Structure-based discovery of a pore-binding ligand: Towards assembly inhibitors for cholera and related AB5 toxins

Journal of Molecular Biology

Volumn 285, Issue 3, 1999, Pages 1169-1178

  Hovey, Bianca T ^b   Verlinde, Christophe L M J ^b   Merritt, Ethan A ^b   Hol, Wim G J ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

^b NONE

Author keywords

Drug design; Heat labile enterotoxin; Protein crystallography; Triazolium

Indexed keywords

CHOLERA TOXIN; ENTEROTOXIN;

ARTICLE; CARBOXY TERMINAL SEQUENCE; CRYSTAL STRUCTURE; ESCHERICHIA COLI; LIGAND BINDING; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; PROTEIN STRUCTURE; TOXIN SYNTHESIS;

ESCHERICHIA COLI;

EID: 0004758773     PISSN: 00222836     EISSN: None     Source Type: Journal    
DOI: 10.1006/jmbi.1998.2340     Document Type: Article

References (40)

1. 5quaternary structure of cholera toxin. EMBO J. 15:1996;4246-4253.
2. Brünger, A. T. 1992, X-PLOR Version 3.1 a System for X-ray Crystallography and NMR, Yale University Press, New Haven, CT.
3. Doleschall G. A novel method of conversion of primary amines into aldehydes. Tetrahedron Letters. 24:1978;2131-2132.
4. Feil I. K., Reddy R., de Haan L., Merritt E. A., van den Akker F., Storm D. R., Hol W. G. Protein engineering studies of A-chain loop 47-56 of Escherichia coli heat-labile enterotoxin point to a prominent role of this loop for cytotoxicity. Mol. Microbiol. 20:1996;823-832.
5. Fraser M. E., Chernaia M. M., Kozlov Y. V., James M. N. Crystal structure of the holotoxin from Shigella dysenteriae at 2.5 Å resolution. Nature Struct. Biol. 1:1994;59-64.
6. Hardy S. J., Holmgren J., Johansson S., Sanchez J., Hirst T. R. Coordinated assembly of multisubunit proteins: oligomerization of bacterial enterotoxins in vivo and in vitro. Proc. Natl Acad. Sci. USA. 85:1988;7109-7113.
7. Hirst T. R. Moss J., Igleweski B., Vaughan M., Tu A. T. Bacterial Toxins and Virulence Factors in Disease. 1995;123-184 Marcel Dekker, Inc. New York.
8. Hirst T. R., Holmgren J. Conformation of protein secreted across bacterial outer membranes: a study of enterotoxin translocation from Vibrio cholerae. Proc. Natl Acad. Sci. USA. 84:1987;7418-7422.
9. Hirst T. R., Sanchez J., Kaper J. B., Hardy S. J., Holmgren J. Mechanism of toxin secretion by Vibrio cholerae investigated in strains harboring plasmids that encode heat-labile enterotoxins of Escherichia coli. Proc. Natl Acad. Sci. USA. 81:1984;7752-7756.
10. Hofstra H., Witholt B. Kinetics of synthesis, processing, and membrane transport of heat-labile enterotoxin, a periplasmic protein inEscherichia coli. J. Biol. Chem. 259:1984;15182-15187.
11. Hol W. G. J. The role of the α-helix dipole in protein structure and function. Prog. Biophys. Mol. Biol. 45:1985;149-195.
12. Hubbard S. J., Thornton J. M. "NACCESS", computer program. 1993;University College London, Department of Biochemistry and Molecular Biology, London.
13. Kraulis P. J. MOLSCRIPT: a program to produce both detailed and schematic plots of protein structures. J. Appl. Crystallog. 24:1991;946-950.
14. Laskowski R. A., MacArthur M. W., Moss D. S., Thornton J. M. PROCHECK: a program to check the stereochemical quality of protein structures. J. Appl. Crystallog. 26:1993;283-291.
15. McRee D. E. Practical Protein Crystallography. 1993;Academic Press, San Diego.
16. Merritt E. A., Bacon D. J. Raster3D photorealistic molecular graphics. Methods Enzymol. 277:1997;505-524.
17. Merritt E. A., Sarfaty S., van den Akker F., L'Hoir C., Martial J. A., Hol W. G. J. Crystal structure of cholera toxin B-pentamer bound to receptor GM1 pentasaccharide. Protein Sci. 3:1994a;166-175.
18. Merritt E. A., Sixma T. K., Kalk K. H., van Zanten B. A., Hol W. G. J. Galactose-binding site in Escherichia coli heat-labile enterotoxin (LT) and cholera toxin (CT). Mol. Microbiol. 13:1994b;745-753.
19. Merritt E. A., Sarfaty S., Feil I. K., Hol W. G. J. Structural foundation for the design of receptor antagonists targeting Escherichia coli heat-labile enterotoxin. Structure. 5:1997;1485-1499.
