Novel inhibitors of Plasmodium falciparum dihydroorotate dehydrogenase with anti-malarial activity in the mouse model

Journal of Biological Chemistry

Volumn 285, Issue 43, 2010, Pages 33054-33064

  Booker, Michael L ^a   Bastos, Cecilia M ^a   Kramer, Martin L ^a   Barker Jr , Robert H ^a   Skerlj, Renato ^a   Sidhu, Amar Bir ^b   Deng, Xiaoyi ⁱ   Celatka, Cassandra ^a   Cortese, Joseph F ^b   Guerrero Bravo, Jose E ^c   Crespo Llado, Keila N ^c   Serrano, Adelfa E ^c   Angulo Barturen, Iñigo ^d   Jiménez Díaz, María Belén ^d   Viera, Sara ^d   Garuti, Helen ^d   Wittlin, Sergio ^e,f   Papastogiannidis, Petros ^e,f   Lin, Jing Wen ^g   Janse, Chris J ^g   Khan, Shahid M ^g   Duraisingh, Manoj ^h   Coleman, Bradley ^h   Goldsmith, Elizabeth J ⁱ   Phillips, Margaret A ⁱ   Munoz, Benito ^b   Wirth, Dyann F ^h   Klinger, Jeffrey D ^a   Wiegand, Roger ^b   Sybertza, Edmund ^a   more..

^a GENZYME CORPORATION   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^c UNIVERSITY OF PUERTO RICO SCHOOL OF MEDICINE   (Puerto Rico)

^d GLAXOSMITHKLINE   (Spain)

^e SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

^f UNIVERSITY OF BASEL   (Switzerland)

^g LEIDEN UNIVERSITY MEDICAL CENTER   (Netherlands)

^h HARVARD SCHOOL OF PUBLIC HEALTH   (United States)

ⁱ UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHETIC PATHWAY; CARBOXAMIDES; CAUSATIVE AGENTS; CLINICAL DEVELOPMENT; HIGH THROUGHPUT; IN-VITRO; MEDICINAL CHEMISTRY; MOUSE MODELS; NANOMOLAR; ORAL EXPOSURE; PARASITE-; PLASMODIUM FALCIPARUM; RATE-LIMITING STEPS; STRUCTURAL DATA; TOXICITY TESTING;

AMINO ACIDS; BINDING ENERGY; BINDING SITES; BIOCHEMISTRY; BIOSYNTHESIS; ENZYME INHIBITION; THIOPHENE; TISSUE CULTURE;

CELL CULTURE;

DIHYDROOROTATE DEHYDROGENASE; DIHYDROOROTATE DEHYDROGENASE INHIBITOR; GENZ 667348; GENZ 668857; GENZ 669178; N ALKYL 5 (1H BENZIMIDAZOL 1 YL)THIOPENE 2 CARBOXAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMALARIAL ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; CYTOLYSIS; DRUG ABSORPTION; DRUG BINDING SITE; DRUG DISTRIBUTION; DRUG EFFICACY; DRUG EXCRETION; DRUG IDENTIFICATION; DRUG METABOLISM; DRUG POTENCY; DRUG TOLERABILITY; ENZYME INHIBITION; ERYTHROCYTE; HIGH THROUGHPUT SCREENING; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MALARIA FALCIPARUM; MAXIMUM PLASMA CONCENTRATION; MOUSE; NONHUMAN; PLASMODIUM BERGHEI; PLASMODIUM BERGHEI INFECTION; PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM VIVAX MALARIA; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ANIMALS; ANTIMALARIALS; CELL LINE; DISEASE MODELS, ANIMAL; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; HUMANS; IMIDAZOLES; MALARIA, FALCIPARUM; MICE; MICE, INBRED NOD; MICE, SCID; OXIDOREDUCTASES ACTING ON CH-CH GROUP DONORS; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PROTOZOAN PROTEINS; RATS;

MURINAE; PLASMODIUM FALCIPARUM;

EID: 77958511348     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M110.162081     Document Type: Article

References (56)

