2-Cyano-3,12-dioxooleana-1,9-dien-28-imidazolide (CDDO-Im) directly targets mitochondrial glutathione to induce apoptosis in pancreatic cancer

Journal of Biological Chemistry

Volumn 280, Issue 43, 2005, Pages 36273-36282

  Samudio, Ismael ^a   Konopleva, Marina ^a   Hail Jr , Numsen ^a   Shi, Yue Xi ^a   McQueen, Teresa ^a   Hsu, Timothy ^a   Evans, Randall ^a   Honda, Tadashi ^b   Gribble, Gordon W ^b   Sporn, Michael ^b   Gilbert, Hiram F ^c   Safe, Stephen ^d   Andreeff, Michael ^a  

^a UNIVERSITY OF TEXAS MD ANDERSON CANCER CENTER   (United States)

^b DARTMOUTH MEDICAL SCHOOL   (United States)

^c BAYLOR COLLEGE OF MEDICINE   (United States)

^d TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; CYTOLOGY; DISEASES; KETONES; METABOLISM; ONCOLOGY; PATIENT TREATMENT; TRANSPLANTATION (SURGICAL); TUMORS;

CHEMORESISTANT TUMORS; MITOCHONDRIAL GLUTATHIONE; PANCREATIC CANCER; SURGICAL RESECTION;

NITROGEN COMPOUNDS;

2 CYANO 3,12 DIOXOOLEANA 1,9 28 IMIDAZOLIDE; ANTIOXIDANT; DITHIOTHREITOL; GLUTATHIONE; GLUTATHIONE PEROXIDASE; IMIDAZOLIDINE DERIVATIVE; PHOSPHATIDYLSERINE; REACTIVE OXYGEN METABOLITE; THIOL DERIVATIVE; TRITERPENOID; UNCLASSIFIED DRUG;

ADVANCED CANCER; ALKYLATION; ANIMAL CELL; APOPTOSIS; ARTICLE; BIOTINYLATION; CELL DEATH; CELL VIABILITY; MEMBRANE POTENTIAL; MITOCHONDRIAL MEMBRANE; NONHUMAN; OXIDATION REDUCTION REACTION; PANCREAS CANCER; PRIORITY JOURNAL; RISK BENEFIT ANALYSIS; TARGET CELL; TUMOR GROWTH;

ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; APOPTOSIS; BINDING SITES; BIOTINYLATION; CASPASES; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; CYTOPLASM; DNA FRAGMENTATION; ENZYME ACTIVATION; FLOW CYTOMETRY; GLUTATHIONE; HUMANS; IMIDAZOLES; MEMBRANE POTENTIALS; MITOCHONDRIA; MODELS, CHEMICAL; OLEANOLIC ACID; PANCREATIC NEOPLASMS; REACTIVE OXYGEN SPECIES; SULFHYDRYL COMPOUNDS; TIME FACTORS;

ANIMALIA;

EID: 27744464884     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.M507518200     Document Type: Article

References (52)

