Structural foundation for the design of receptor antagonists targeting Escherichia coli heat-labile enterotoxin

Structure

Volumn 5, Issue 11, 1997, Pages 1485-1499

  Merritt, Ethan A ^a   Sarfaty, Steve ^a   Feil, Ingeborg K ^a   Hol, Wim G J ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

Cholera toxin; Crystal structure; Drug design

Indexed keywords

EID: 0031573456     PISSN: 09692126     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-2126(97)00298-0     Document Type: Article

References (43)

1. Black, R.E. (1986). The epidemiology of cholera and enterotoxigenic E. coli diarrheal disease. In Developments of Vaccines and Drugs Against Diarrhea, 11th. Nobel Conf. Stockholm 1985. (Holmgren, J., Lindberg, A. & Möllby, R. eds), pp. 23-32, Studentlitteratur, Lund, Sweden.
2. Holmgren J. (1994). Receptors for cholera toxin and Escherichia coli heat-labile enterotoxin revisited. In Progress in Brain Research, Vol. 101 (Svennerholm L., et al., & Toffano G, eds), pp 163-177, Elsevier Science.
3. Moss, J., Iglewski, B., Vaughan, M. & Tu, A.T. (1995). Bacterial Toxins and Virulence Factors in Disease. Marcel Decker, Inc. New York.
4. Sixma, T.K., et al., & Hol, W.G.J. (1991). Crystal structure of a cholera toxin-related heat-labile enterotoxin from E. coli. Nature, 351, 371-378.
5. Sixma, T.K., et al., & Hol, W.G.J. (1993). Refined structure of Escherichia coli heat-labile enterotoxin, a close relative of cholera toxin. J. Mol. Biol. 230, 890-918.
6. Merritt, E.A., Pronk, S.E., Sixma, T.K., Kalk, K.H., van Zanten, B.A.M. & Hol, W.G.J. (1994). Structure of partially-activated E. coli heat-labile enterotoxin (LT) at 2.6 Å resolution. FEBS Lett. 337, 88-92.
7. Zhang, R-G., et al., & Westbrook, E.M. (1995) The three-dimensional crystal structure of cholera toxin. J. Mol. Biol. 251, 563-573.
8. Zhang, R-G., et al., & Shipley, G.G. (1995). The 2.4 Å crystal structure of cholera toxin B subunit pentamer: choleragenoid. J. Mol. Biol. 251, 550-562.
9. van den Akker, F., Merritt, E.A., Pizza, M.G., Domenighini, M., Rappuoli, R. & Hol, W.G.J. (1995). The Arg7Lys mutant of heat-labile enterotoxin exhibits great flexibility of active site loop 47-56 of the A subunit. Biochemistry 34, 10996-11004.
10. Merritt, E.A., Sarfaty, S., Pizza, M., Domenighini, M., Rappuoli, R. & Hol, W.G.J. (1995). Mutation of a buried residue causes loss of activity but no conformational change in the heat-labile enterotoxin of Escherichia coli. Nat. Struct. Biol. 2, 269-272.
11. Merritt, E.A., et al., & Hol, W.G.J. (1995). Surprising leads for a cholera toxin receptor-binding antagonist: crystallographic studies of CTB mutants. Structure 3, 561-570.
12. Merritt, E.A, et al., & Hol, W.G.J. (1997). Structural studies of receptor binding by cholera toxin mutants. Protein Sci. 6, 1516-1528.
13. Sixma, T.K., Pronk, S.E., Kalk, K.H., van Zanten, B.A.M., Berghuis, A.M. & Hol, W.G.J. (1992). Lactose binding to heat-labile enterotoxin revealed by X-ray crystallography. Nature 355, 561-564.
14. Merritt, E.A., Sixma, T.K., Kalk, K.H., van Zanten, B.A.M. & Hol, W.G.J. (1994). Galactose binding site in E. coli heat-labile enterotoxin (LT) and cholera toxin (CT). Mol. Microbiol. 13, 745-753.
15. M1 pentasaccharide. Protein Sci. 3, 166-175.
16. van den Akker, F., Steensma, E. & Hol, W.G.J. (1006). Tumor marker disaccharide D-Gal-• 1,3-GalNAc complexed to heat-labile enterotoxin from Escherichia coli. Protein Sci. 5, 1184-1188.
17. M1, and nonlipid oligosaccharide polyvalent ligands. J. Biol. Chem. 264, 13233-13237.
18. Pronk, S.E., et al., & Witholt, B. (1987). Heat-labile enterotoxin of Escherichia coli. Characterization of different crystal forms. J. Biol. Chem. 260, 13580-13584.
19. Jeffrey, G.A., Wood, R.A., Pfeffer, P.E. & Hicks, K.B. (1983). Crystal structure and solid-state NMR analysis of lactulose. J. Am. Chem. Soc. 105, 2128-2133.
