Solution structure of polymyxins B and E and effect of binding to lipopolysaccharide: An NMR and molecular modeling study

Journal of Medicinal Chemistry

Volumn 42, Issue 22, 1999, Pages 4604-4613

  Pristovšek, Primož ^a,b   Kidrič, Jurka ^a  

^a NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

^b GOETHE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

COLISTIN; POLYMYXIN B;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DRUG BINDING; DRUG STRUCTURE; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

ANTI-BACTERIAL AGENTS; COLISTIN; LIPOPOLYSACCHARIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; POLYMYXIN B; SOLUTIONS; WATER;

EID: 0033524028     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm991031b     Document Type: Article

References (51)

1. Fearon, D. T.; Locksley, R. M. The instructive role of the innate immunity in the acquired immune response. Science 1996, 272, 50-54.
2. Ulevitch, R. J.; Tobias, P. S. Recognition of endotoxin by cells leading to transmembrane signaling. Curr. Opin. Immunol. 1994, 6, 125-130.
3. Chapman, T. M.; Golden, M. R. Polymyxin B. NMR evidence for a peptide antibiotic with folded structure in water. Biochem. Biophys. Res. Commun. 1972, 46, 2040-2047.
4. Rustici, A.; Velucchi, M.; Faggioni, R.; Sironi, M.; Ghezzi, P.; Quataert, S.; Green, B.; Porro, M. Molecular mapping and detoxification of the lipid A binding site by synthetic peptides. Science 1993, 259, 361-365.
5. Taylor, A. H.; Heavner, G.; Nedelman, M.; Sherris, D.; Brunt, E.; Knight, D.; Ghrayeb, J. Lipopolysaccharide (LPS) neutralizing peptides reveal a lipid A binding site of LPS binding protein. J. Biol. Chem. 1995, 270, 17934-17938.
6. Battafarano, R. J.; Dahlberg, P. S.; Ratz, C. A.; Johnston, J. W.; Gray, B. H.; Haseman, J. R.; Mayo, K. H.; Dunn, D. L. Peptide derivatives of three distinct lipopolysaccharide binding proteins inhibit lipopolysaccharide-induced tumor necrosos factor-alpha secretion in vitro. Surgery 1995, 118, 318-324.
7. Ried, C.; Wahl, C.; Miethke, T.; Wellnhofer, G.; Landgraf, C.; Schneider-Mergener, J.; Hoess, A. High affinity endotoxin-binding and neutralizing peptides based on the crystal structure of recombinant limulus anti-lipopolysaccharide factor. J. Biol. Chem. 1996, 271, 28120-28127.
8. Kloczewiak, M.; Black, K. M.; Loiselle, P.; Cavaillon, J. M.; Wainwright, N.; Warren, H. S. Synthetic peptides that mimic the binding site of horseshoe crab antilipopolysaccharide factor. J. Infect. Dis. 1994, 170, 1490-1497.
9. Gray, B. H.; Haseman, J. R.; Mayo, K. H. B/PI-derived synthetic peptides: synergistic effects in tethered bactericidal and endotoxin neutralizing peptides. Biochim. Biophys. Acta 1994, 1244, 185-190.
10. Pereira, H. A.; Erdem, I.; Pohl, J.; Spitznagel, J. K. Synthetic bactericidal peptide based on CAP37: a 37-kDa human neutrophil granule-associated cationic antimicrobial protein chemotactic for monocytes. Immunology 1993, 90, 4733-4737.
11. Rietschel, E. T.; Brade, L.; Holst, O.; Kulshin, V. A.; Lindner, B.; Moran, A. P.; Schade, U. F.; Zaehringer, U.; Brade, H. Molecular structure of bacterial endotoxin in relation to bioactivity. In Cellular and molecular aspects of endotoxin reactions; Nowotny, A., Spitzer, J. J., Ziegler, E. J., Eds.; Elsevier Science Publishers B.V.: Amsterdam, 1990; pp 15-32.
12. Kirikae, T.; Schade, F. U.; Zaehringer, U.; Kirikae, F.; Brade, H.; Kusumoto, S.; Kusama, T.; Rietschel, E. T. The significance of the hydrophilic backbone and the hydrophobic fatty acid regions of lipid A for macrophage binding and cytokine induction. FEMS Immunol. Med. Microbiol. 1994, 8, 13-26.
