Structure-based design of inhibitors specific for bacterial thymidylate synthase

Biochemistry

Volumn 38, Issue 5, 1999, Pages 1607-1617

  Stout, Thomas J ^a,d   Tondi, Donatella ^b,c   Rinaldi, Marcella ^c   Barlocco, Daniela ^c   Pecorari, P ^c   Santi, Daniel V ^a   Kuntz, Irwin D ^a   Stroud, Robert M ^a   Shoichet, Brian K ^b   Costi, M Paola ^c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

^c UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

^d MetaXen   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL ENZYME; ENZYME INHIBITOR; PHENOLPHTHALEIN; THYMIDYLATE SYNTHASE;

ARTICLE; CRYSTAL STRUCTURE; DRUG DESIGN; ENZYME INHIBITION; ENZYME SPECIFICITY; ENZYME STRUCTURE; LACTOBACILLUS CASEI; NONHUMAN; PRIORITY JOURNAL; SITE DIRECTED MUTAGENESIS;

AMINO ACID SUBSTITUTION; BACTERIAL PROTEINS; BINDING SITES; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; HUMANS; LACTOBACILLUS CASEI; MODELS, MOLECULAR; MUTAGENESIS, SITE-DIRECTED; PHENOLPHTHALEIN; SPECIES SPECIFICITY; SUBSTRATE SPECIFICITY; THYMIDYLATE SYNTHASE;

EID: 0033514283     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi9815896     Document Type: Article

References (42)

