Structure-based drug design targeting biosynthesis of isoprenoids: A crystallographic state of the art of the involved enzymes

Current Protein and Peptide Science

Volumn 9, Issue 2, 2008, Pages 117-137

  de Ruyck, Jerome ^a   Wouters, Johan ^a  

^a UNIVERSITY OF NAMUR   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXY DEXTRO XYLULOSE 5 PHOSPHATEREDUCTOISOMERASE; 2 C METHYL DEXTRO ERYTHRITOL 2,4 CYCLODIPHOSPHATE SYNTHASE; 3 HYDROXY 3 METHYLGLUTARYL COENZYME A; 4 DIPHOSPHOCYTIDYL 2 C METHYL DEXTRO ERYTHRITOL KINASE; 4 DIPHOSPHOCYTIDYL 2 C METHYL DEXTRO ERYTHRITOL SYNTHASE; ACETYL COENZYME A; ALENDRONIC ACID; ANTIINFECTIVE AGENT; ANTIMALARIAL AGENT; ANTINEOPLASTIC AGENT; BISPHOSPHONIC ACID DERIVATIVE; CHOLESTEROL; CLINDAMYCIN; FARNESYL TRANS TRANSFERASE; FOSMIDOMYCIN; GERANYLTRANSFERASE; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; HYPOCHOLESTEROLEMIC AGENT; ISOMERASE; ISOPENTENYL DIPHOSPHATE; ISOPENTENYL DIPHOSPHATE DELTA ISOMERASE; ISOPRENOID; MEVALONIC ACID; NATURAL PRODUCT; PHOSPHOTRANSFERASE; PROTEIN FARNESYLTRANSFERASE INHIBITOR; SYNTHETASE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ZOLEDRONIC ACID;

CARDIOVASCULAR DISEASE; CATALYSIS; CLINICAL TRIAL; CRYSTALLOGRAPHY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME PHOSPHORYLATION; ENZYMOLOGY; GENOMICS; HELICOBACTER PYLORI; HUMAN; HYPERCHOLESTEROLEMIA; MALARIA; MALIGNANT NEOPLASTIC DISEASE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; OSTEOLYSIS; OSTEOPOROSIS; PLASMODIUM FALCIPARUM; PRENYLATION; REVIEW;

ACYL COENZYME A; ANIMALS; BACTERIA; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; ENZYME INHIBITORS; ENZYMES; FUNGI; HEMITERPENES; HUMANS; MEVALONIC ACID; ORGANOPHOSPHORUS COMPOUNDS; PLANTS; TERPENES;

BACTERIA (MICROORGANISMS); HELICOBACTER PYLORI; MYCOBACTERIUM TUBERCULOSIS; PLASMODIUM FALCIPARUM;

EID: 42049122363     PISSN: 13892037     EISSN: None     Source Type: Journal    
DOI: 10.2174/138920308783955261     Document Type: Review

References (192)

1. Frere, J.M. (1995) Mol. Microbiol., 16, 335-395.
2. Andersson, D.I. (2003) Curr. Opin. Microbiol., 6, 452-456
3. Franceschi, F., Kanyo, Z., Sherer, E.C., and Sutcliffe, J. (2004) Curr. Drug Targets Infect. Disord., 4, 177-191.
4. Walsh, F.M. and Amyes, S.G. (2004) Curr. Opin. Microbiol., 7, 439-444.
5. Sacchettini, J.C. and Poutter, C.D. (1997) Science, 277, 1788-1789.
6. Cane, D.E. (1999) In Comprehensive Natural Products Chemistry, (Barton, D. and Nakanishi, K. Eds,) Elsevier, Oxford.
7. McTaggart, S.J. (2006) Cell Mol. Life Sci., 63, 255-267.
8. Konstantinopoulos, P.A., Karamouzis, M.V. and Papavassiliou, A.G. (2007) Nat. Rev. Drug Discov., 6, 541-555.
9. Zhou, D. and White, R.H. (1991) Biochem. J., 273, 627-634.
10. Rohmer, M., Knani, M., Simonin, P., Sutter, B. and Sahm, H. (1993) Biochem. J., 295 (Pt 2), 517-524.
11. Watanabe, Y., Ito, T., Shiomi, M., Tsujita, Y., Kuroda, M., Arai, M., Fukami, M. and Tamura, A. (1988) Biochim. Biophys. Acta, 960, 294-302.
12. Rohmer, M. (1999) Nat. Prod. Rep., 16, 565-574.
13. Schwarz, M. and Arigoni, D. (1999) In Comprehensive Natural Product Chemistry, (Cane, D. Ed.) Pergamon, Oxford.
14. Sprenger, G.A., Schorken, U., Wiegert, T., Grolle, S., de Graaf A.A., Taylor, S.V., Begley, T.P., Bringer-Meyer, S. and Sahm, H. (1997) Proc. Natl. Acad. Sci. USA, 94, 12857-12862.
