(1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol as an inhibitor of ceramidase

Journal of Biological Chemistry

Volumn 271, Issue 21, 1996, Pages 12646-12654

  Bielawska, Alicja ^a   Greenberg, Mathew S ^a   Perry, David ^a   Jayadev, Supriya ^a   Shayman, James A ^b   McKay, Charles ^a   Hannun, Yusuf A ^a  

^a DUKE UNIVERSITY   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLSPHINGOSINE DEACYLASE; CERAMIDE DERIVATIVE; PHOSPHOPROTEIN PHOSPHATASE;

ARTICLE; CELL CYCLE G0 PHASE; CELL STRAIN HL 60; CONCENTRATION RESPONSE; DRUG EFFECT; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INHIBITION; GROWTH INHIBITION; GROWTH REGULATION; HUMAN; HUMAN CELL; PRIORITY JOURNAL; PROMYELOCYTIC LEUKEMIA;

AMIDOHYDROLASES; ENZYME ACTIVATION; ENZYME INHIBITORS; HUMANS; MYRISTATES; PHOSPHOPROTEIN PHOSPHATASE; PROPANOLAMINES; SUBSTRATE SPECIFICITY; TUMOR CELLS, CULTURED;

EID: 17544366509     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.271.21.12646     Document Type: Article

References (69)

