Structural basis of the antiproliferative activity of largazole, a depsipeptide inhibitor of the histone deacetylases

Journal of the American Chemical Society

Volumn 133, Issue 32, 2011, Pages 12474-12477

  Cole, Kathryn E ^a   Dowling, Daniel P ^a   Boone, Matthew A ^b   Phillips, Andrew J ^b   Christianson, David W ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIPROLIFERATIVE ACTIVITIES; ANTIPROLIFERATIVE EFFECT; CANCER CHEMOTHERAPY; CHEMICAL FEATURES; COORDINATION GEOMETRY; CORE STRUCTURE; FLORIDA; HDAC INHIBITORS; HISTONE DEACETYLASES; IN-VIVO; MACROCYCLICS; MARINE CYANOBACTERIUM; MODE OF ACTION; NATURAL PRODUCTS; POTENT INHIBITOR; RING SYSTEMS; SIDE-CHAINS; STRUCTURAL BASIS; THIOESTERS; THIOL COMPLEXES;

CHEMOTHERAPY; COORDINATION REACTIONS;

CRYSTAL STRUCTURE;

HISTONE DEACETYLASE INHIBITOR; LARGAZOLE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; CATALYSIS; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; DISULFIDE BOND; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROLYSIS; STRUCTURE ACTIVITY RELATION;

CRYSTALLOGRAPHY, X-RAY; CYANOBACTERIA; DEPSIPEPTIDES; HISTONE DEACETYLASE INHIBITORS; HISTONE DEACETYLASES; HUMANS; MODELS, MOLECULAR; REPRESSOR PROTEINS; THIAZOLES;

EID: 80051599485     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja205972n     Document Type: Article

References (26)

1. De Ruijter, A. J.; van Gennip, A. H.; Caron, H. N.; Kemp, S.; van Kuilenburg, A. B. Biochem. J. 2003, 370, 737-749
2. Haberland, M.; Montgomery, R. L.; Olson, E. N. Nat. Rev. Genet. 2009, 10, 32-42
3. Emanuele, S.; Lauricella, M.; Tesoriere, G. Int. J. Oncol. 2008, 33, 637-646
4. Gregoretti, I. V.; Lee, Y. M.; Goodson, H. V. J. Mol. Biol. 2004, 338, 17-31
5. Kanyo, Z. F.; Scolnick, L. R.; Ash, D. E.; Christianson, D. W. Nature 1996, 383, 554-557
6. Gantt, S. L.; Gattis, S. G.; Fierke, C. A. Biochemistry 2006, 45, 6170-6178
7. Mwakwari, S. C.; Patil, V.; Guerrant, W.; Oyelere, A. K. Curr. Top. Med. Chem. 2010, 10, 1423-1440
8. Marks, P. A.; Wu, W. S. J. Cell. Biochem. 2009, 107, 600-608
9. Lane, A. A.; Chabner, B. A. J. Clin. Oncol. 2009, 27, 5459-5468
10. Mei, S.; Ho, A. D.; Mahlknecht, U. Int. J. Oncol. 2004, 25, 1509-1519
11. Bolden, J. E.; Peart, M. J.; Johnstone, R. W. Nat. Rev. 2006, 5, 769-784
12. Holmes, M. A.; Matthews, B. W. Biochemistry 1981, 20, 6912-6920
13. Mann, B. S.; Johnson, J. R.; Cohen, M. H.; Justice, R.; Pazdur, R. Oncologist 2007, 12, 1247-1252
14. Guan, P.; Fang, H. Drug Discovery Ther. 2010, 4, 388-391
15. Furumai, R.; Matsuyama, A.; Kobashi, N.; Lee, K. H.; Nishiyama, M.; Nakajima, H.; Tanaka, A.; Komatsu, Y.; Nishino, N.; Yoshida, M.; Horinouchi, S. Cancer Res. 2002, 62, 4916-4921
16. Taori, K.; Paul, V. J.; Luesch, H. J. Am. Chem. Soc. 2008, 130, 1806-1807
17. Bowers, A. A.; West, N.; Newkirk, T. L.; Troutman-Youngman, A. E.; Schreiber, S. L.; Wiest, O.; Bradner, J. E.; Williams, R. M. Org. Lett. 2009, 11, 1301-1304
18. Ying, Y.; Taori, K.; Kim, H.; Hong, J.; Luesch, H. J. Am. Chem. Soc. 2008, 130, 8455-8459
19. Behar, M. Newsweek 2010, 156, 40-41
20. Seiser, T.; Kamena, F.; Cramer, N. Angew. Chem. 2008, 47, 6483-6485
21. Dowling, D. P.; Gantt, S. L.; Gattis, S. G.; Fierke, C. A.; Christianson, D. W. Biochemistry 2008, 47, 13554-13563
22. Vannini, A.; Volpari, C.; Gallinari, P.; Jones, P.; Mattu, M.; Carfí, A.; De Francesco, R.; Steinkühler, C.; Di Marco, S. EMBO Rep. 2007, 8, 879-884
23. Chakrabarti, P. Biochemistry 1989, 28, 6081-6085
24. Zeng, X.; Yin, B.; Hu, Z.; Liao, C.; Liu, J.; Li, S.; Li, Z.; Nicklaus, M. C.; Zhou, G.; Jiang, S. Org. Lett. 2010, 12, 1368-1371
25. Ying, Y.; Liu, Y.; Byeon, S. R.; Kim, H.; Luesch, H.; Hong, J. Org. Lett. 2008, 10, 4021-4024
26. Benelkebir, H.; Marie, S.; Hayden, A. L.; Lyle, J.; Loadman, P. M.; Crabb, S. J.; Packham, G.; Ganesan, A. Bioorg. Med. Chem. 2011, 15, 3650-3658