1. Abbruzzese, J. L. (2003) Int. J. Gastrointest. Cancer 33, 1-2
2. National Cancer Institute (2002) Surveillance, Epidemiology, and End Results Fast Stats: Pancreatic Cancer http://seer.cancer.gov
3. Li, D., Xie, K., Wolff, R., and Abbruzzese, J. L. (2004) Lancet 363, 1049-1057
4. Abbruzzese, J. L. (2002) Semin. Oncol. 29, 2-8
5. Wu, G., Fang, Y. Z., Yang, S., Lupton, J. R., and Turner, N. D. (2004) J. Nutr. 134, 489-492
6. Imai, H., and Nakagawa, Y. (2003) Free Radic. Biol. Med. 34, 145-169
7. Filomeni, G., Rotilio, G., and Ciriolo, M. R. (2003) FASEB J. 17, 64-66
8. Hancock, J.T., Desikan, R., and Neill, S. J. (2003) Ann. N. Y. Acad Sci. 1010, 446-448
9. Schafer, F. Q., and Buettner, G. R. (2001) Free Radic. Biol. Med. 30, 1191-1212
10. Coffey, R. N., Watson, R. W., Hegarty, N. J., O'Neill, A., Gibbons, N., Brady, H. R., and Fitzpatrick, J. M. (2000) Cancer 88, 2092-2104
11. Rizzardini, M., Lupi, M., Bernasconi, S., Mangolini, A., and Cantoni, L. (2003) J. Neurol. Sci. 207, 51-58
12. Dhanbhoora, C. M., and Babson, J. R. (1992) Arch. Biochem. Biophys. 293, 130-139
13. Fernandez-Checa, J. C., Kaplowitz, N., Garcia-Ruiz, C, and Colell, A. (1998) Semin. Liver Dis. 18, 389-401
14. Fernandez-Checa, J. C. (2003) Biochem. Biophys. Res. Commun. 304, 471-479
15. Colell, A., Garcia-Ruiz, C., Miranda, M., Ardite, E., Mari, M., Morales, A., Corrales, F., Kaplowitz, N., and Fernandez-Checa, J. C. (1998) Gastroenterology 115, 1541-1551
16. Colell, A., Coll, O., Garcia-Ruiz, C., Paris, R., Tiribelli, C., Kaplowitz, N., and Fernandez-Checa, J. C. (2001) Hepatology 34, 964-971
17. Chernyak, B. V. (1997) Biosci. Rep. 17, 293-302
18. Costantini, P., Chernyak, B. V., Petronilli, V., and Bernardi, P. (1996) J. Biol. Chem. 271, 6746-6751
19. Inoue, S., Snowden, R. T., Dyer, M. J., and Cohen, G. M. (2004) Leukemia 18, 948-952
20. Ito, Y., Pandey, P., Place, A., Sporn, M. B., Gribble, G. W., Honda, T., Kharbanda, S., and Kufe, D. (2000) Cell Growth & Differ. 11, 261-267
21. Konopleva, M., Tsao, T., Estrov, Z., Lee, R. M., Wang, R. Y., Jackson, C. E., McQueen, T., Monaco, G., Munsell, M., Belmont, J., Kantarjian, H., Sporn, M. B., and Andreeff, M. (2004) Cancer Res. 64, 7927-7935
22. Suh, W. S., Kim, Y. S., Schimmer, A. D., Kitada, S., Minden, M., Andreeff, M., Suh, N., Sporn, M., and Reed, J. C. (2003) Leukemia 17, 2122-2129
23. Chauhan, D., Li, G., Podar, K., Hideshima, T., Shringarpure, R., Catley, L., Mitsiades, C., Munshi, N., Tai, Y. T., Suh, N., Gribble, G. W., Honda, T., Schlossman, R., Richardson, P., Sporn, M. B., and Anderson, K. C. (2004) Blood 103, 3158-3166
24. Ikeda, T., Nakata, Y., Kimura, F., Sato, K., Anderson, K., Motoyoshi, K., Sporn, M., and Kufe, D. (2004) Mol. Cancer Ther. 3, 39-45
25. Lapillonne, H., Konopleva, M., Tsao, T., Gold, D., McQueen, T., Sutherland, R. L., Madden, T., and Andreeff, M. (2003) Cancer Res. 63, 5926-5939
26. Kim, K. B., Lotan, R., Yue, P., Sporn, M. B., Suh, N., Gribble, G. W., Honda, T., Wu, G. S., Hong, W. K., and Sun, S. Y. (2002) Mol. Cancer Ther. 1, 177-184
27. Ito, Y., Pandey, P., Sporn, M. B., Datta, R., Kharbanda, S., and Kufe, D. (2001) Mol. Pharmacol. 59, 1094-1099
28. Hail, N., Jr., Konopleva, M., Sporn, M., Lotan, R., and Andreeff, M. (2004) J. Biol. Chem. 279, 11179-11187
29. Place, A. E., Suh, N., Williams, C. R., Risingsong, R., Honda, T., Honda, Y., Gribble, G. W., Leesnitzer, L. M., Stimmel, J. B., Willson, T. M., Rosen, E., and Sporn, M. B. (2003) Clin. Cancer Res. 9, 2798-2806