1. Hannun, Y. A. (1994) J. Biol. Chem. 269, 3125-3128
2. Merrill, A. H., Jr. (1992) Nutr. Rev. 50, 78-80
3. Kolesnick, R., and Fuks, Z. (1995) J. Exp. Med. 181, 1949-1952
4. Chao, M. V. (1995) Mol. Cell. Neurosci. 6, 91-96
5. Liscovitch, M. (1992) Trends Biochem. Sci. 17, 393-399
6. Hannun, Y. A., and Obeid, L. M. (1995) Trends Biochem. Sci. 20, 73-77
7. Ballou, L. R., Chao, C. P., Holness, M. A., Barker, S. C., and Raghow, R. (1992) J. Biol. Chem. 267, 20044-20050
8. Quintans, J., Kilkus, J., McShan, C. L., Gottschalk, A. R., and Dawson, G. (1994) Biochem. Biophys. Res. Commun. 202, 710-714
9. Dobrowaky, R. T., Werner, M. H., Castellino, A. M., Chao, M. V., and Hannun, Y. A. (1994) Science 265, 1596-1599
10. Yanaga, F., and Watson, S. P. (1992) FEBS Lett. 314, 297-300
11. Dressler, K. A., Mathias, S., and Koleanick, R. N. (1992) Science 255, 1715-1718
12. Okazaki, T., Bielawska, A., Bell, R. M., and Hannun, Y. A. (1990) J. Biol. Chem. 268, 15823-15831
13. Bielawska, A., Linardic, C. M., and Hannun, Y. A. (1992) FEES Lett. 307, 211-214
14. Obeid, L. M., Linardic, C. M., Karolak, L. A., and Hannun, Y. A. (1993) Science 259, 1769-1771
15. Laulederkind, S. J. F., Bielawska, A., Raghow, R., Hannun, Y. A., and Ballou, L. R. (1995) J. Exp. Med. 182, 599-604
16. Goldkorn, T., Dressler, K. A., Muindi, J., Radin, N. S., Mendelsohn, J., Menaldino, D., Liotta, D., and Kolesnick, R. N. (1991) J. Biol. Chem. 266, 16092-16097
17. Bielawska, A., Crane, H. M., Liotta, D., Obeid, L. M., and Hannun, Y. A. (1993) J. Biol. Chem. 268, 26226-26232
18. Fishbein, J. D., Dobrowsky, R. T., Bielawska, A., Garrett, S., and Hannun, Y. A. (1993) J. Biol. Chem. 268, 9255-9261
19. Tepper, C. G., Jayadev, S., Liu, B., Bielawska, A., Wolff, R. A., Yonehara, S., Hannun, Y. A., and Seldin, M. F. (1995) Proc. Natl. Acad. Sci. U. S. A. 92, 8443-8447
20. Dobrowsky, R. T., Kamibayashi, C., Mumby, M. C., and Hannun, Y. A. (1993) J. Biol. Chem. 268, 15523-15530
21. Okazaki, T., Bell, R. M., and Hannun, Y. A. (1989) J. Biol. Chem. 264, 19076-19080
22. Mathias, S., Younes, A., Kan, C.-C., Orlow, I., Joseph, C., and Kolesnick, R. N. (1993) Science 259, 519-522
23. Abe, A., Inokuchi, J., Jimbo, M., Shimeno, H., Nagamatsu, A., Shayman, J. A., Shukla, G. S., and Radin, N. S. (1992) J. Biochem. (Tokyo) 111, 191-196
24. Wiegandt, H. (1985) in Glycolipids (Wiegandt, H., ed) pp. 199-259, Elsevier, New York
25. Merrill, A. H., Jr., and Jones, D. D. (1990) Biochim. Biophys. Acta 1044, 1-12
26. Van Echten, G and Sandhoff, K. (1993) J. Biol. Chem. 268, 5341-5344
27. Hakomori, S. (1981) Annu. Rev. Biochem. 50, 733-764
28. Spence, M. W., Beed, S., and Cook, H. W. (1986) Biochem. Cell Biol. 64, 400-404
29. Slife, C. W., Wang, E., Hunter, R., Wang, S., Burgess, C., Liotta, D. C., and Merrill, A. H., Jr. (1989) J. Biol. Chem. 264, 10371-10377
30. Bielawska, A., Linardic, C. M., and Hannun, Y. A. (1992) J. Biol. Chem. 267, 18493-18497
31. Carter, E., and Fujino, Y. (1956) J. Biol. Chem. 221, 879-884
32. Stoffel, W. (1973) Chem. Phys. Lipids 11, 318-334
33. Nimkar, S., Menaldino, D., Merrill, A. H., Jr., and Liotta, D. C. (1988) Tetrahedron Lett. 29, 3037-3040
34. Garner, P., Park, J. M., and Malecki, E. (1988) J. Org. Chem. 53, 4395-4398
35. Herold, P. (1988) Helv. Chim. Acta 71, 354-362
36. Merrill, A. H., Jr., Nimkar, S., Menaldino, D., Hannun, Y. A., Loomis, C., Bell, R. M., Tyagi, S. R., Lambeth, J. D., Stevens, V. L., Hunter, R., and Liotta, D. C. (1989) Biochemistry 28, 3138-3145
