Selective peptidic and peptidomimetic inhibitors of Candida albicans MyristoylCoA : Protein N-myristoyltransferase: A new approach to antifungal therapy

Biopolymers

Volumn 43, Issue 1, 1997, Pages 43-71

  Sikorski, James A ^a   Devadas, Balekudru ^a   Zupec, Mark E ^a   Freeman, Sandra K ^a   Brown, David L ^a   Lu, Hwang Fun ^a   Nagarajan, Srinivasan ^a   Mehta, Pramod P ^a   Wade, Arlene C ^a   Kishore, Nandini S ^a   Bryant, Martin L ^a   Getman, Daniel P ^a,b   McWherter, Charles A ^a,b   Gordon, Jeffrey I ^b  

^a MONSANTO COMPANY   (United States)

^b WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Antifungal therapy: Candida albicans; Myristoyl CoA:protein N myristoyltransferase; Peptidamimetic inhibitors; Peptidic inhibitors

Indexed keywords

CHEMICAL BONDS; ENZYME KINETICS; FUNGUS RESISTANCE; GROWTH KINETICS;

ANTIFUNGAL THERAPY; CANDIDA ALBICANS; PEPTIDOMIMETIC INHIBITORS;

ENZYME INHIBITION;

ACYLTRANSFERASE; ANTIFUNGAL AGENT; ENZYME INHIBITOR; GLYCYLPEPTIDE N-TETRADECANOYLTRANSFERASE; PEPTIDE; PROTEIN N MYRISTOYLTRANSFERASE;

CANDIDA ALBICANS; CHEMISTRY; COMPARATIVE STUDY; DRUG ANTAGONISM; DRUG EFFECT; ENZYMOLOGY; HUMAN; REVIEW; STRUCTURE ACTIVITY RELATION;

ACYLTRANSFERASES; ANTIFUNGAL AGENTS; CANDIDA ALBICANS; ENZYME INHIBITORS; HUMANS; PEPTIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030612443     PISSN: 00063525     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0282(1997)43:1<43::AID-BIP5>3.0.CO;2-0     Document Type: Article

References (58)

