Crystal structures of Trypanosoma brucei sterol 14α-demethylase and implications for selective treatment of human infections

Journal of Biological Chemistry

Volumn 285, Issue 3, 2010, Pages 1773-1780

  Lepesheva, Galina I ^a   Park, Hee Won ^b   Hargrove, Tatiana Y ^a   Vanhollebeke, Benoit ^c   Wawrzak, Zdzislaw ^d   Harp, Joel M ^a   Sundaramoorthy, Munirathinam ^a   Nes, W David ^e   Pays, Etienne ^c   Chaudhuri, Minu ^f   Villalta, Fernando ^f   Waterman, Michael R ^a  

^a VANDERBILT UNIVERSITY   (United States)

^b UNIVERSITY OF TORONTO   (Canada)

^c UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

^d NORTHWESTERN UNIVERSITY   (United States)

^e TEXAS TECH UNIVERSITY   (United States)

^f MEHARRY MEDICAL COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SITE; AMIDE GROUPS; ANTIPARASITIC DRUGS; BENZAMIDES; BINDING MODES; CYTOCHROME P450; DEMETHYLASE; DIRECTED DESIGN; DRUG TARGETS; FUNGAL DISEASE; HUMAN INFECTION; HUMAN PATHOGENS; HYDROGEN BOND NETWORKS; IMIDAZOL; IRREVERSIBLE EFFECTS; LIGAND-FREE; MYCOBACTERIUM TUBERCULOSIS; ORTHOLOGS; PROTEIN SEGMENTS; SELECTIVE TREATMENT; STEROL BIOSYNTHESIS; TRYPANOSOMA BRUCEI;

ALCOHOLS; AMIDES; BINDING ENERGY; BIOCHEMISTRY; BIOSYNTHESIS; ENZYMES; HYDROGEN BONDS; PATHOGENS; PORPHYRINS; PROTOZOA; REACTION KINETICS;

ENZYME ACTIVITY;

AMIDE; ANTIPARASITIC AGENT; HEME; N 1 (2,4 DICHLOROPHENYL) 2 [(1H IMIDAZOL 1 YL)ETHYL] 4 (5 PHENYL 1,3,4 OXADIAZOL 2 YL)BENZAMIDE; STEROL 14ALPHA DEMETHYLASE; STEROL 14ALPHA DEMETHYLASE INHIBITOR; UNCLASSIFIED DRUG; ANTITRYPANOSOMAL AGENT; BENZAMIDE; BENZAMIDE DERIVATIVE; CYTOCHROME P450; ENZYME INHIBITOR; LANOSTEROL 14 ALPHA-DEMETHYLASE; LIGAND; STEROL;

AFRICAN TRYPANOSOMIASIS; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG DESIGN; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME CONFORMATION; ENZYME SUBSTRATE; EUKARYOTE; HYDROGEN BOND; LIPOGENESIS; MICROSOME; MOUSE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; ORTHOLOGY; PRIORITY JOURNAL; PROTEIN FAMILY; TRYPANOSOMA BRUCEI; AMINO ACID SEQUENCE; BIOCATALYSIS; BIOSYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; ENZYME SPECIFICITY; ENZYMOLOGY; HUMAN; METABOLISM; PROTEIN CONFORMATION; X RAY CRYSTALLOGRAPHY;

EUKARYOTA; MYCOBACTERIUM TUBERCULOSIS; PROTOZOA; TRYPANOSOMA BRUCEI; TRYPANOSOMATIDAE;

AMINO ACID SEQUENCE; BENZAMIDES; BIOCATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYTOCHROME P-450 ENZYME SYSTEM; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; LIGANDS; MICROSOMES; MODELS, MOLECULAR; PROTEIN CONFORMATION; STEROLS; SUBSTRATE SPECIFICITY; TRYPANOCIDAL AGENTS; TRYPANOSOMA BRUCEI BRUCEI; TRYPANOSOMIASIS, AFRICAN;

EID: 76249100348     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M109.067470     Document Type: Article

References (48)