15. Lois, L.M., Campos, N., Putra, S.R., Danielsen. K., Rohmer, M. and Boronat, A. (1998) Proc. Natl. Acad. Sci. USA, 95, 2105-2110.
16. Takahashi, S., Kuzuyama, T., Watanabe, H. and Seto, H, (1998) Proc. Natl. Acad. Sci. USA, 95, 9879-9884.
17. Fox, D.T. and Poulter, C.D. (2005) J. Org. Chem., 70, 1978-1985.
18. Rohdich, F., Wungsintaweckul, J., Fellermeier, M., Sagner, S., Herz,. S., Kis, K., Eisenreich, W.. Bacher, A. and Zenk, M.H. (1999) Proc. Natl. Acad. Sci. USA, 96, 11758-11763.
19. Luttgen, H., Rohdich, F., Herz, S., Wungsintaweekul, J., Hecht, S., Schuhr, C.A., Fellermeier, M., Sagner, S., Zenk, M.H., Bacher, A. and Eisenreich, W. (2000) Proc. Natl. Acad Sci. USA, 97, 1062-1067.
20. Herz, S., Wungsintaweekul, J., Schuhr, C.A., Hecht, S., Luttgen, H., Sagner, S., Fellermeier, M., Eisenreich, W., Zenk, M.H., Bacher, A. and Rohdich, F. (2000) Proc. Natl. Acad. Sci. USA, 97, 2496-2490.
21. Takagi, M., Kuzuyama, T., Kaneda, K., Dairi, T. and Seto, H. (2000) Tetrahedron Lett., 41, 3395-3398.
22. Hecht, S., Eisenreich, W., Adam, P., Arnslinger, S., Kis, K., Bacher, A., Arigoni, D. and Rohdich, F. (2001) Proc. Natl. Acad. Sci. USA, 98, 14837-14842.
23. Kollas, A.K., Duin, E.C., Eberl, M., Altincicek, B., Hintz, M., Reichenberg, A., Henschker, D., Henne, A., Steinbrecher, I., Ostrovsky, D.N., Hedderich, R., Beck, E., Jomaa, H. and Wiesner, J. (2002) FEBS Lett., 532, 432-436.
24. Seemann, M., Bui, B.T., Wolff, M., Tritsch, D., Campos, N., Boronat, A., Marquet, A. and Rohmer, M. (2002) Angew Chem. Int. Ed. Engl., 41, 4337-4339.
25. Altincicek, B., Duib, E.C., Reichenberg, A., Hedderich, R., Kollas, A.K., Hintz, M., Wagner, S., Wiesner, J., Beek, E. and Jornaa, H. (2002) FEBS Lett., 532, 437-440.
26. Rohdich, F., Hecht, S., Gartner, K., Adam, P., Krieger, C., Amslinger, S., Arigoni, D., Bacher, A. and Eisenreich, W. (2002) Proc. Natl. Acad. Sci. USA, 99, 1158-1163.
27. Wolff, M., Seemann, M., Tse, Sum Bui, B., Frapart, Y., Tritsch, D., Garcia Estrabot, A., Rodriguez-Concepcion, M., Boronat, A., Marquet, A. and Rohmer, M. (2003) FEBS Lett., 541, 115-120.
28. Eisenreich, W., Bacher, A., Arigoni, D. and Rohdich, F. (2004) Cell Mol. Life Sci., 61, 1401-1426.
29. Laupitz, R., Hecht, S., Arnslinger, S., Zcpeck, F., Kaiser, J., Richter, G., Schramek, N., Steinbacher, S., Huber, R., Arigoni, D., Bacher, A., Eisenreich, W. and Rohdich, F. (2004) Eur. J. Biochem., 271, 2658-2669.
30. Agranoff, B.W., Eggerer, H., Henning, U. and Lynen, F. (1960) J. Biol. Chem., 235, 326-332.
31. Ramos-Valdivia, A.C., van der Heijden, R., Verpoorte, R. and Camara, B. (1997) Eur. J. Biochem., 249, 161-170.
32. Carrigan, C.N. and Poulter, C.D. (2003) J. Am. Chem. Soc., 125, 9008-9009.
33. Lee, S. and Poulter, C.D. (2006) J. Am. Chem. Soc., 128, 11545- 11550.
34. Kaneda, K., Kuzuyama, T., Takagi, M., Hayakawa, Y. and Seto, H. (2001) Proc. Natl. Acad. Sci. USA, 98, 932-937.
35. Barkley, S.J., Cornish, R.M. and Poulter, C.D. (2004) J. Bacteriol., 186, 1911-1817.
36. Takagi, M., Kaneda, K., Shimizu, T., Hayakawa, Y., Seto, II. and Kuzuyama, T. (2004) Biosci. Biotechnol. Biochem., 68, 132-137.