20. Jeffrey, GA, Huang, D., Pfeffer, P.E., Dudley, R.L, Hicks, K.B. & Nitsch, E. (1992). Crystal structure and n.m.r. analysis of lactulose trihydrate. Carbohydrate Research 226, 29-42.
21. Hol, W.G.J. (1986). Protein crystallography and computer graphics-toward rational drug design. Angew. Chem. Int. Ed. Engl. 25, 767-778.
22. Verlinde, C.L.M.J. & Hol, W.G.J. (1994). Structure-based drug design: progress, results, and challenges. Structure 2, 577-587.
23. Brunne, R.M., Liepinsh, E., Otting, G., Wüthrich, K. & van Gunsteren, W.F. (1993). Hydration of proteins: a comparison of experimental residence times of water molecules solvating the bovine pancreatic trypsin inhibitor with theoretical model calculations. J. Mol. Biol. 231, 1040-1048.
24. Teeter, M.M. (1992). Order and disorder in water structure of crystalline proteins. Dev. Biol. Stand. 74, 63-72.
25. Karplus, P.A. & Faerman, C. (1994). Ordered water in macromolecular structure. Curr. Opin. Struct. Biol. 4, 770-776.
26. Engh, R.A., et al., & von der Saal, W. (1996). Enzyme flexibility, solvent and 'weak' interactions characterize thrombin-ligand interactions: implications for drug design. Structure 15, 1353-1362.
27. Lam, P.Y., et al., & Erickson-Viitanen, S. (1994). Rational design of potent, bioavailable, nonpeptide cyclic ureas as HIV protease inhibitors. Science 263, 380-384.
28. Burke, T.R. Jr., et al., & Barford, D. (1996). Small molecule interactions with protein-tyrosine phosphatase PTP1B and their use in inhibitor design. Biochemistry 35, 15989-15996.
29. Thaisrivongs, S., et al., & Watenpaugh, K.D. (1996). Structure-based design of HIV protease inhibitors: 5,6-dihydro-4-hydroxy-2-pyrones as effective, nonpeptidic inhibitors. J. Med. Chem. 39, 4630-4642.
30. Finkelstein, R.A., Burks, M.F., Zupan, A., Dallas, W.S., Jacob, C.O. & Ludwig, D.S. (1987). Epitopes of the cholera family of enterotoxins. Rev. Infect. Diseases 9, 544-561.
31. Domenighini, M., Pizza, M., Jobling, M.G., Holmes, R.K. & Rappuoli, R. (1995). Identification of errors among database sequence entries and comparison of correct amino acid sequences for the heat-labile enterotoxins of Escherichia coli and Vibrio cholerae. Mol. Microbiol. 15, 1165-1167.
32. Feil, I.K., et al., & Hol, W.G.J. (1996). Protein engineering studies of A chain loop 47 to 56 of Escherichia coli heat-labile enterotoxin point to a a prominent role of this loop for cytotoxicity. Mol. Microbiol. 20, 823-832.
33. Uesaka, Y., Otsuka, Y., Lin, Z., Yamasaki, S., Kurazono, H. & Takeda, Y. (1994). Simple method of purification of Escherichia coli heat-labile enterotoxin and cholera toxin using immobilized galactose. Microbiol Path. 16, 71-76.
34. Navaza, J. (1994). AMoRe: an automated package for molecular replacement. Acta Cryst. A 50, 157-163.
35. McRee D. (1993). Practical Protein Crystallography. Academic Press, San Diego.
36. Brünger, A. (1990). X-PLOR (Version 3.0) Manual. Yale University, New Haven, CT.
37. Sixma, T.K., Aguirre, A., van Scheltinga, A.C.T., Wartna, E.S., Kalk, K.H. & Hol, W.G.J. (1992). Heat-labile enterotoxin crystal forms with variable A/B5 orientation. FEBS Letters 305, 81-85.
38. CCP4 (1979). The SERC (UK) Collaborative Computing Project No. 4, a Suite of Programs for Protein Crystallography, distributed from Daresbury Laboratory, Warrington WA4 4AD, UK.
39. Merritt, E.A. & Bacon, DJ. (1997). Raster3D: photorealistic molecular graphics. Methods Enzymol. 277, in press.
40. Wallace, A.C., Laskowski, R.A. & Thornton, J.M. (1995). LIGPLOT: a program to generate schematic diagrams of protein-ligand interactions. Protein Eng. 8, 127-134.
41. Nicholls, A., Bharadwaj, R. & Honig, B. (1993). GRASP: graphical representation and analysis of surface properties. Biophys. J. 64, 166-170.
42. M1 Biochemistry 28, 5019-5024.
43. Connolly, M. L. (1983). Analytical molecular surface calculation. J. Appl. Cryst. 16, 548-558.