1. Subbayya, I. N., Ray, S. S., Balaram, P., and Balaram, H. (1997) Indian J. Med. Res. 106, 79-94
2. Reyes, P., Rathod, P. K., Sanchez, D. J., Mrema, J. E., Rieckmann, K. H., and Heidrich, H. G. (1982) Mol. Biochem. Parasitol. 5, 275-290
3. Caroline, D. F. (1969) J. Bacteriol. 100, 1371-1377
4. Taylor, M. L., Taylor, W. H., Eames, D. F., and Taylor, C. D. (1971) J. Bacteriol. 105, 1015-1027
5. Williams, J. C., and O'Donovan, G. A. (1973) J. Bacteriol. 115, 1071-1076
6. Jones, M. E. (1980) Annu. Rev. Biochem. 49, 253-279
7. van der Plas, J., Hellingwerf, K. J., Seijen, H. G., Guest, J. R., Weiner, J. H., and Konings, W. N. (1983) J. Bacteriol. 153, 1027-1037
8. Skophammer, R. G., Servin, J. A., Herbold, C. W., and Lake, J. A. (2007) Mol. Biol. Evol. 24, 1761-1768
9. Denis-Duphil, M. (1989) Biochem. Cell Biol. 67, 612-631
10. Jordan, D. B., Bisaha, J. J., and Picollelli, M. A. (2000) Arch. Biochem. Biophys. 378, 84-92
11. Chen, J. J., and Jones, M. E. (1976) Arch. Biochem. Biophys. 176, 82-90
12. Gero, A. M., O'Sullivan, W. J., and Brown, D. J. (1985) Biochem. Med. 34, 60-69
13. Knecht, W., and Löffler, M. (1998) Biochem. Pharmacol. 56, 1259-1264
14. Taylor, W. H., and Taylor, M. L. (1964) J. Bacteriol. 88, 105-110
15. Löffler, M., Jöckel, J., Schuster, G., and Becker, C. (1997) Mol. Cell Biochem. 174, 125-129
16. Eakin, R. T., and Mitchell, H. K. (1969) Arch. Biochem. Biophys. 134, 160-171
17. Kennedy, J. (1973) Arch. Biochem. Biophys. 157, 369-373
18. Miller, R. W., and Curry, J. R. (1969) Can J. Biochem. 47, 725-734
19. Fry, M., and Beesley, J. E. (1991) Parasitology 102, 17-26
20. Painter, H. J., Morrisey, J. M., Mather, M. W., and Vaidya, A. B. (2007) Nature 446, 88-91
21. Liu, S., Neidhardt, E. A., Grossman, T. H., Ocain, T., and Clardy, J. (2000) Structure 8, 25-33
22. Hurt, D. E., Sutton, A. E., and Clardy, J. (2006) Bioorg. Med. Chem. Lett. 16, 1610-1615
23. Deng, X., Gujjar, R., El Mazouni, F., Kaminsky, W., Malmquist, N. A., Goldsmith, E. J., Rathod, P. K., and Phillips, M. A. (2009) J. Biol. Chem. 284, 26999-27009
24. Baldwin, J., Farajallah, A. M., Malmquist, N. A., Rathod, P. K., and Phillips, M. A. (2002) J. Biol. Chem. 277, 41827-41834
25. Patel, V., Booker, M., Kramer, M., Ross, L., Celatka, C. A., Kennedy, L. M., Dvorin, J. D., Duraisingh, M. T., Sliz, P., Wirth, D. F., and Clardy, J. (2008) J. Biol. Chem. 283, 35078-35085
26. Phillips, M. A., Gujjar, R., Malmquist, N. A., White, J., El Mazouni, F., Baldwin, J., and Rathod, P. K. (2008) J. Med. Chem. 51, 3649-3653
27. Gujjar, R., Marwaha, A., El Mazouni, F., White, J., White, K. L., Creason, S., Shackleford, D. M., Baldwin, J., Charman, W. N., Buckner, F. S., Charman, S., Rathod, P. K., and Phillips, M. A. (2009) J. Med. Chem. 52, 1864-1872
28. Otwinowski, Z., and Minor, W. (1997) Methods Enzymol. 276, 307-326
29. McCoy, A. J. (2007) Acta Crystallogr. D Biol. Crystallogr. 63, 32-41
30. Emsley, P., and Cowtan, K. (2004) Acta Crystallogr. D Biol. Crystallogr. 60, 2126-2132
31. Murshudov, G. N., Vagin, A. A., and Dodson, E. J. (1997) Acta Crystallogr. D Biol. Crystallogr. 53, 240-255
32. Cowtan, K. (1998) Acta Crystallogr. D Biol. Crystallogr. 54, 750-756