1. Barrett, M. P., Burchmore, R. J., Stich, A., Lazzari, J. O., Frasch, A. C., Cazzulo, J. J., and Krishna, S. (2003) Lancet 362, 1469-1480
2. Croft, S. L., Barrett, M. P., and Urbina, J. A. (2005) Trends Parasitol. 21, 508-512
3. Myler, P. J. (2008) Adv. Exp. Med. Biol. 625, 133-140
4. Soeiro, M. N., and de Castro, S. L. (2009) Expert. Opin. Ther. Targets 13, 105-121
5. Lüscher, A., de Koning, H. P., and Mäser, P. (2007) Curr. Pharm. Des. 13, 555-567
6. Cruz, A. K., de Toledo, J. S., Falade, M., Terrão, M. C., Kamchonwongpaisan, S., Kyle, D. E., and Uthaipibull, C. (2009) Curr. Drug Targets 10, 178-192
7. Como, J. A., and Dismukes, W. E. (1994) N. Engl. J. Med. 330, 263-272
8. Thompson, G. R., 3rd, Cadena, J., and Patterson, T. F. (2009) Clin. Chest. Med. 30, 203-215
9. Lepesheva, G. I., and Waterman, M. R. (2007) Biochim. Biophys. Acta 1770, 467-477
10. Buckner, F., Yokoyama, K., Lockman, J., Aikenhead, K., Ohkanda, J., Sadilek, M., Sebti, S., Van Voorhis, W., Hamilton, A., and Gelb, M. H. (2003) Proc. Natl. Acad. Sci. U.S.A. 100, 15149-15153
11. Lepesheva, G. I., Ott, R. D., Hargrove, T. Y., Kleshchenko, Y. Y., Schuster, I., Nes, W. D., Hill, G. C., Villalta, F., and Waterman, M. R. (2007) Chem. Biol. 14, 1283-1293
12. Konkle, M. E., Hargrove, T. Y., Kleshchenko, Y. Y., von Kries, J. P., Ridenour, W., Uddin, M. J., Caprioli, R. M., Marnett, L. J., Nes, W. D., Villalta, F., Waterman, M. R., and Lepesheva, G. I. (2009) J. Med. Chem. 52, 2846-2853
13. Lepesheva, G. I., Hargrove, T. Y., Kleshchenko, Y., Nes, W. D., Villalta, F., and Waterman, M. R. (2008) Lipids 43, 1117-1125
14. Lepesheva, G. I., Nes, W. D., Zhou, W., Hill, G. C., and Waterman, M. R. (2004) Biochemistry 43, 10789-10799
15. von Wachenfeldt, C., Richardson, T. H., Cosme, J., and Johnson, E. F. (1997) Arch. Biochem. Biophys. 339, 107-114
16. Otninowski, Z., and Minor, W. (1995) HKL Manual, Yale University, New Haven, CT
17. Terwilliger, T. C., and Berendzen, J. (1999) Acta Crystallogr. D 55, 849-861
18. Collaborative Computational Project Number 4 (1994) Acta Crystallogr. D 50, 760-763
19. Terwilliger, T. C. (2000) Acta Crystallogr. D 56, 965-972
20. Jones, T. A., Zou, J. Y., Cowan, S. W., and Kjeldgaard, M. (1991) Acta Crystallogr. A 47, 110-119
21. Emsley, P., and Cowtan, K. (2004) Acta Crystallogr. D 60, 2126-2132
22. Kleywegt, G. J., and Jones, T. A. (1994) Acta Crystallogr. D 50, 178-185
23. Vanhollebeke, B., De Muylder, G., Nielsen, M. J., Pays, A., Tebabi, P., Dieu, M., Raes, M., Moestrup, S. K., and Pays, E. (2008) Science 320, 677-681
24. Brun, R., and Jenni, L. (1977) Acta Trop. 34, 21-33
25. Podust, L. M., Poulos, T. L., and Waterman, M. R. (2001) Proc. Natl. Acad. Sci. U.S.A. 98, 3068-3073
26. Ghosh, D., Griswold, J., Erman, M., and Pangborn, W. (2009) Nature 457, 219-223
27. Mast, N., White, M. A., Bjorkhem, I., Johnson, E. F., Stout, C. D., and Pikuleva, I. A. (2008) Proc. Natl. Acad. Sci. U.S.A. 105, 9546-9551
28. Williams, P. A., Cosme, J., Sridhar, V., Johnson, E. F., and McRee, D. E. (2000) Mol. Cell 5, 121-131
29. Hasemann, C. A., Kurumbail, R. G., Boddupalli, S. S., Peterson, J. A., and Deisenhofer, J. (1995) Structure 3, 41-62
30. Poulos, T. L. (2007) Drug Metab. Rev. 39, 557-566
31. Guallar, V., Baik, M. H., Lippard, S. J., and Friesner, R. A. (2003) Proc. Natl. Acad. Sci. U.S.A. 100, 6998-7002