1. Zhang, F. L. & Casey, P. J. (1996) Ann. Rev. Biochem. 65, 241-269.
2. Johnson, D. R., Bhatnagar, R. S., Knoll, L. J. & Gordon, J. I. (1994) Ann. Rev. Biochem. 63, 869-914.
3. Chow, M. & Moscufo, N. (1995) Methods Enzymol. 250, 495-509.
4. Peitzsch, R. M. & McLaughlin, S. (1993) Biochemistry 32, 10436-10443.
5. Mosior, M. & McLaughlin, S. (1992) Biochemistry 31, 1767-1773.
6. McLaughlin, S. & Aderem, A. (1995) Trends Biochem. Sci. 20, 272-276.
7. Seykora, J. T., Myat, M. M., Allen, L.-A. H., Ravetch, J. V. & Aderem, A. (1996) J. Biol. Chem. 271, 18797-18802.
8. Swierczynski, S. L. & Blackshear, P. J. (1996) J. Biol. Chem. 271, 23424-23430.
9. Zozulya, S. & Stryer, L. (1992) Proc. Natl. Acad. Sci. USA 89, 11569-11573.
10. Cheng, C.-K., Inglese, J., Lefkowitz, R. J. & Hurley, J. B. (1995) J. Biol. Chem. 270, 18060-18066.
11. Klenchin, V. A., Calvert, P. D. & Bownds, M. D. (1995) J. Biol. Chem. 270, 16147-16152.
12. Ames, J. B., Tanaka, T., Ikura, M. & Stryer, L. (1995) J. Biol. Chem. 270, 30909-30913.
13. Kokame, K., Fukada, Y., Yoshizawa, T., Takoa, T. & Shimonishi, Y. (1992) Nature 359, 749-752.
14. Neubert, T. A., Johnson, R. S., Hurley, J. B. & Walsh, K. A. (1992) J. Biol. Chem. 267, 18274-18277.
15. Palczewski, K., Subbaraya, I., Gorczyca, W. A., Helekar, B. S., Ruiz, C. C., Ohguro, H., Huang, J., Zhao, X., Crabb, J. W. & Johnson, R. S. (1994) Neuron 13, 395-404.
16. Dizhoor, A. M., Ericcson, L. H., Johnson, R. S., Kumar, S., Olshevskya, E., Zozulya, S., Neubert, T. A., Stryer, L., Hurley, J. B. & Walsh, K. A. (1992) J. Biol. Chem. 267, 16033-16036.
17. Johnson, R. S., Oghuro, H., Palczewski, K., Hurley, J. B., Walsh, K. A. & Neubert, T. A. (1994) J. Biol. Chem. 269, 21067-21071.
18. Dupont, B., Graybill, J. R., Armstrong, D., Laroche, R., Touze, J. E. & Wheat, L. J. (1992) J. Med. Vet. Mycol. 30, 19-28.
19. Georgopapadakou, N. H. & Walsh, T. J. (1994) Science 264, 371-373.
20. Powderly, W. G., Finkelstein, D. M., Feinberg, J., Frame, P., He, W., van der Horst, C., Koletar, S. L., Eyster, M. E., Carey, J., Waskin, H., et al. (1995) New Engl. J. Med. 332, 739-740.
21. Wiegand, R. C., Carr, C., Minnerly, J. C., Pauley, A. M., Carron, C. P., Carr, C. Z., Langner, C., Duronio, R. J. & Gordon, J. I. (1992) J. Biol. Chem. 267, 8591-8598.
22. Duronio, R. J., Reed, S. I. & Gordon, J. I. (1992) Proc. Natl. Acad. Sci. USA 89, 4129-4133.
23. Langner, C. A., Lodge, J. K., Travis, S. J., Caldwell, J. E., Lu, T., Li, Q., Bryant, M. L., Devadas, B., Gokel, G. W., Kobayashi, G. S. & Gordon, J. I. (1992) J. Biol. Chem. 267, 17159-17169.
24. Denich, K. T., Malloy, P. J. & Feldman, D. (1992) Gene 110, 123-128.
25. Lodge, J. K., Johnson, R. L., Weinberg, R. A. & Gordon, J. I. (1994) J. Biol. Chem. 269, 2996-30094.
26. Weinberg, R. A., McWherter, C. A., Freeman, S. K., Wood, D. C., Gordon, J. I. & Lee, S. C. (1995) Mol. Microbiol. 16, 241-250.
27. Lodge, J. K., Jackson-Machelski, E., Devadas, B., Zupec, M. E., Getman, D. P., Kishore, N., Freeman, S. K., McWherter, C. A., Sikorski, J. A. & Gordon, J. I. (1997) Microbiology 143, 357-366.
28. Boman, A. L. & Kahn, R. A. (1995) Trends Biochem. Sci. 20, 147-150.
29. Randazzo, P. A. & Kahn, R. A. (1995) Methods Enzymol. 250, 394-405.
30. Kahn, R. A., Clark, J., Rulka, C., Stearns, T., Zhang, C., Randazzo, P. A., Terui, T. & Cavenagh, M. (1995) J. Biol. Chem. 270, 143-150.
31. Rudnick, D. A., McWherter, C. A., Rocque, W. J., Lennon, P. J., Getman, D. P. & Gordon, J. I. (1991) J. Biol. Chem, 266, 9732-9739.