33. Davis, I. W., Leaver-Fay, A., Chen, V. B., Block, J. N., Kapral, G. J., Wang, X., Murray, L. W., Arendall, W. B., 3rd, Snoeyink, J., Richardson, J. S., and Richardson, D. C. (2007) Nucleic Acids Res. 35, W375-W383, web server issue
34. Kleywegt, G. J., and Jones, T. A. (1994) CCP4/ESF-EACBM Newsletter on Protein Crystallography 31, 9-14
35. Holm, L., and Park, J. (2000) Bioinformatics 16, 566-567
36. Plouffe, D., Brinker, A., McNamara, C., Henson, K., Kato, N., Kuhen, K., Nagle, A., Adrián, F., Matzen, J. T., Anderson, P., Nam, T. G., Gray, N. S., Chatterjee, A., Janes, J., Yan, S. F., Trager, R., Caldwell, J. S., Schultz, P. G., Zhou, Y., and Winzeler, E. A. (2008) Proc. Natl. Acad. Sci. U.S.A. 105, 9059-9064
37. Kocken, C. H., Ozwara, H., van der Wel, A., Beetsma, A. L., Mwenda, J. M., and Thomas, A. W. (2002) Infect. Immun. 70, 655-660
38. Franke-Fayard, B., Djokovic, D., Dooren, M. W., Ramesar, J., Waters, A. P., Falade, M. O., Kranendonk, M., Martinelli, A., Cravo, P., and Janse, C. J. (2008) Int. J. Parasitol. 38, 1651-1662
39. Janse, C. J., and Waters, A. P. (1995) Parasitol. Today 11, 138-143
40. Janse, C. J., Franke-Fayard, B., Mair, G. R., Ramesar, J., Thiel, C., Engelmann, S., Matuschewski, K., van Gemert, G. J., Sauerwein, R. W., and Waters, A. P. (2006) Mol. Biochem. Parasitol. 145, 60-70
41. Kansy, M., Senner, F., and Gubernator, K. (1998) J. Med. Chem. 41, 1007-1010
42. Obach, R. S., Baxter, J. G., Liston, T. E., Silber, B. M., Jones, B. C., MacIntyre, F., Rance, D. J., and Wastall, P. (1997) J. Pharmacol. Exp. Ther. 283, 46-58
43. Sanguinetti, M. C., and Tristani-Firouzi, M. (2006) Nature 440, 463-469
44. Peters, W. (1975) Ann. Trop. Med. Parasitol. 69, 155-171
45. Peters, W. (1987) Chemotherapy and Drug Resistance in Malaria, 2nd Ed., pp. 145-273, Academic Press, Orlando, FL
46. National-Research-Council. (1996) Guide for the Care and Use of Laboratory Animals, National Academy Press, Washington, D. C.
47. Franke-Fayard, B., Trueman, H., Ramesar, J., Mendoza, J., van der Keur, M., van der Linden, R., Sinden, R. E., Waters, A. P., and Janse, C. J. (2004) Mol. Biochem. Parasitol. 137, 23-33
48. Angulo-Barturen, I., Jiménez-Díaz, M. B., Mulet, T., Rullas, J., Herreros, E., Ferrer, S., Jiménez, E., Mendoza, A., Regadera, J., Rosenthal, P. J., Bathurst, I., Pompliano, D. L., Gómez de las Heras, F., and Gargallo-Viola, D. (2008) PLoS ONE 3, e2252
49. Jiménez-Díaz, M. B., Mulet, T., Gómez, V., Viera, S., Alvarez, A., Garuti, H., Vázquez, Y., Fernández, A., Ibáñez, J., Jiménez, M., Gargallo-Viola, D., and Angulo-Barturen, I. (2009) Cytometry A 75, 225-235
50. Hurt, D. E., Widom, J., and Clardy, J. (2006) Acta Crystallogr. D Biol. Crystallogr. 62, 312-323
51. Fairbanks, L. D., Bofill, M., Ruckemann, K., and Simmonds, H. A. (1995) J. Biol. Chem. 270, 29682-29689
52. Hersh, E. V., and Moore, P. A. (2004) J. Am. Dent. Assoc. 135, 298-311
53. Giao, P. T., and de Vries, P. J. (2001) Clin. Pharmacokinet. 40, 343-373
54. Saul, A., Prescott, N., Smith, F., Cheng, Q., and Walliker, D. (1997) Mol. Biochem. Parasitol. 84, 143-147
55. Janse, C. J., Ramesar, J., and Waters, A. P. (2006) Nat. Protoc. 1, 346-356
56. DeLano, W. L. (2002) The PyMOL Molecular Graphics System, DeLano Scientific LLC, San Carlos, CA