37. Yamashita, S., Hemmi, H., Ikeda, Y., Nakayama, T. and Nishino, T. (2004) Eur. J. Biochem., 271, 1087-1093.
38. Siddiqui, M.A., Yamanaka, A., Hirooka, K., Bamaba, T., Kobayashi, A., Imanaka, T., Fukusaki, E. and Fujiwara, S. (2005) Biochem. Biophys. Res. Commun., 331, 1127-1136.
39. Hoshino, T., Tamegai, H., Kakinuma, K. and Eguchi, T. (2006) Bioorg. Med. Chem., 14, 6555-6559.
40. Johnston, J.B., Walker, J.R., Rothman, S.C. and Poulter, C.D. (2007) J Am. Chem. Soc. 129, 7740-7741.
41. Rothman, S.C., Helm, T.R. and Poulter, C.D. (2007) Biochemistry, 46, 5437-5445.
42. Poulter, C.D. (1978) Acc. Chem. Res., 11, 307-313.
43. Beytia, E., Qureshi, A.A. and Porter, J.W. (1973) J. Biol. Chem., 248, 1856-1867.
44. Campobasso, N., Patel, M., Wilding, I.E., Kallender, H., Rosenberg, M. and Gwynn, M.N. (2004) J. Biol. Chem., 279, 44883-44998.
45. Theisen, M.J., Misra, I., Saadat, D., Campobasso, N., Miziorko, H.M. and Harrison, D.H. (2004) Proc. Natl. Acad. Sci. USA, 101, 16442-16447.
46. Steussy, C.N., Vartia, A.A., Burgner, J.W., 2nd, Suthertin, A., Rodwell, V.W. and Stauffacher, C.V. (2005) Biochemistry, 44, 14256-14267.
47. Pojer, F., Ferrer, J.L., Richard, S.B., Nagegowda, D.A., Chye, M.L., Bach, T.J. and Noel, J.P. (2006) Proc. Natl. Acad. Sci. USA, 103, 11491-11496.
48. Tabernero, L., Bochar, D.A., Rodwell, V.W. and Stauffacher, C.V. (1999) Proc. Natl. Acad. Sci. USA, 96, 7167-7171.
49. Istvan, E.S., Palnitkar, M., Buchanan, S.K. and Deisenbofer, J. (2000) EMBO J., 19, 819-830.
50. Istvan, E.S. and Deisenhofer, J. (2001) Science, 292, 1160-1164.
51. Yang, D., Shipman, L.W., Roessner, CA., Scott, A.I. and Sacchettini, J.C. (2002) J. Biol. Chem., 277, 9462-9467.
52. Fu, Z., Wang, M., Potter, D., Miziorko, H.M. and Kim, J.J. (2002) J. Biol. Chem., 277, 18134-18142.
53. Romanowski, M.J., Bonanno, J.B. and Burley, S.K. (2002) Proteins, 47, 568-571.
54. Kandutsch, A.A., Paulus, H., Levin, E. and Bloch, K. (1964) J. Biol. Chem., 239, 2507-2515,
55. Vaughan, C.J. and Gotto, A.M., Jr. (2004) Circulation, 110, 886-892.
56. Lange, B.M., Rujan, T., Martin, W. and Croteau, R. (2000) Proc. Natl. Acad. Sci. USA, 97, 13172-13177.
57. Lawrence, C.M., Rodwell, V.W. and Stauffacher, C.V. (1995) Science, 268, 1758-1762.
58. Istvan, E.S. and Deisenhofer,J. (2000) Biochim. Biophys. Acta, 1529, 9-18.
59. Huang, K.X., Scott, A.I. and Bennett, G.N. (1999) Protein Expr. Purif., 17, 33-40.
60. Rohmer, M., Grosdemange-Billiard, C., Seemann, M. and Tritsch, D. (2004) Curr. Opin. Investig. Drugs, 5, 154-162.
61. Rohdich, F., Bacher, A. and Eisenreich, W. (2005) Biochem. Soc. Trans., 33, 785-791.
62. Badger, J., Sauder, J.M., Adams, J.M., Antonysamy, S., Bain, K., Bergseid, M.G., Buchanan, S.G., Buchanan, M.D., Batiyenko, Y., Christopher, J.A., Emtage, S., Eroshkina, A., Feil, I., Furlong, E.B., Gajiwala, K.S., Gao, X., He, D., Hendle, J., Huber, A., Hoda, K., Kearins, P., Kissinger, C., Laubert, B., Lewis, H.A., Lin, J., Loomis, K., Lorimer, D., Louie, G., Maletic, M., Marsh, C.D., Miller, I., Molinari, J., Muller-Dieckmann, H.J., Newman, J.M., Noland, B.W., Pagarigan, B., Park, F., Peat, T.S., Post, K.W., Radojicic, S., Ramos, A., Romero, R., Rutter, M.E., Sanderson, W.E., Schwinn, K.D., Tresser, J., Winhoven, J., Wright, T.A., Wu, L., Xu, J. and Harris, T.J. (2005) Proteins, 60, 787-796.