32. Bhatnagar, R. S., Jackson-Machelski, E., McWherter, C. A. & Gordon, J. I. (1994) J. Biol. Chem. 269, 11045-11053.
33. Rocque, W. J., McWherter, C. A., Wood, D. C. & Gordon, J. I. (1993) J. Biol. Chem. 268, 9964-9971.
34. Kishore, N. S., Lu, T., Knoll, L. J., Katoh, A., Rudnick, D. A., Mehta, P. P., Devadas, B., Huhn, M., Atwood, J. L., Adams, S. P., Gokel, G. W. & Gordon, J. I. (1991) J. Biol. Chem. 266, 8835-8855.
35. Kishore, N. S., Wood, D. C., Mehta, P. P., Wade, A. C., Lu, T., Gokel, G. W. & Gordon, J. I. (1993) J. Biol. Chem. 268, 4889-4902.
36. Paige, L. A., Zheng, G., DeFrees, S. A., Cassady, J. M. & Geahlen, R. L. (1989) J. Med. Chem. 32, 1667-1673.
37. Rudnick, D. A., Johnson, R. L. & Gordon, J. I. (1992) J. Biol. Chem. 267, 23852-23861.
38. Devadas, B., Zupec, M. E., Freeman, S. K., Brown, D. L., Nagarajan, S., Sikorski, J. A., McWherter, C. A., Getman, D. P. & Gordon, J. I. (1995) J. Med. Chem. 38, 1837-1840.
39. Devadas, B., Freeman, S. K., McWherter, C. A., Kuneman, D. W., Vinjamoori, D. V. & Sikorski, J. A. (1996) Bioorg. Med. Chem. Lett. 6, 1977-1982.
40. Brown, D. L., Devadas, B., Lu, H.-F., Nagarajan, S., Zupec, M. E., Freeman, S. K., McWherter, C. A., German, D. P. & Sikorski, J. A. (1997) Bioorg. Med. Chem. Lett. 7, 379-382.
41. Devadas, B., Freeman, S. K., Lu, H.-F., Zupec, M. E., McWherter, C. A., Kuneman, D. W., Vinjamoori, D. V., Getman, D. P., Gordon, J. I. & Sikorski, J. A. (1997) J. Med. Chem., submitted.
42. Nagarajan, S., Devadas, B., Zupec, M. E., Freeman, S. K., Brown, D. L., Lu, H.-F., Mehta, P. P., Kishore, N, S., McWherter, C. A., Getman, D. P., Gordon, J. I. & Sikorski, J. A. (1997) J. Med. Chem. 40, in press.
43. McWherter, C. A., Rocque, W, J., Zupec, M. E., Freeman, S. K., Brown, D. L., Devadas, B., Getman, D. P., Sikorski, J. A. & Gordon, J. I. (1997) J. Biol. Chem., 272, in press.
44. Rudnick, D. A., Rocque, W. J., McWherter, C. A., Toth, M. V., Jackson-Machelski, E. & Gordon, J. I. (1993) Proc. Natl. Acad. Sci. USA 90, 1087-1091.
45. Stearns, T., Kahn, R. A., Botstein, D. & Hoyt, M. A. (1990) Mol. Cell. Biol. 10, 6690-6699.
46. Lee, F. S., Stevens, L. A., Kao, Y. L., Moss, J. & Vaughan, M. (1994) J. Biol. Chem. 269, 20931-20937.
47. Kahn, R. A., Clark, J., Rulka, C., Stearns, T., Zhang, C., Randazzo, P. A., Terui, T. & Cavenagh, M. (1995) J. Biol. Chem. 270, 143-150.
48. Randazzo, A. R. & Kahn, R. A. (1995) Methods Enzymol. 250, 394-405.
49. Boman, A. L. & Kahn, R. A. (1995) Trends Biochem. Sci. 20, 147-150.
50. Duronio, R. J., Rudnick, D. A., Johnson, R. L., Linder, M. E. & Gordon, J. I. (1990) Proc. Natl. Acad. Sci, USA 87, 1506-1510.
51. Duronio, R. J., Rudnick, D. A., Johnson, R. L., Linder, M. E. & Gordon, J. I. (1990) Methods Enzymol 1, 253-263.
52. Cunningham, B. C. & Wells, J. A. (1989) Science 244, 1081-1085.
53. Rudnick, D. A., McWherter, C. A., Gokel, G. W. & Gordon, J. I. (1993) Adv. Enzymol. 67, 375-430.
54. Stryer, L. (1988) in Biochemistry, W. H. Freeman, New York, pp. 20-21.
55. Catalan, J., Abboud, J. L. & Elguero, J. (1987) Adv. Heterocycl. Chem. 41, 187-274.
56. Ganellin, C. R. (1975) in Molecular and Quantum Pharmacology, Bergmann, E. D. & Pullman, B., Eds., D. Reidel, Boston, MA, p. 43.
57. Zhang, L., Jackson-Machelski, E. & Gordon, J. I. (1996) J. Biol. Chem. 271, 33131-33140.
58. Peseckis, S. M. & Resh, M. D. (1994) J. Biol. Chem. 269, 30888-30892.