37. Chao, R., Khan, W., and Hannun, Y. A. (1992) J. Biol. Chem. 267, 23459-23462
38. Jayadev, S., Liu, B., Bielawska, A. E., Lee, J. Y., Nazaire, F., Pushkareva, M. Y., Obeid, L. M., and Hannun, Y. A. (1995) J. Biol. Chem. 270, 2047-2052
39. Gatt, S., and Yavin, E. (1969) Methods Enzymol. 14, 139-144
40. Dobrowsky, R. T., and Hannun, Y. A. (1992) J. Biol. Chem. 267, 5048-5051
41. Wolff, R. A., Dobrowsky, R. T., Bielawska, A., Obeid, L. M., and Hannun, Y. A. (1994) J. Biol. Chem. 269, 19605-19609
42. Sugita, M., Williams, M., Dulaney, J. T., and Moser, H. W. (1975) Biochim. Biophys. Acta 398, 125-131
43. Wertz, P. W., and Downing, D. T. (1990) FEBS Lett. 268, 110-112
44. Coroneos, E., Martinez, M., McKenna, S., and Kester, M. (1995) J. Biol. Chem. 270, 23305-23309
45. Wang, E., Norred, W. P., Bacon, C. W., Riley, R. T., and Merrill, A. H., Jr. (1991) J. Biol. Chem. 266, 14486-14490
46. Bernardo, K., Hurwitz, R., Zenk, T., Desnick, R. J., Ferlinz, K., Schuchman, E. H., and Sandhoff, K. (1995) J. Biol. Chem. 270, 11098-11102
47. Chen, W. W., Moser, A. B., and Moser, H. W. (1981) Arch. Biochem. Biophys. 208, 444-455
48. Linardic, C. M., and Hannun, Y. A. (1994) J. Biol. Chem. 269, 23530-23537
49. Merrill, A. H., Jr., and Wang, E. (1992) Methods Enzymol. 209, 427-437
50. Merrill, A. H., Jr., Sereni, A., Stevens, V. L., Hannun, Y. A., Bell, R. M., and Kinkade, J. M., Jr. (1986) J. Biol. Chem. 261, 12610-12615
51. Spiegel, S., Olivera, A., Zhang, H., Thompson, E. W., Su, Y., and Berger, A. (1994) Breast Cancer Res. Treat. 31, 337-348
52. Buehrer, B. M., and Bell, R. M. (1993) Adv. Lipid Res. 26, 59-67
53. Pushkareva, M., Chao, R., Bielawska, A., Merrill, A. H., Jr., Crane, H. M., Lagu, B., Liotta, D., and Hannun, Y. A. (1995) Biochemistry 34, 1885-1892
54. Yatomi, Y., Ruan, F., Hakomori, S., and Igarashi, Y. (1995) Blood 86, 193-202
55. Hannun, Y. A., Loomis, C. R., Merrill, A. H., Jr., and Bell, R. M. (1986) J. Biol. Chem. 261, 12604-12609
56. Hannun, Y. A., Merrill, A. H., Jr., and Bell, R. M. (1991) Methods Enzymol. 201, 316-328
57. Barbour, S., Edidin, M., Felding-Habermann, B., Taylor-Norton, J., Radin, N. S., and Fenderson, B. A. (1992) J. Cell. Physiol. 150, 610-619
58. Rani, C. S. S., Abe, A., Chang, Y., Rosenzweig, N., Saltiel, A. R., Radin, N. S., and Shayman, J. A. (1995) J. Biol. Chem. 270, 2859-2867
59. Inokuchi, J., Jimbo, M., Momosaki, K., Shimeno, H., Nagamatsu, A., and Radin, N. S. (1990) Cancer Res. 50, 6731-6737
60. Inokuchi, J., Momosaki, K., Shimeno, H., Nagamatsu, A., and Radin, N. S. (1989) J. Cell. Physiol. 141, 573-583
61. Uemura, K., Sugiyama, E., and Taketomi, T. (1991) J. Biochem. (Tokyo) 110, 96-102
62. Dbaibo, G., Pushkareva, M. Y., Jayadev, S., Schwartz, J. K., Horowitz, J. M., Obeid, L. M., and Hannun, Y. A. (1995) Proc. Natl. Acad. Sci. U. S. A. 92, 1347-1351
63. Lavie, Y., and Liscovitch, M. (1990) J. Biol. Chem. 265, 3868-3872
64. Kiss, Z., Crilly, K. S., Rossi, M. A., and Anderson, W. B. (1992) Biochim. Biophys. Acta 1124, 300-302
65. Gomez-Muñoz, A., Martin, A., O'Brien, L., and Brindley, D. N. (1994) J. Biol. Chem. 269, 937-8943
66. Nakamura, T., Abe, A., Balazovich, K. J., Wu, D., Suchard, S. J., Boxer, L. A., and Shayman, J. A. (1994) J. Biol. Chem. 269, 18384-18389
67. Venable, M. E., Blobe, G. C., and Obeid, L. M. (1994) J. Biol. Chem. 269, 26040-26044
68. Kiss, Z., and Deli, E. (1995) FEES Lett. 365, 146-148
69. Jones, M. J., and Murray, A. W. (1995) J. Biol. Chem. 270, 5007-5013