32. Lepesheva, G. I., Zaitseva, N. G., Nes, W. D., Zhou, W., Arase, M., Liu, J., Hill, G. C., and Waterman, M. R. (2006) J. Biol. Chem. 281, 3577-3585
33. Lepesheva, G. I., Virus, C., and Waterman, M. R. (2003) Biochemistry 42, 9091-9101
34. Schlichting, I., Berendzen, J., Chu, K., Stock, A. M., Maves, S. A., Benson, D. E., Sweet, R. M., Ringe, D., Petsko, G. A., and Sligar, S. G. (2000) Science 287, 1615-1622
35. McLean, K. J., Dunford, A. J., Sabri, M., Neeli, R., Girvan, H. M., Balding, P. R., Leys, D., Seward, H. E., Marshall, K. R., and Munro, A. W. (2006) Biochem. Soc. Trans. 34, 1178-1182
36. Podust, L. M., Yermalitskaya, L. V., Lepesheva, G. I., Podust, V. N., Dalmasso, E. A., and Waterman, M. R. (2004) Structure 12, 1937-1945
37. Lepesheva, G. I., Podust, L. M., Bellamine, A., and Waterman, M. R. (2001) J. Biol. Chem. 276, 28413-28420
38. Bellamine, A., Lepesheva, G. I., and Waterman, M. R. (2004) J. Lipid Res. 45, 2000-2007
39. Matsuura, K., Yoshioka, S., Tosha, T., Hori, H., Ishimori, K., Kitagawa, T., Morishima, I., Kagawa, N., and Waterman, M. R. (2005) J. Biol. Chem. 280, 9088-9096
40. Lepesheva, G. I., Seliskar, M., Knutson, C. G., Stourman, N. V., Rozman, D., and Waterman, M. R. (2007) Arch. Biochem. Biophys. 464, 221-227
41. Ekroos, M., and Sjögren, T. (2006) Proc. Natl. Acad. Sci. U.S.A. 103, 13682-13687
42. Berriman, M., Ghedin, E., Hertz-Fowler, C., Blandin, G., Renauld, H., Bartholomeu, D. C., Lennard, N. J., Caler, E., Hamlin, N. E., Haas, B., Böhme, U., Hannick, L., Aslett, M. A., Shallom, J., Marcello, L., Hou, L., Wickstead, B., Alsmark, U. C., Arrowsmith, C., Atkin, R. J., Barron, A. J., Bringaud, F., Brooks, K., Carrington, M., Cherevach, I., Chillingworth, T. J., Churcher, C., Clark, L. N., Corton, C. H., Cronin, A., Davies, R. M., Doggett, J., Djikeng, A., Feldblyum, T., Field, M. C., Fraser, A., Goodhead, I., Hance, Z., Harper, D., Harris, B. R., Hauser, H., Hostetler, J., Ivens, A., Jagels, K., Johnson, D., Johnson, J., Jones, K., Kerhornou, A. X., Koo, H., Larke, N., Landfear, S., Larkin, C., Leech, V., Line, A., Lord, A., Macleod, A., Mooney, P. J., Moule, S., Martin, D. M., Morgan, G. W., Mungall, K., Norbertczak, H., Ormond, D., Pai, G., Peacock, C. S., Peterson, J., Quail, M. A., Rabbinowitsch, E., Rajandream, M. A., Reitter, C., Salzberg, S. L., Sanders, M., Schobel, S., Sharp, S., Simmonds, M., Simpson, A. J., Tallon, L., Turner, C. M., Tait, A., Tivey, A. R., Van Aken, S., Walker, D., Wanless, D., Wang, S., White, B., White, O., Whitehead, S., Woodward, J., Wortman, J., Adams, M. D., Embley, T. M., Gull, K., Ullu, E., Barry, J. D., Fairlamb, A. H., Opperdoes, F., Barrell, B. G., Donelson, J. E., Hall, N., Fraser, C. M., Melville, S. E., and El-Sayed, N. M. (2005) Science 309, 416-422
43. Coppens, I., and Courtoy, P. J. (2000) Annu. Rev. Microbiol. 54, 129-156
44. Vanden Bossche, H., Koymans, L., and Moereels, H. (1995) Pharmacol. Ther. 67, 79-100
45. Roberts, C. W., McLeod, R., Rice, D. W., Ginger, M., Chance, M. L., and Goad, L. J. (2003) Mol. Biochem. Parasitol. 126, 129-142
46. Zhou, W., Cross, G. A., and Nes, W. D. (2007) J. Lipid Res. 48, 665-673
47. Goodpasture, H. C., Hershberger, R. E., and Barnett, A. M., Peterie, J. D. (1985) Arch. Intern. Med. 145, 879-880
48. Leoni, V., Lütjohann, D., and Masterman, T. (2005) J. Lipid Res. 46, 191-195