13. Seydel, U.; Labischinski, H.; Kastowsky, M.; Brandenburg, K. Phase behaviour, supramolecular structure, and molecular conformation of lipopolysaccharide. Immunobiology 1993, 187, 191-211.
14. Zaehringer, U.; Lindner, B.; Seydel, U.; Rietschel, E. T.; Naoki, H.; Unger, F. M.; Imoto, M.; Kusumoto, S.; Shiba, T. Structure of de-O-acylated lipopolysaccharide from the Escherichia coli Re mutant strain F 515. Tetrahedron Lett. 1986, 26, 6321-6324.
15. Helander, I. M.; Kilpelaeinen, I.; Vaara, M.; Moran, A. P.; Lindner, B.; Seydel, U. Chemical structure of the lipid A component of lipopolysaccharides of the genus Pectinatus. Eur. J. Biochem. 1994, 224, 63-70.
16. Vinogradov, V.; Bock, K.; Holst, O.; Brade, H. The structure of the lipid A - core region of the lipopolysaccharide from Vibro cholerae O1 smooth strain 569B (Inaba) and rough mutant strain 95R (Ogawa). Eur. J. Biochem. 1995, 233, 152-158.
17. Kastowsky, M.; Gutberlet, T.; Bradaczek, H. Molecular modelling of the three-dimensional structure and conformational flexibility of bacterial lipopolysaccharide. J. Bacteriol. 1992, 174, 4798-4806.
18. 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. 1993, 217, 771-779.
19. Wistroem, C. A.; Jones, G. M.; Tobias, P. S.; Sklar, L. A. Fluorescence resonance energy transfer analysis of lipopolysaccharide in detergent micelles. Biophys. J. 1996, 70, 988-997.
20. Labischinski, H.; Vorgel, E.; Uebach, W.; May, R. P.; Bradaczek, H. Architecture of bacterial lipid A in solution-a neutron small-angle scattering study. Eur. J. Biochem. 1990, 190, 359-363.
21. Jung, S.; Min, D.; Hollingsworth, R. I. A Metropolis Monte carlo method for analysing the energetics and dynamics of lipopolysaccharide supramolecular structure and organization. J. Comput. Chem. 1996, 17, 238-249.
22. 2+. Biophys. J. 1997, 72, 1031-1046.
23. Hoess, A.; Watson, S.; Silber, G. R.; Liddington, R. Crystal structure of an endotoxin-neutralizing protein from the horeshoe crab, Limulus anti-LPS factor, at 1.5 A resolution. EMBO J. 1993, 12, 3351-3356.
24. Morrison, D. C.; Jacobs, D. M. Binding of polymyxin b to the lipid A portion of bacterial lipopolysaccharide. Immunochemistry 1976, 13, 813-818.
25. David, S. A.; Balasubramanian, K. A.; Mathan, V. I.; Balaram, P. Analysis of the binding of polymyxin B to endotoxic lipid A and core glycolipid using a fluorescent displacement probe. Biochim. Biophys. Acta 1992, 1165, 145-152.
26. Cajal, Y.; Rogers, J.; Berg, O. G.; Jain, M. K. Intermembrane molecular contacts by polymyxin B mediate exchange of phospholipids. Biochemistry 1996, 35, 299-308.
27. Amir, S.; Sasson, S.; Kaiser, N.; Meyerovitch, J.; Schechter, Y. Polymyxin B is an inhibitor of insulin-induced hypoglycemia in the whole animal model. Studies on the mode of inhibitory action. J. Biol. Chem. 1987, 262, 6663-6667.
28. David, S. A.; Awasthi, S. K.; Wiese, A.; Ulmer, A. J.; Lindner, B.; Brandenburg, K.; Seydel, U.; Rietschel, E. T.; Sonneson, A.; Balaram, P. Characterisation of the interactions of a polycationic, amphiphilic, terminally branched oligopeptide with lipid A and lipopolysaccharide from the deep rough mutant of Salmonella minnesota. J. Endotoxin Res. 1996, 3, 369-379.
29. Macura, S.; Kumar, N. K.; Brown, L. R. Combined use of COSY and double-quantum two-dimensional NMR spectroscopy for elucidation of spin systems in polymyxin B. Biochem. Biophys. Res. Commun. 1983, 117, 486-492.
30. Liao, S. Y.; Ong, G. T.; Wang, K. T.; Wu, S. H. Conformation of polymyxin B analogs in DMSO from NMR spectra and molecular modelling. Biochim. Biophys. Acta 1995, 1252, 312-320.
