Inhibition of hypoxia-inducible transcription factor complex with designed epipolythiodiketopiperazine

Biopolymers

Volumn 95, Issue 1, 2011, Pages 8-16

  Kushal, Swati ^a,b   Wang, Hui ^b   LáSzló, Csaba F ^b,c   SzáBo, Lajos Z ^b   Olenyuk, Bogdan Z ^a,b,c  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b University of Arizona   (United States)

^c UNIVERSITY OF ARIZONA   (United States)

Author keywords

Angiogenesis; Epipolythiodiketopiperazine; Hypoxia inducible factor; Transcription

Indexed keywords

ANGIOGENESIS; BIOLOGICAL ACTIVITIES; CULTURED CELL; DOSE-DEPENDENT MANNER; DOWN-REGULATION; EPIPOLYTHIODIKETOPIPERAZINE; HYPOXIA-INDUCIBLE FACTOR 1; HYPOXIA-INDUCIBLE FACTORS; HYPOXIA-INDUCIBLE TRANSCRIPTION FACTORS; INDUCIBLE GENE EXPRESSION; MECHANISTIC STUDIES; RESEARCH TOOLS; SMALL MOLECULE INHIBITOR; SYNTHESIS EVALUATION; TRANSACTIVATION DOMAIN; TRANSCRIPTIONAL CO-ACTIVATORS;

AMINO ACIDS; GENES; MOLECULAR BIOLOGY; TRANSCRIPTION FACTORS;

TRANSCRIPTION;

1 [(1H INDOL 3 YL)METHYL) 6 (HYDROXYMETHYL) 7,9 DIMETHYL 2,3,4,5 TETRATHIA 7,9 DIAZABICYCLO[4.2.2]DECANE 8,10 DIONE; ANTINEOPLASTIC AGENT; GLIOTOXIN; HYALODENDRIN; HYPOXIA INDUCIBLE FACTOR 1ALPHA; PROTEIN P300; TERT BUTYL 3 [5 [(BENZYLOXY)METHYL] 3 (4 METHOXYPHENYL) 6,8 DIMETHYL 7,9 DIOXO 2,4 DITHIA 6,8-DIAZABICYCLO[3.2.2]NONAN 1 YL] 1H INDOLE 1 CARBOXYLATE; UNCLASSIFIED DRUG; VASCULOTROPIN;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CARBOXY TERMINAL SEQUENCE; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DOWN REGULATION; DRUG DESIGN; DRUG SYNTHESIS; GENE EXPRESSION; HUMAN; HUMAN CELL; IN VITRO STUDY;

AMINO ACID SEQUENCE; CELL LINE, TUMOR; CELL SURVIVAL; GENE EXPRESSION REGULATION; HUMANS; HYPOXIA-INDUCIBLE FACTOR 1; MOLECULAR SEQUENCE DATA; PIPERAZINES;

EID: 78049434478     PISSN: 00063525     EISSN: 10970282     Source Type: Journal    
DOI: 10.1002/bip.21550     Document Type: Article

References (49)

