced cell activation: A role for LPS-binding protein. J Immunol 2005; 174:1091-1096. (Pubitemid 40094306)
63. Schumann RR. Leong SR. FlaggsGW et al. Structure and function of lipopolysaccharide binding protein Science 1990; 249 :1429-1431. (Pubitemid 120034117)
64. Hailman E. Lichenstein HS Wurfel MM et al. Lipopol ysaccharide (LPS)-binding protein accelerates the bind ing of LPS to CDI 4. J Exp Med 1994; 179:269-277.
65. Gutsmann T. Haberer N. Carroll SF et al. Interaction between lipopolysaccharide (LPS). LPS-binding prote in (LBP) and planar membranes. Biol Chern 2001 ; 382:425-434. (Pubitemid 32372486)
66. Gutsrnann T. Mueller M. Carroll SF et al. Dual role of lipopolysaccharide (LPS)-binding protein in neutralization of LPS and enhancement of LPS-induced activation of mononuclear cells. Infect Immun 2001; 69:6942-6950. (Pubitemid 32995454)
67. Roes S. Mumm F. Seydel U et al. Localization of the lipopolysaccharide- binding protein in phospholipid membranes by atomic force microscopy. J Biol Chern 2006; 281:2757-2763 (Pubitemid 43845739)
68. Gioannini TL. Teghanemt A. Zhang D et al. Isolation of an endotoxin-MD-2 complex that produces Tell-like receptor 4-dependent cell activation at picomolar concentrations. Proc Natl Acad Sci USA. 2004 ; 101:4186-4191. (Pubitemid 38405904)
69. Takayama K. Mitchell DH. Din ZZ et al. Monomeric Re lipopolysaccharide from Escherichia coli is more active than the aggregated form in the Limulus amebocyte lysate assay and in inducing Egr-I mRNA in murine peritoneal macrophages. J Biol Chern 1994; 269;2241-2244. (Pubitemid 24035438)
70. Shnyra A. Hultenby K. Lindberg AA. Role of the physical State of Salmonella lipopolysaccharide in expression of biological and endoroxic properties. Infect Immun 1993; 61:5351-5360. (Pubitemid 23353919)