30. Ikeda, T., Sporn, M., Honda, T., Gribble, G. W., and Kufe, D. (2003) Cancer Res. 63, 5551-5558
31. Honda, T., Janosik, T., Honda, Y., Han, J., Liby, K. T., Williams, C. R., Couch, R. D., Anderson, A. C, Sporn, M. B., and Gribble, G. W. (2004) J. Med. Chem. 47, 4923-4932
32. Honda, T., Honda, Y., Favaloro, F. G., Jr., Gribble, G. W., Suh, N., Place, A. E., Rendi, M. H., and Sporn, M. B. (2002) Bioorg. Med. Chem. Lett. 12, 1027-1030
33. Suh, N., Wang, Y., Honda, T., Gribble, G. W., Dmitrovsky, E., Hickey, W. F., Maue, R. A., Place, A. E., Porter, D. M., Spinella, M. J., Williams, C. R., Wu, G., Dannenberg, A. J., Flanders, K. C., Letterio, J. J., Mangelsdorf, D. J., Nathan, C. F., Nguyen, L., Porter, W. W., Ren, R. F., Roberts, A. B., Roche, N. S., Subbaramaiah, K., and Sporn, M. B. (1999) Cancer Res. 59, 336-341
34. Fernandez-Checa, J. C., Garcia-Ruiz, C., Colell, A., Morales, A., Mari, M., Miranda, M., and Ardite, E. (1998) Biofactors 8, 7-11
35. Ravagnan, L., Roumier, T., and Kroemer, G. (2002) J. Cell Physlol. 192, 131-137
36. Minns, L. A., Buzoni-Gatel, D., Ely, K. H, Rachinel, N., Luangsay, S., and Kasper, L. H. (2004) Gastroenterologe 127, 119-126
37. Konopleva, M., Tsao, T., Ruvolo, P., Stiouf, I., Estrov, Z., Leysath, C. E., Zhao, S., Harris, D., Chang, S., Jackson, C. E., Munsell, M., Suh, N., Gribble, G., Honda, T., May, W. S., Sporn, M. B., and Andreeff, M. (2002) Blood 99, 326-335
38. Yao, P. M., and Tabas, I. (2001) J. Biol. Chem. 276, 42468-42476
39. Zou, W., Liu, X., Yue, P., Zhou, Z., Sporn, M. B., Lotan, R., Khuri, F. R., and Sun, S. Y. (2004) Cancer Res. 64, 7570-7578
40. Wang, Y., Porter, W. W., Suh, N., Honda, T., Gribble, G. W., Leesnitzer, L. M., Plunket, K. D., Mangelsdorf, D. J., Blanchard, S. G., Willson, T. M., and Sporn, M. B. (2000) Mol. Endocrinol. 14, 1550-1556
41. Melichar, B., Konopleva, M., Hu, W., Melicharova, K., Andreeff, M., and Freedman, R. S. (2004) Gynecol. Oncol. 93, 149-154
42. Duxbury, M.S., Ito, H., Benoit, E., Zinner, M. J., Ashley, S.W., and Whang, E. E. (2004) Surgery 136, 261-269
43. Duxbury, M. S., Ito, H., Zinner, M. J., Ashley, S. W., and Whang, E. E. (2004) Clin. Cancer Res. 10, 2307-2318
44. Anderson, K. M., Seed, T., Meng, J., Ou, D., Alrefai, W. A., and Harris, J. E. (1998) Anticancer Res. 18, 791-800
45. Latham, P., Lund, E. K., Brown, J. C., and Johnson, I. T. (2001) Gut 49, 97-105
46. Saeki, K., Kobayashi, N., Inazawa, Y., Zhang, H., Nishitoh, H., Ichijo, H., Saeki, K., Isemura, M., and Yuo, A. (2002) Biochem. J. 368, 705-720
47. Dragovich, P. S., Webber, S. E., Babine, R. E., Fuhrman, S. A., Patick, A. K., Matthews, D. A., Lee, C. A., Reich, S. H., Prins, T. J., Marakovits, J. T., Littlefield, E. S., Zhou, R., Tikhe, J., Ford, C. E., Wallace, M. B., Meador, J. W., III, Ferre, R. A., Brown, E. L., Binford, S. L., Harr, J. E., DeLisle, D. M., and Worland, S. T. (1998) J. Med. Chem. 41, 2806-2818
48. Myers, A. G., and Herzon, S. B. (2003) J. Am. Chem. Soc. 125, 12080-12081
49. Woynarowska, B. A., and Woynarowski, J. M. (2002) Biochim. Biophys. Acta 1587, 309-317
50. Herzig, M. C., Liang, H., Johnson, A. E., Woynarowska, B., and Woynarowski, J. M. (2002) Breast Cancer Res. Treat. 71, 133-143
51. Dinkova-Kostova, A. T., Liby, K. T., Stephenson, K. K., Holtzclaw, W. D., Gao, X., Suh, N., Williams, C., Risingsong, R., Honda, T., Gribble, G. W., Sporn, M. B., and Talalay, P. (2005) Proc. Natl. Acad. Sci. U. S. A. 102, 4584-4589
52. Coll, O., Colell, A., Garcia-Ruiz, C., Kaplowitz, N., and Fernandez-Checa, J. C. (2003) Hepatology 38, 692-702