63. Hunter, W.N. (2007) J. Biol. Chem., 282, 21573-21577.
64. Xiang, S., Usunow, G., Lange, G., Busch, M. and Tong, L. (2007) J. Biol. Chem., 282, 2676-2682.
65. Proteau, P.J. (2004) Bioorg. Chem., 32, 483-493.
66. Ricagno, S., Grolle, S., Bringer-Meyer, S., Sahm, H., Lindqvist, Y. and Schneider, G. (2004) Biochim. Biophys. Acta, 1698, 37-44.
67. Reuter, K., Sanderbrand, S., Joroaa, H., Wiesner, J., Steinbrecher, I., Beck, E., Hintz, M., Klebe, G. and Stubbs, M.T. (2002) J. Biol. Chem., 277, 5378-5384.
68. Yajima, S., Nonaka, T., Kuzuyama, T., Seto, H. and Ohsawa, K. (2002) J. Biochem. (Tokyo), 131, 313-317.
69. Steinbacher, S., Kaiser, J., Eisenreich, W., Huber, R., Bacher, A. and Rohdich, F. (2003) J. Biol. Chem., 278, 18401-18407.
70. Yajima, S., Hara, K., Sanders, J.M., Yin, F., Ohsawa, K., Wiesner, J., Jomaa, H. and Oldfield, E. (2004) J. Am. Chem. Soc., 126, 10824-10825.
71. Mac Sweeney, A., Lange, R., Fernandes, R.P., Schulz, H., Dale, G.E., Douangamath, A., Proteau, P.J. and Oefner, C. (2005) J. Mol. Biol., 345, 115-127.
72. Yajima, S., Hara, K., Lino, D., Sasaki, Y., Kuzuyama, T., Ohsawa, K. and Seto, H. (2007) Acta Crystallogr, F. Struct. Biol. Cryst. Commun, 63, 466-470.
73. Henriksson, L.M., Bjorkelid, C., Mowbray, S.L. and Unge, T. (2006) Acta Crystallogr. D. Biol. Crystallogr., 62, 807-813.
74. Richard, S.B., Bowman, M.E., Kwiatkowski, W., Kang, I., Chow, C., Lillo, A.M., Cane, D.E. and Noel, J.P. (2001) Nat. Struct. Biol., 8, 641-648.
75. Kemp, L.E., Bond, C.S. and Hunter, W.N. (2003) Acta Crystallogr. D. Biol. Crystallogr., 59, 607-610.
76. Gabrielsen, M., Kaiser, J., Rohdich, F., Eisenreich, W., Laupitz, R., Bacher, A., Bond, C.S. and Hunter, W.N. (2006) FEBS J., 273, 1065-1073.
77. Miallau, L., Alphey, M.S., Kemp, L.E., Leonard, G.A., McSweeney, S.M., Hecht, S., Bacher, A., Eisenreich, W., Rohdich, F. and Hunter, W.N. (2003) Proc. Natl. Acad. Sci. USA, 100, 9173-9178.
78. Wada, T., Kuzuyama, T., Satoh, S., Kuramitsu, S., Yokoyama, S., Unzai, S., Tame, J.R. and Park, S.Y. (2003) J. Biol. Chem., 278, 30022-30027.
79. Richard, S.B., Ferrer, J.L., Bowman, M.E., Lillo, A.M., Tetzlaff, C.N., Cane, D.E. and Noel, J.P. (2002) J. Biol. Chem., 277, 8667-8672.
80. Steinbacher, S., Kaiser, J., Wungsintaweekul, J., Hecht, S., Eisenreich, W., Gerhardt, S., Bacher, A. and Rohdich, F. (2002) J. Mol. Biol., 316, 79-88.
81. Kemp, L.E., Bond, C.S. and Hunter, W.N. (2002) Proc. Natl. Acad. Sci. USA, 99, 6591-6596.
82. Kemp, L.E., Alphey, M.S., Bond, C.S., Ferguson, M.A., Hecht, S., Bacher, A., Eisenreich, W., Rohdich, F. and Hunter, W.N. (2005) Acta Crystallogr. D. Biol. Crystallogr., 61, 45-52.
83. Sgraja, T., Kemp, L.E., Ramsden, N. and Hunter, W.N. (2005) Acta Crystallogr. Sect. F. Struct. Biol. Cryst. Commun., 61, 625-629.
84. Crane, C.M., Kaiser, J., Ramsden, N.L., Lauw, S., Rohdich, F., Eisenreich, W., Hunter, W.N., Bacher, A. and Diederich, F. (2006) Angew. Chem. Int. Ed. Engl., 45, 1069-1074.