1. Brown, J. M.;Wilson, W. R. Nat Rev Cancer 2004, 4, 437-447.
2. Vaupel, P.;Mayer, A. Cancer Metastasis Rev 2007, 26, 225-239.
3. Carmeliet, P. Nature 2005, 438, 932-936.
4. Carmeliet, P.;Jain, R. K. Nature 2000, 407, 249-257.
5. Dames, S. A.;Martinez-Yamout, M.;De Guzman, R. N.;Dyson, H. J.;Wright, P. E. Proc Natl Acad Sci USA 2002, 99, 5271-5276.
6. Dewhirst, M. W.;Cao, Y.;Moeller, B. Nat Rev Cancer 2008, 8, 425-437.
7. Roskoski, R. Crit Rev Oncol/Hematol 2007, 62, 179-213.
8. Ristow, M. Curr Opin Clin Nutr Metab Care 2006, 9, 339-345.
9. Pugh, C. W.;Ratcliffe, P. J. Nat Med 2003, 9, 677-684.
10. Semenza, G. L. Intern Med 2002, 41, 79-83.
11. Quintero, M.;Mackenzie, N.;Brennan, P. A. Eur J Surg Oncol 30: 465-468, 2004.
12. Kaelin, W. G. Biochem Biophys Res Commun 2005, 338, 627-638.
13. Kaelin, W. G. Annu Rev Biochem 2005, 74, 115-128.
14. O'Rourke, J. F.;Dachs, G. U.;Gleadle, J. M.;Maxwell, P. H.;Pugh, C. W.;Stratford, I. J.;Wood, S. M.;Ratcliffe, P. J. Oncol Res 1997, 9, 327-332.
15. Vo, N.;Goodman, R. H. J Biol Chem 2001, 276, 13505-13508.
16. Kung, A. L.;Wang, S.;Klco, J. M.;Kaelin, W. G.;Livingston, D. M. Nat Med 2000, 6, 1335-1340.
17. O'Donnell, J. L.;Joyce, M. R.;Shannon, A. M.;Harmey, J.;Geraghty, J.;Bouchier-Hayes, D. Cancer Treat Rev 2006, 32, 407-416.
18. Newton, A. L.;Sharpe, B. K.;Kwan, A.;Mackay, J. P.;Crossley, M. J Biol Chem 2000, 275, 15128-15134.
19. Kung, A. L.;Zabludoff, S. D.;France, D. S.;Freedman, S. J.;Tanner, E. A.;Vieira, A.;Cornell-Kennon, S.;Lee, J.;Wang, B. Q.;Wang, J. M.;Memmert, K.;Naegeli, H. U.;Petersen, F.;Eck, M. J.;Bair, K. W.;Wood, A. W.;Livingston, D. M. Cancer Cell 2004, 6, 33-43.
20. Freedman, S. J.;Sun, Z. Y. J.;Poy, F.;Kung, A. L.;Livingston, D. M.;Wagner, G.;Eck, M. J. Proc Natl Acad Sci USA 2002, 99, 5367-5372.
21. Takahashi, C.;Numata, A.;Matsumura, E.;Minoura, K.;Eto, H.;Shingu, T.;Ito, T.;Hasegawa, T. J Antibiot 1994, 47, 1242-1249.
22. Waksman, S. A.;Bugie, E. J Bacteriol 1944, 48, 527-530.
23. Block, K. M.;Wang, H.;Szabo, L. Z.;Polaske, N. W.;Henchey, L. K.;Dubey, R.;Kushal, S.;Laszlo, C. F.;Makhoul, J.;Song, Z. H.;Meuillet, E. J.;Olenyuk, B. Z. J Am Chem Soc 2009, 131, 18078-18088.
24. Cook, K. M.;Hilton, S. T.;Mecinovic, J.;Motherwell, W. B.;Figg, W. D.;Schofield, C. J. J Biol Chem 2009, 284, 26831-26838.
25. Ottenheijm, H. C. J.;Herscheid, J. D. M.;Tijhuis, M. W.;Nivard, R. J. F.;Declercq, E.;Prick, P. A. J. J Med Chem 1978, 21, 799-804.
26. Freedman, S. J.;Sun, Z. Y. J.;Kung, A. L.;France, D. S.;Wagner, G.;Eck, M. J. Nat Struct Biol 2003, 10, 504-512.
27. Fukuyama, T.;Nakatsuka, S.;Kishi, Y. Tetrahedron 1981, 37, 2045-2078.
28. Roehrl, M. H. A.;Wang, J. Y.;Wagner, G. Biochemistry 2004, 43, 16056-16066.
29. Ottenheijm, H. C. J.;Herscheid, J. D. M.;Kerkhoff, G. P. C.;Spande, T. F. J Org Chem 1976, 41, 3433-3438.
30. Ottenheijm, H. C. J.;Kerkhoff, G. P. C.;Bijen, J.;Spande, T. F. J Chem Soc Chem Commun 1975, 768-769.
31. Hino, T.;Sato, T. Chem Pharm Bull 1974, 22, 2866-2874.
32. Dong, J. Y.;He, H. P.;Shen, Y. M.;Zhang, K. Q. J Nat Prod 2005, 68, 1510-1513.
33. Poisel, H.;Schmidt, U. Angew Chem Int Ed 1971, 10, 130.
34. Schmidt, U.;Hausler, J.;Ohler, E.;Poisel, H. Chem Ber Recl 1977, 110, 3722-3723.
35. Hino, T.;Sato, T. Tetrahedron Lett 1971, 3127.
36. Bernardo, P. H.;Brasch, N.;Chai, C. L. L.;Waring, P. J Biol Chem 2003, 278, 46549-46555.
37. Shibata, T.;Giaccia, A. J.;Brown, J. M. Gene Ther 2000, 7, 493-498.
38. Olenyuk, B. Z.;Zhang, G. J.;Klco, J. M.;Nickols, N. G.;Kaelin, W. G.;Dervan, P. B. Proc Natl Acad Sci USA 2004, 101, 16768-16773.
39. Lee, L. W.;Taylor, C. E. C.;Desaulniers, J. P.;Zhang, M. C.;Hojfeldt, J. W.;Pan, Q.;Mapp, A. K. Bioorg Med Chem Lett 2009, 19, 6233-6236.
40. Lum, J. K.;Wu, Z. Q.;Mapp, A. K. ChemBioChem 2007, 8, 1233-1236.
41. Dervan, P. B.;Poulin-Kerstien, A. T.;Fechter, E. J.;Edelson, B. S. In Waring, M. J.; Chaires, J. B. (eds) DNA Binders and Related Subjects; Springer-Verlag: Berlin, 2005; pp 1-31.
42. Doss, R. M.;Marques, M. A.;Foister, S.;Chenoweth, D. M.;Dervan, P. B. J Am Chem Soc 2006, 128, 9074-9079.
43. Nickols, N. G.;Dervan, P. B. Proc Natl Acad Sci USA 2007, 104, 10418-10423.
44. Nickols, N. G.;Jacobs, C. S.;Farkas, M. E.;Dervan, P. B. ACS Chem Biol 2007, 2, 561-571.
45. Lee, L. W.;Mapp, A. K. J Biol Chem 2010, 285, 11033-11038.
46. Arndt, H. D. Angew Chem Int Ed 2006, 45, 4552-4560.
47. Henchey, L. K.;Kushal, S.;Dubey, R.;Chapman, R. N.;Olenyuk, B. Z.;Arora, P. S. J Am Chem Soc 2010, 132, 941-943.
48. Moellering, R. E.;Cornejo, M.;Davis, T. N.;Del Bianco, C.;Aster, J. C.;Blacklow, S. C.;Kung, A. L.;Gilliland, D. G.;Verdine, G. L.;Bradner, J. E. Nature 2009, 462, 182-188.
49. Ferrara, N.;Mass, R. D.;Campa, C.;Kim, R. Annu Rev Med 2007, 58, 491-504.