20. M1-pentasaccharide. J. Mol. Biol. 282:1998;1043-1059.
21. Moss J., Vaughan M. ADP-ribosylation of guanyl nucleotide-binding regulatory proteins by bacterial toxins. Advances in Enzymology and Related Areas of Molecular Biology. 1988;. p. 303-379.
22. Navaza J. AMoRe: an automated package for molecular replacement. Acta Crystallog. sect. A. 50:1994;157-163.
23. Otwinowski Z., Minor W. Processing of X-ray diffraction data collected in oscillation mode. Carter C. W. Jr, Sweet R. M. Methods in Enzymology. 1996;307-326 Academic Press, New York.
24. Read R. Improved Fourier coefficients for maps using phases from partial structures with errors. Acta Crystallog. sect. A. 42:1986;140-149.
25. Shuker S. B., Hajduk P. J., Meadows R. P., Fesik S. W. Discovering high-affinity ligands for proteins: SAR by NMR. Science. 274:1996;1531-1534.
26. Sixma T. K., Pronk S. E., Kalk K. H., Wartna E. S., van Zanten B. A., Witholt B., Hol W. G. J. Crystal structure of a cholera toxin-related heat-labile enterotoxin from E. coli (see comments). Nature. 351:1991;371-377.
27. Sixma T. K., Pronk S. E., Kalk K. H., van Zanten B. A., Berghuis A. M., Hol W. G. Lactose binding to heat-labile enterotoxin revealed by X-ray crystallography. Nature. 355:1992;561-564.
28. Sixma T. K., Kalk K. H., van Zanten B. A., Dauter Z., Kingma J., Witholt B., Hol W. G. J. Refined structure of Escherichia coli heat-labile enterotoxin, a close relative of cholera toxin. J. Mol. Biol. 230:1993a;890-918.
29. Sixma T. K., Stein P. E., Hol W. G. J., Read R. J. Comparison of the B-pentamers of heat-labile enterotoxin and verotoxin-l: two structures with remarkable similarity and dissimilarity. Biochemistry. 32:1993b;191-198.
30. Spangler B. D. Structure and function of cholera toxin and the related Escherichia coli heat-labile enterotoxin. Microbiol. Rev. 56:1992;622-647.
31. Sprang S. R. G protein mechanisms: insights from structural analysis. Annu. Rev. Biochem. 66:1997;639-678.
32. Stein P. E., Boodhoo A., Tyrrell G. J., Brunton J. L., Read R. J. Crystal structure of the cell- binding B oligomer of verotoxin-1 from E. coli. Nature. 355:1992;748-750.
33. Streatfield S. J., Sandkvist M., Sixma T. K., Bagdasarian M., Hol W. G. J., Hirst T. R. Intermolecular interactions between the A and B subunits of heat-labile enterotoxin from Escherichia coli promote holotoxin assembly and stability in vivo. Proc. Natl Acad. Sci. USA. 89:1992;12140-12144.
34. Takeda Y., Honda T., Taga S., Miwatani T. In vitro formation of hybrid toxins between subunits of Escherichia coli heat-labile enterotoxin and those of cholera enterotoxin. Infect. Immun. 34:1981;341-346.
35. Taylor R., Kennard O. Crystallographic evidence for the existence of C-H···O, C-H···N, and C-H···Cl hydrogen bonds. J. Am. Chem. Soc. 104:1982;5063-5070.
36. Van Calenbergh S., Verlinde C. L., Soenens J., De Bruyn A., Callens M., Blaton N. M., Peeters O. M., Rozenski J., Hol W. G., Herdewijn P. Synthesis and structure-activity relationships of analogs of 2′-deoxy-2′-(3-methoxybenzamido) adenosine, a selective inhibitor of trypanosomal glycosomal glyceraldehyde-3-phosphate dehydrogenase. J. Med. Chem. 38:1995;3838-3849.
37. Van den Akker F., Sarfaty S., Twiddy E. M., Connell T. D., Holmes R. K., Hol W. G. J. Crystal structure of a new heat-labile enterotoxin, LT-IIb. Structure. 4:1996;665-678.
38. Van Dop C., Tsubokawa M., Bourne H. R., Ramachandran J. Amino acid sequence of retinal transducin at the site ADP-ribosylated by cholera toxin. J. Biol. Chem. 259:1984;696-698.
39. Verlinde C. L., Merritt E. A., van den Akker F., Kim H., Feil I., Delboni L. F., Mande S. C., Sarfaty S., Petra P. H., Hol W. G. J. Protein crystallography and infectious diseases. Protein Sci. 3:1994;1670-1686.
40. Zhang R. G., Scott D. L., Westbrook M. L., Nance S., Spangler B. D., Shipley G. G., Westbrook E. M. The three-dimensional crystal structure of cholera toxin. J. Mol. Biol. 251:1995;563-573.