85. Lehmann, C., Lim, K., Toedt, J., Krajewski, W., Howard, A., Eisenstein, E. and Herzberg, O. (2002) Proteins, 49, 135-138.
86. Kishida, H., Wada, T., Unzai, S., Kuzuyama, T., Takagi, M., Terada, T., Shirouzu, M., Yokoyama, S., Tame, J.R. and Park, S.Y. (2003) Acta Crystallogr. D. Biol. Crystallogr., 59, 23-31.
87. Ni, S., Robinson, H., Marsing, G.C., Bussiere, D.E. and Kennedy, M.A. (2004) Acta Crystallogr. D. Biol. Crystallogr., 60, 1949-1957.
88. Richard, S.B., Lillo, A.M., Tetzlaff C.N., Bowman, M.E., Noel, J.P. and Cane, D.E. (2004) Biochemistry, 43, 12189-12197.
89. Rohdich, F., Wungsintaweekul, J., Luttgen, H., Fischer, M., Eisenreich, W., Schuhr, C.A., Fellermeier, M., Schramek, N., Zenk, M.H. and Bacher, A. (2000) Proc. Natl. Acad. Sci. USA, 97, 8251-8256.
90. Gabrielsen, M., Bond, C.S., Hallyburton, I., Hecht, S., Bacher, A., Eisenreich, W., Rohdich, F. and Hunter, W.N. (2004) J. Biol. Chem., 279, 52753-52761.
91. Wang, K.C. and Ohnuma, S. (2000) Biochim. Biophys. Acta, 1529, 33-48.
92. Durbecq, V., Sainz, G., Oudjama, Y., Clantin, B., Bompard-Gilles, C., Tricot, C., Caillet, J., Stalon, V., Droogmans, L. and Villeret, V. (2001) EMBO J., 20, 1530-1537.
93. Bonanno, J.B., Edo, C., Eswar, N., Pieper, U., Romanowski, M.J., Ilyin, V., Gerchman, S.E., Kycia, H., Studier, F.W., Sali, A. and Burley, S.K. (2001) Proc. Natl. Acad Sci. USA, 98, 12896-12901.
94. Wouters, J., Oudjama, Y., Barkley, S.J., Tricot, C., Stalon, V., Droogmans, L. and Poulter, C.D. (2003) J. Biol. Chem., 278, 11903-11908.
95. Wouters, J., Oudjama, Y., Ghosh, S., Stalon, V., Droogmans, L. ana Oldfield, E. (2003) J. Am. Chem. Soc., 125, 3198-3199.
96. Wouters, J., Oudjama, Y., Stalon, V., Droogmans, L. and Poulter, C.D. (2004) Proteins, 54, 216-221.
97. Wouters, J., Yin, F., Song, Y., Zhang, Y., Oudjama, Y., Stalon, V., Droogmans, L., Morita, C.T. and Oldfield, E. (2005) J. Am. Chem. Soc., 127, 536-537.
98. de Ruyck, J., Durisotti, V., Oudjama, Y. and Wouters, J. (2006) J. Biol. Chem., 281, 17864-17869.
99. Zheng, W., Sun, F., Bartlam, M., Li, X., Li, R. and Rao, Z. (2007) J. Mol. Biol., 366, 1447-1458.
100. Steinbacher, S., Kaiser, J., Gerhardt, S., Eisenreich, W., Huber, R., Bacher, A. and Rohdich, F. (2003) J. Mol. Biol., 329, 973-982.
101. Tarshis, L,C., Yan, M., Poulter, C.D. and Sacchettini, J.C. (1994) Biochemistry, 33, 10871-10877.
102. Tarshis, L.C., Proteau, P.J., Kellogg, B.A., Sacchettini, J.C. and Poulter, C.D. (1996) Proc. Natl. Acad. Sci. USA, 93, 15018-15023.
103. Kavanagh, K.L., Guo, K., Dunford, J.E., Wu, X., Knapp, S., Ebetino, F.H., Rogers, M.J., Russell, R.G. and Oppermann, U. (2006) Proc. Natl. Acad Sci. USA, 103, 7829-7834.
104. Rondeau, J.M., Bitsch, F., Bourgier, E., Geiser, M., Hemmig, R., Kroemer, M., Lehmann, S., Ramage, P., Rieffel, S., Strauss, A., Green, JR. and Jahnkc, W. (2006) Chem. Med Chem., 1, 267-273.
105. Hosfield, D.J., Zhang, Y., Dougan, D.R., Broun, A., Tari, L.W., Swanson, R.V. and Finn, J. (2004) J. Biol. Chem., 279, 8526-8529.
106. Gabelli, S.B., McLellan, J.S., Montalvetti, A., Oldfield, E., Docampo, R. and Amzel, L.M. (2006) Proteins, 62, 80-88.