31. Bhattacharjya, S.; David, S. A.; Mathan, V. I.; Balaram, P. Polymyxin B nonapeptide: conformations in water and in the lipopolysaccharide-bound state determined by two-dimensional NMR and molecular dynamics. Biopolymers 1997, 41, 251-265.
32. Srimal, S.; Surolia, N.; Balasubramanian, S.; Surolia, A. Titration calorimetric studies to elucidate the specificity of the interactions of polymyxin B with lipopolysaccharides and lipid A. Biochem. J. 1996, 315, 679-686.
33. Dyson, H. J.; Wright, P. E. Defining solution conformations of small linear peptides. Annu. Rev. Biophys. Biophys. Chem. 1991, 20, 519-538.
34. Wilmot, C. M.; Thornton, J. M. β-Turns and their distortions: a proposed new nomenclature. Protein Eng. 1990, 3, 479-493.
35. Pristovšek, P.; Kidrič, J. NMR and molecular dynamics study of muroctasin-implications for the bioactive conformation. Biopolymers 1997, 42, 671.
36. Nicklaus, M. C.; Wang, S.; Driscoll, J. S.; Milne, G. W. A. Conformational Changes of Small Molecules Binding to Proteins. Bioorg. Med. Chem. 1995, 3, 411-428.
37. Clore, G. M.; Gronenborn, A. M. Theory and applications of the transferred nuclear Overhauser effect to the study of the conformations of small ligands bound to proteins. J. Magn. Reson. 1982, 48, 402-417.
38. Gegner, J. A.; Ulevitch, R. J.; Tobias, P. S. Lipopolysaccharide (LPS) Signal Transduction and Clearance. J. Biol. Chem. 1995, 270, 5320-5325.
39. Koch, P. J.; Frank, J.; Schuler, J.; Kahle, C.; Bradaczek, H. Thermodynamics and structural studies of the interaction of polymyxin B with deep rough mutant lipopolysaccharides. J. Colloid Interface Sci. 1999, 213, 557-564.
40. Carpenter, C. L.; Cantley, L. C. A flattened face for membranes. Nature Struct. Biol. 1998, 5, 843-845.
41. Schindler, M.; Osborn, M. J. Interaction of divalent cations and polymyxin B with lipopolysaccharide. Biochemistry 1979, 18, 4425-4430.
42. Pleiss, J.; Fischer, M.; Schmid, R. D. Anatomy of lipase binding sites: the scissile fatty acid binding site. Chem. Phys. Lipids 1998, 93, 67-80.
43. Lang, D. A.; Dijkstra, B. W. Structural investigationsof the regio-and enantioselectivity of lipases. Chem. Phys. Lipids 1998, 67, 115-122.
44. Wang, Y.; Hollingsworth, R. I. An NMR Spectroscopy and Molecular Mechanics Study of the Molecular Basis for Supramolecular Structure of Lipopolysaccharides. Biochemistry 1996, 35, 5647-5654.
45. Piantini, U.; Sorensen, O. W.; Ernst, R. R. Multiple quantum filters for elucidating NMR coupling networks. J. Am. Chem. Soc. 1982, 104, 6800-6801.
46. Braunschweiler, L.; Ernst, R. R. Coherence transfer by isotropic mixing: application to proton correlation spectroscopy. J. Magn. Reson. 1983, 53, 521-528.
47. Jeneer, J.; Meier, B. H.; Bachman, P.; Ernst, R. R. Investigations of exchange processes by two-dimensional NMR spectroscopy. J. Chem. Phys. 1979, 71, 4546-4553.
48. Bothner-By, A. A.; Stephens, R. L.; Lee, J.; Warren, C. D.; Jeanloz, R. W. Structure determination of a tetrasaccharide: transient nuclear overhauser effects in the rotating frame. J. Am. Chem. Soc. 1984, 106, 811-813.
49. Piotto, M.; Saudek, V.; Sklenar, V. Gradient-tailored excitation for single-quantum NMR spectroscopy of aqueous solutions. J. Biomol. NMR 1992, 2, 661-665.
50. Gronenborn, A. M.; Clore, G. M. Conformation of NAD+ bound to yeast and horse liver alcohol dehydrogenase in solution. The use of the proton-proton transferred nuclear Overhauser enhancement. J. Mol. Biol. 1982, 157, 155-160.
51. Dauber-Ogusthorpe, P.; Roberts, V. A.; Ogusthorpe, D. J.; Wolff, D. J.; Genest, M.; Hagler, A. T. Structure and energetics of ligand binding to proteins: Escherichia coli dihydrofolate reductase-trimethoprim, a drug-receptor system. Proteins Struct. Funct. Genet. 1988, 4, 31-47.