1. Hori, T., Ayusawa, D., Shimizu, K., Koyama, H., and Seno, T. (1984) Cancer Res. 44, 703-709.
2. Reyes, P., and Heidelberger, C. (1965) Mol. Pharmacol. I, 14-30.
3. Jones, T. R., Calvert, A. H., Jackman, A. L., Brown, S. J., Jones, J., and Harrap, K. R. (1981) Eur. J. Cancer 17, 11-19.
4. Santi, D. V., and Danenberg, P. V. (1984) in Folates and Pterins (Blakely, R. L., and Benkovic, S. J., Eds.) Vol. 1, pp 345-398, Wiley, New York.
5. Pinedo, H. M., and Peters, G. F. (1988) J. Clin. Oncol. 6, 1653-1664.
6. Appelt, K., Bacquet, R. J., Bartlett, C. A., Booth, C. L. J., Freer, S. T., Fuhry, M. A. M., Gehring, M. R., Herrmann, S. M., Howland, E. F., Janson, C. A., Jones, T. R., Kan, C. C., Kathardekar, V., Lewis, K. K., Marzoni, G. P., Matthews, D. A., Mohr, C., Moomaw, E. W., Morse, C. A., Oatley, S. J., Ogden, R. C., Reddy, M. R., Reich, S. H., Schoettlin, W. S., Smith, W. W., Varney, M. D., Villafranca, J. E., Ward, R. W., Webber, S., Webber, S. E., Welsh, K. M., and White, J. (1991) J. Med. Chem. 34, 1925-1934.
7. Jones, T. R., Varney, M. D., Webber, S. E., Lewis, K. K., Marzoni, G. P., Palmer, C. L., Kathardekar, V., Welsh, K. M., Webbe, S., Matthews, D. A., Appelt, K., Smith, W. W., Janson, C. A., Villafranca, J. E., Bacquet, R. J., Howland, E. F., Booth, C. L., Herrmann, S. M., Ward, R. W., White, J., Moomaw, E. W., Bartlett, C. A., and Morse, C. A. (1996) J. Med. Chem. 39, 904-917.
8. Klein, C., Chen, P., Arevalo, J. H., Stura, E. A., Marolewski, A., Warren, M. S., Benkovic, S. J., and Wilson, I. A. (1995) J. Mol. Biol. 249, 153-175.
9. Reich, S. H., Fuhry, M. A., Nguyen, D., Pino, M. J., Welsh, K. M., Webber, S., Janson, C. A., Jordan, S. R., Matthews, D. A., Smith, W. W., et al. (1992) J. Med. Chem. 35, 847-858.
10. Varney, M. D., Marzoni, G. P., Palmer, C. L., Deal, J. G., Webber, S., Welsh, K. M., Bacquet, R. J., Morse, C. A., Booth, C. L. J., Herrmann, S. M., Howland, E. F., Ward, R. W., and White, J. (1992) J. Med. Chem. 35, 663-676.
11. Webber, S. E., Bleckman, T. M., Attard, J., Deal, J. G., Kathardekar, V., Welsh, K. M., Webber, S., Janson, C. A., Matthews, D. A., and Smith, W. W. (1993) J. Med. Chem. 36, 733-746.
12. Carreras, C. W., and Santi, D. V. (1995) Annu. Rev. Biochem. 64, 721-762.
13. Gangjee, A., Mavandadi, F., Kisliuk, R. L., McGuire, J. J., and Queener, S. F. (1996) J. Med. Chem. 39, 4563-4568.
14. Shoichet, B. K., Perry, K. M., Santi, D. V., Stroud, R. M., and Kuntz, I. D. (1993) Science 259, 1445-1450.
15. Dale, G. E., Broger, C., Hartman, P. G., Langen, H., Page, M. G., Then, R. L., and Stuber, D. (1995) J. Bacteriol. 177, 2965-2970.
16. Costi, M. P., Barlocco, D., Rinaldi, M., Tondi, D., Pecorari, P., Ghelli, S., Stroud, R. M., Santi, D. V., Kuntz, I. D., Stout, T. J., Shoichet, B. K., Musiu, C., Marangiu, M. E., Pani, A., deMontis, A., Loi, A. G., and LaColla, P. (1998) J. Med. Chem. (submitted for publication).
17. Montfort, W. R., Perry, K. M., Fauman, E. B., Finer-Moore, J. S., Maley, G. F., Hardy, L., Maley, F., and Stroud, R. M. (1990) Biochemistry 29, 6964-6976.
18. Schiffer, C. A., Clifton, I. J., Davisson, V. J., Santi, D. V., and Stroud, R. M. (1995) Biochemistry 34, 16279-16287.
19. Climie, S., and Santi, D. V. (1990) Proc. Natl. Acad. Sci. U.S.A. 87, 633-637.
20. Davisson, V. J., Sirawaraporn, W., and Santi, D. V. (1989) J. Biol. Chem. 264, 9145-9148.
21. Davisson, V. J., Sirawarapom, W., and Santi, D. V. (1994) J. Biol. Chem. 269, 30740.
22. Pogolotti, A. L., Danenberg, P. V., and Santi, D. V. (1986) J. Med. Chem. 29, 478-482.
23. Huang, W., and Santi, D. V. (1994) J. Biol. Chem. 269, 31327-31329.
24. Climie, S. C., Carreras, C. W., and Santi, D. V. (1992) Biochemistry 31, 6032-6038.
25. Schellenberger, U., Francis, V. S. N. K., Balaram, P., Shoichet, B. K., and Santi, D. V. (1994) Biochemistry 33, 5623-5629.
26. Otwinowski, Z., and Minor, W. (1997) Methods Enzymol. 276, 307-326.
27. Laskowski, R. A., MacArthur, M. W., Moss, D. S., and Thornton, J. M. (1993) J. Appl. Crystallogr. 26, 283-291.
28. Brünger, A. T. (1992) X-PLOR Version 3.1. A System for X-ray Crystallography and NMR, Yale University Press, New Haven, CT.
29. Segel, I. H. (1975) Enzyme Kinetics, Wiley, New York.
30. Finer-Moore, J., Fauman, E. B., Foster, P. G., Perry, K. M., Santi, D. V., and Stroud, R. M. (1993) J. Mol. Biol. 232, 1101-1116.
31. Costi, M. P., unpublished results.
32. Bolin, J. T., Filman, D. J., Matthews, D. A., Hamlin, R. C., and Kraut, J. (1982) J. Biol. Chem. 257, 13650-13662.
33. Badger, J., Minor, I., Kremer, M. J., Oliveira, M. A., Smith, T. J., and Griffith, J. P. (1988) Proc. Natl. Acad. Sci. U.S.A. 85, 3304-3308.
34. Rutenber, E., Fauman, E. B., Keenan, R. J., Fong, S., Furth, P. S., Ortiz de Montellano, P. R., Meng, E., Kuntz, I. D., DeCamp, D. L., Salto, R., Rose, J. R., Craik, C. S., and Stroud, R. M. (1993) J. Biol. Chem. 268, 15343-15346.
35. Weber, P. C., Pantoliano, M. W., and Thompson, L. D. (1992) Biochemistry 31, 9350-9354.
36. Mattos, C., Rasmussen, B., Ding, X., Petsko, G. A., and Ringe, D. (1994) Nat. Struct. Biol. 1, 55-58.
37. Engh, R. A., Brandstetter, H., Sucher, G., Eichinger, A., Baumann, U., Bode, W., Huber, R., Poll, T., Rudolph, R., and Saal, W. v. d. (1996) Structure 4, 1353-1362.
38. Hoog, S. S., Zhao, B., Winborne, E., Fisher, S., Green, D. W., DesJarlais, R. L., Newlander, K. A., Callahan, J. F., Moor, M. L., and Huffman, W. F. (1995) J. Med. Chem. 38, 3246-3252.
39. Hill, T. L. (1989) Free energy transduction and biochemical cycle kinetics, Springer-Verlag, New York.
40. Hawkes, R., Grutter, M. G., and Schellman, J. (1984) J. Mol. Biol. 175, 195-212.
41. Jackman, A. L., Farrugia, D. C., Gibson, W., Kimbell, R., Harrap, K. R., Stephens, T. C., Azab, M., and Boyle, F. T. (1995) Eur. J. Cancer 31A (7-8), 1277-1282.
42. Cunningham, D., Zalcberg, J., Smith, I., Gore, M., Pazdur, R., Burris, H., Meropol, N. J., Kennealey, G., and Seymour, L. (1996) Ann. Oncol. 7 (2), 179-182.