107. Mao, J., Mukherjee, S., Zhang, Y., Cao, R., Sanders, J.M., Song, Y., Zhang, Y., Meints, G.A., Gao, Y.G., Mukkamala, D., Hudock, M.P. and Oldfield, E. (2006) J. Am. Chem. Soc., 128, 14485-14497.
108. Kloer, D.P., Welsch, R., Beyer, P. and Schutz, G.E. (2006) Biochemistry, 45, 15197-15204.
109. Chang, TH., Guo, R.T., Ko, T.P., Wang, A.H. and Liang, P.H. (2006) J. Biol. Chem., 281, 14991-15000.
110. Kavanagh, K.L., Dunford, J.E., Bunkoczi, G., Russell, R.G. and Oppermann, U. (2006) J. Biol. Chem., 281, 22004-22012.
111. Zhang, C., Liu, L., Xu, H., Wei, Z., Wang, Y., Lin, Y. and Gong, W. (2007) J. Mol. Biol., 366, 1437-1446.
112. Nagano,N., Orengo, C.A. and Thomton, J.M. (2002) J. Mol. Biol., 321, 741-765.
113. de Ruyck, J., Rothman, S.C., Poulter, C.D. and Wouters, J. (2005) Biochem. Biophyg. Res. Commun., 338,1515-1519.
114. Breitling, R., Laubner, D., Clizbe, D., Adamski, J. and Krisans, S.K. (2003) J. Mol. Evol., 57, 282-291.
115. Clizbe, D.B., Owens, M.L., Masuda, K.R., Shackelford, J.E. and Krisans, S.K. (2007) J. Biol. Chem., 282, 6668-6676.
116. Poulter, C.D., Satterwhite, D.M. and Rilling, H.C. (1976) J. Am. Chem. Soc., 98, 3376-3377.
117. Sanchez, V.M., Crespo, A., Gutkind, J.S. and Tudanski, A.G. (2006) J. Phys. Chem. B. Condens. Matter. Mater. Surf Interfaces Biophys., 110, 18052-18057.
118. Mao, J., Gao, Y.G., Odch, S., Robinson, H., Montalvetti, A., Docampo, R. and Oldfield, E. (2004) Acta. Crystallogr. D. Biol. Crystallogr., 60, 1863-1866.
119. Quondam, M., Barbato, C., Pickford, A., Helmer-Citterich, M. and Macino, G. (1997) Protein Eng., 10, 1047-1055.
120. Nishio, K., Nodake, Y., Hamada, K., Suto, K., Nakagawa, N., Kuramitsu, S. and Miura, K. (2004) Acta Crystallogr. D. Biol. Crystallogr., 60, 178-180.
121. Hemmi, H., Noike, M., Nakayama, T. and Nishino, T. (2003) Eur. J. Biochem., 270, 2186-2194.
122. Liang, P.H., Ko, T.P. and Wang, A.H. (2002) Eur. J. Biochem., 269, 3339-3354.
123. Szkopinska, A. and Plochocka, D. (2005) Acta Biochim. Pol., 52, 45-55.
124. Sorensen, T.L., McAuley, K.E., Flaig, R. and Duke, E.M. (2006) Trends Biotechnol., 24, 500-508.
125. Ren, J. and Stammers, D.K. (2005) Trends Pharmacol. Sci., 26, 4-7.
126. Garman, E. and Laver, G. (2004) Curr. Drug Targets, 5, 119-136.
127. Poynter, J.N., Gruber, S.B., Higgins, P.D.; Almog, R., Bonner, J.D., Rennert, H.S., Low, M., Greenson, J.K. and Rennert, G. (2005) N. Engl. J. Med., 352, 2184-2192.
128. Brown, A.J. (2007) Clin. Exp. Pharmacol. Physiol., 34, 135-141.
129. Ghittoni, R., Patrussi, L., Pirozzi, K., Pellegrini, M., Lazzerini, P.E., Capecchi, P.L., Pasini, F.L. and Baldari, C.T. (2005) FASEB J., 19, 605-607.
130. Crisby, M., Nordin-Fredriksson, G., Shah, D.K., Yano, J., Zhu, J. and Nilsson, J. (2001) Circulation, 103, 926-933.
131. Cole, S.L. and Vassar, R. (2006) Neurobiol. Dis., 22, 209-222.
132. Buhaescu, I. and Izzedine, H. (2007) Clin. Biochem., 40, 575-584.
133. Waterham, H.R. (2006) FEBS Lett., 580, 5442-5449.
134. Pandit, J., Danley, D.E., Schulte, G.K., Mazzalupo, S., Pauly, T.A., Hayward, C.M., Hamanaka, E.S., Thompson, J.F. and Harwood, H.J., Jr. (2000) J. Biol. Chem., 275, 30610-30617.
135. Ezzati, M., Hoorn, S.V., Rodgers, A., Lopez, A.D., Mathers, C.D. and Murray, C.J. (2003) Lancet, 362, 271-280.
136. Endo, A., Kuroda, M. and Tanzawa, K. (1976) FEBS Lett., 72, 323-326.
137. Zhang, Q.Y., Wan, J., Xu, X., Yang, G.F. Ren, Y.L., Liu, J.J., Wang, H. and Guo, Y. (2007) J. Comb. Chem., 9, 131-138.
138. Charlton-Menys, V. and Durrington, P.N. (2007) Drugs, 67, 11-16.
139. Rodriguez-Concepcion, M. (2004) Curr. Pharm. Des., 10, 2391-2400.
140. Carlson, J.C., Byrd, B.D. and Omlin, F.X. (2004) BMC Public Health, 4, 33.
141. Kreier, J.P. (1980) In Malaria: Epidemiology, Chemotherapy, Morphology, and Metabolism, Academic Press Inc., New York.
142. Hviid, L. (1998) Expert Rev. Mol. Med., 1998, 1-10.
143. Woodrow, C.J. and Krishna, S. (2006) Cell Mol. Life Sci., 63, 1586-1596.
144. Jomaa, H., Wiesner, J., Sanderbrand, S., Altincicek, B., Wcidemeyer, C., Hintz, M., Turbachova, I., Eberl, M., Zeidler, J., Lichtenthaler, H.K., Soldati, D. and Beck, E. (1999) Science, 285, 1573-1576.
145. Kuzuyama, T., Shimizu, T., Takahashi, S. and Seto, H. (1998) Tetrahedron Lett., 39, 7913-7916.
146. Okuhara, M., Kuroda, Y., Goto, T., Okamoto, M., Terano, H., Kohsaka, M., Aoki, H. and Imanaka, H. (1980) J. Antibiot. (Tokyo), 33, 24-28.
147. Singh, N., Cheve, G., Avery, M.A. and McCurdy, C.R. (2007) Curr. Pharm. Des., 13, 1161-1177.
148. Borrmann, S., Lundgren, I., Oyakhirome, S.; Impouma, B., Matsiegui, P.B., Adegnika, A.k, Issifou, S., Kun, J.F., Hutchinson, D., Wiesner, J., Jomaa, H. and Kremsner, P.G. (2006) Antimicrob. Agents Chemother., 50, 2713-2718.
149. Burkhardt, D., Wiesner, J., Stoesser, N., Ramharter, M., Uhlemann, A.C., Issifou, S., Jomaa, H., Krishna, S., Kremsner, P.J. and Borrmann, S. (2007) Int. J. Parasitol., 37, 777-785.
150. Silber, K., Heidler, P., Kurz, T. and Klebe, G. (2005) J. Med. Chem., 48, 13547-3563.
151. Singh, N., Cheve, G., Avery, M.A. and McCurdy, C.R. (2006) J. Chem. Inf. Model., 46, 1360-1370.
152. Wiesner, J., Henschker, D., Hutchinson, D.B., Beck, E. and Jomaa, H. (2002) Antimicrob. Agents Chemother., 46, 2889-2894.
153. Wiesner, J., Borrmann, S. and Jomaa, H. (2003) Parasitol. Res., 90 Suppl 2, S71-76.
154. Illarionova, V., Kaiser, J., Ostrozhenkova, E., Bacher, A., Fischer, M., Eisenreich, W. and Rohdich, F. (2006) J. Org. Chem., 71, 8824-8834.
155. Hirsch, A.K., Lauw, S., Gersbach, P., Schweizer, W.B., Rohdich, F., Eisenreich, W., Bacher, A. and Diederich, F. (2007) Chem. Med. Chem., 2, 806-810.
156. Lane, K.T. and Beese, L.S. (2006) J. Lipid Res., 47, 681-699.
157. Melton, L.J. (1988) In Osteoporosis: Etiology, Diagnosis, Management, (Riggs, B.L. and Melton, L.J. Eds.) pp. 133-154, Raven Press, New York.
158. Clark, E.A., King, W.G., Brugge, J.S., Symons, M. and Hynes, R.O. (1998) J. Cell Biol., 142, 573-586.
159. Delmas, P.D. (2002) Lancet, 359, 2018-2026.
160. Langston, A.L. and Ralston, S.H. (2004) Rheumatology (Oxford), 43, 955-959.
161. Berenson, J.R. (2002) Semin. Oncol., 29, 12-18.
162. Coleman, R.E. (2004) Oncologist, 9 Suppl 4, 14-27.
163. van Beek, E., Pieterman, E., Cohen, L., Lowik, C. and Papapoulos, S. (1999) Biochem. Biophys. Res. Commun., 255, 491-494.
164. van Beek, E., Pieterman, E., Cohen, L., Lowik, C. and Papapoulos, S. (1999) Biochem. Biophys. Res. Commun., 264, 108-111.
165. Bergstrom, J.D., Bostedor, R.G., Masarachia, P.J., Reszka, A.A. and Rodan, G. (2000) Arch. Biochem. Biophys., 373, 231-241.
166. Dunford, J.E., Thompson, K., Coxon, F.P., Luckman, S.P., Hahn, F.M., Poulter, C.D., Ebetino, F.H. and Rogers, M.J. (2001) J. Pharmacol. Exp. Ther., 296, 235-242.
167. Martin, M.B., Arnold, W., Heath, H.T., 3rd, Urbina, J.A. and Oldfield, E. (1999) Biochem. Biophys. Res. Commun., 263, 754-758.
168. Reszka, A.A. and Rodan, G.A. (2004) Mini Rev. Med. Chem., 4, 711-719.
169. Goffinet, M., Thoulouzan, M., Pradines, A., Lajoic-Mazene, I., Weinbaum, C., Faye, J.C. and Seronie-Vivien, S. ((2006) BMC Cancer, 6, 60.
170. Szabo, C.M., Matsumura, Y., Fukura, S., Martin, M.B., Sanders, J.M., Sengupta, S., Cieslak, J.A., Loftus, T.C., Lea, C.R., Lee, H.J., Koohang, A., Coates, R.M., Sagami, H. and Oldfield, E. (2002) J. Med Chem., 45, 2185-2196.
171. Guo, R.T., Cao, R., Liang, P.H., Ko, T.P., Chang, T,H., Hudock, M.P., Jeng, W.Y., Chen, C.K., Zhang, Y., Song, Y., Kuo, C.J., Yin, F., Oldfield, E. and Wang, A.H. (2007) Proc. Natl. Acad. Sci. USA.
172. Stewart, B.W. and Kleihues, P. (2003) In World health organization international agency for research on cancer, IARCPress, Lyon, France.
173. Tamanoi, F. and Sigman, D.S. (2001) in The Enzymes, Academic press, San Diego, CA.
174. Pechlivanis, M. and Kuhlmann, J. (2006) Biochim. Biophys. Acta, 1764, 1914-1931.
175. Yokoyama, K., Goodwin, G.W., Ghomashchi, F., Glomset, J. and Gelb, M.H. (1992) Biochem. Soc. Trans., 20, 489-494.
176. Casey, P.J. and Seabra, M.C. (1996) J. Biol. Chem., 271, 5289-5292.
177. Zhang, H., Seabra, M.C. and Deisenhofer, 1 (2000) Structure, J, 241-251.
178. Long, S.B., Casey, P.J. and Beese, L.S. (2002) Nature, 419, 645-650.
179. Taylor, J.S. Reid, T.S., Terry, K.L., Casey, P.J. and Beese, L.S. (2003) Embo. J., 22, 5963-5974.
180. Hicks, K.A., Hartman, H.L. and Fierke, C.A. (2005) Biochemistry, 44, 15325-15333.
181. Seabra, M.C., Reiss, Y., Casey, P.J., Brown, M.S. and Goldstein, J.L. (1991) Cell, 65, 429-434.
182. Furfine, E.S., Leban, J.J., Landavazo, A., Moomaw, J.F. and Casey, P.J. (1995) Biochemistry, 34, 6857-6862.
183. Caponigro, F, Casale, M. and Bryce, J. (2003) Expert Opin. Investig. Drugs, 12, 943-954.
184. Basso, A.D., Kirschmeier, P. and Bishop, W.R. (2006) J. Lipid. Res., 47, 15-31.
185. Gelb, M.H., Brunsveld, L., Hrycyna, C.A., Michaelis, S., Tamanoi, F., Van Voorhis, W.C. and Waldmann, H. (2006) Nat. Chem. Biol., 2, 518-528.
186. Swanson, K.M. and Hohl, R.J. (2006) Curr. Cancer Drug Targets, 6, 15-37.
187. Reiss, Y., Goldstein, J.L., Seabra, M.C., Casey, P.J. and Brown, M. S. (1990) Cell, 62, 81-88.
188. Long, S.B., Haneock, P.J., Kral, A.M., Hellinga, H.W. and Beese, L.S. (2001) Proc. Natl. Acad. Sci. USA, 98, 12948-12953.
189. Taveras, A.G., Kirschmeier, P. and Baum, C.M. (2003) Curr. Top. Med. Chem., 3, 1103-1114.
190. Venet, M., End, D. and Angibaud, P. (2003) Curr. Top. Med. Chem., 3, 1095-1102.
191. Reid, T.S., Long, S.B. and Beese, L.S. (2004) Biochemistry, 43, 9000-9008.
192. DeLano, W.L. (2002) The PyMOL Molecular Graphics System, DeLano Scientific, San Carlos, CA, USA.