Journal of the American Chemical Society
Article
Blankenfeldt, W.; Alexandrov, K.; Waldmann, H. Angew. Chem., Int. Ed.
2008, 47, 3747−3750.
(10) McKenna, C. E.; Kashemirov, B. A.; Blazewska, K. M.; Mallard-
Favier, I.; Stewart, C. A.; Rojas, J.; Lundy, M. W.; Ebetino, F. H.;
Baron, R. A.; Dunford, J. E.; Kirsten, M. L.; Seabra, M. C.; Bala, J. L.;
Marma, M. S.; Rogers, M. J.; Coxon, F. P. J. Med. Chem. 2010, 53,
3454−3464.
(11) Tan, K. T.; Guiu-Rozas, E.; Bon, R. S.; Guo, Z.; Delon, C.;
Wetzel, S.; Arndt, S.; Alexandrov, K.; Waldmann, H.; Goody, R. S.;
Wu, Y. W.; Blankenfeldt, W. J. Med. Chem. 2009, 52, 8025−8037.
(12) Watanabe, M.; Fiji, H. D.; Guo, L.; Chan, L.; Kinderman, S. S.;
Slamon, D. J.; Kwon, O.; Tamanoi, F. J. Biol. Chem. 2008, 283, 9571−
9579.
ASSOCIATED CONTENT
* Supporting Information
Full experimental detail, synthesis and characterization of
compounds, ESI-MS measurements of covalent modifications,
X-ray data collection, and refinement statistics, and |FOFC|
difference electron density map. This material is available free
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AUTHOR INFORMATION
Corresponding Author
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Present Addresses
(13) Wu, Y. W.; Waldmann, H.; Reents, R.; Ebetino, F. H.; Goody, R.
S.; Alexandrova, K. ChemBioChem 2006, 7, 1859−1861.
(14) Wu, Y. W.; Alexandrov, K.; Brunsveld, L. Nat. Protoc. 2007, 2,
2704−2711.
#Institute for Molecular Bioscience The University of Queens-
land, Brisbane, 306 Carmody Road, St Lucia, QLD,
4072, Australia
○Lehrstuhl fur Biochemie, Universitat Bayreuth, Uni-
(15) Neamati, N.; Hong, H.; Mazumder, A.; Wang, S.; Sunder, S.;
Nicklaus, M. C.; Milne, G. W.; Proksa, B.; Pommier, Y. J. Med. Chem.
1997, 40, 942−951.
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versitatsstraße 30, 95447 Bayreuth, Germany
̈
◆School of Chemistry and Biomedical and Health Research
Centre, University of Leeds, Leeds, LS2 9JT, United Kingdom
¶Laboratoire de Chimie de Coordination du CNRS, 205 route
de Narbonne, 31077 Toulouse, France
(16) Hidalgo, M. E.; Fernandez, E.; Quilhot, W.; Lissi, E.
Phytochemistry 1994, 37, 1585−1587.
(17) Muller, K. Appl. Microbiol. Biotechnol. 2001, 56, 9−16.
(18) Correche, E. R.; Enriz, R. D.; Piovano, M.; Garbarino, J.;
Gomez-Lechon, M. J. Altern. Lab Anim. 2004, 32, 605−615.
(19) Sala, T.; Sargent, M. V. J. Chem. Soc., Perkin Trans. 1 1979,
2593−2598.
Author Contributions
⊥These authors contributed equally.
Notes
(20) Kulkarni, N. N.; Kulkarni, V. S.; Lele, S. R.; Hosangadi, B. D.
Tetrahedron 1988, 44, 5145−5149.
The authors declare no competing financial interest.
(21) Guo, Z.; Wu, Y. W.; Das, D.; Delon, C.; Cramer, J.; Yu, S.;
Thuns, S.; Lupilova, N.; Waldmann, H.; Brunsveld, L.; Goody, R. S.;
Alexandrov, K.; Blankenfeldt, W. EMBO J. 2008, 27, 2444−2456.
(22) Zhang, H.; Seabra, M. C.; Deisenhofer, J. Structure 2000, 8,
241−251.
ACKNOWLEDGMENTS
This work was supported by the Deutsche Forschungsgemein-
schaft, the Max-Planck-Gesellschaft, and the Zentrum fur
Angewandte Chemische Genomik. C.D. and R.S.B. thank the
Alexander von Humboldt-Stiftung for fellowships. We thank
the X-ray communities of the Max Planck Institute of
Molecular Physiology (Dortmund, Germany) and the Max
Planck Institute of Medical Research (Heidelberg, Germany)
for collecting diffraction data at the Swiss Light Source of the
Paul Scherrer Institute (Villigen, Switzerland) and for giving us
generous access to and support for station X10SA.
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(23) Lane, K. T.; Beese, L. S. J. Lipid Res. 2006, 47, 681−699.
REFERENCES
■
(1) Konstantinopoulos, P. A.; Karamouzis, M. V.; Papavassiliou, A. G.
Nat. Rev. Drug Discovery 2007, 6, 541−555.
(2) Stenmark, H. Nat. Rev. Mol. Cell Biol. 2009, 10, 513−525.
(3) Coxon, F. P.; Helfrich, M. H.; Larijani, B.; Muzylak, M.; Dunford,
J. E.; Marshall, D.; McKinnon, A. D.; Nesbitt, S. A.; Horton, M. A.;
Seabra, M. C.; Ebetino, F. H.; Rogers, M. J. J. Biol. Chem. 2001, 276,
48213−48222.
(4) Roelofs, A. J.; Hulley, P. A.; Meijer, A.; Ebetino, F. H.; Russell, R.
G.; Shipman, C. M. Int. J. Cancer 2006, 119, 1254−1261.
(5) Lackner, M. R.; Kindt, R. M.; Carroll, P. M.; Brown, K.; Cancilla,
M. R.; Chen, C.; de, S. H.; Franke, Y.; Guan, B.; Heuer, T.; Hung, T.;
Keegan, K.; Lee, J. M.; Manne, V.; O’Brien, C.; Parry, D.; Perez-Villar,
J. J.; Reddy, R. K.; Xiao, H.; Zhan, H.; Cockett, M.; Plowman, G.;
Fitzgerald, K.; Costa, M.; Ross-Macdonald, P. Cancer Cell 2005, 7,
325−336.
(6) Mitra, S.; Cheng, K. W.; Mills, G. B. Semin. Cell Dev. Biol. 2011,
22, 57−68.
(7) Cheng, K. W.; Lahad, J. P.; Kuo, W. L.; Lapuk, A.; Yamada, K.;
Auersperg, N.; Liu, J.; Smith-McCune, K.; Lu, K. H.; Fishman, D.;
Gray, J. W.; Mills, G. B. Nat. Med. 2004, 10, 1251−1256.
(8) Bon, R. S.; Guo, Z.; Stigter, E. A.; Wetzel, S.; Menninger, S.;
Wolf, A.; Choidas, A.; Alexandrov, K.; Blankenfeldt, W.; Goody, R. S.;
Waldmann, H. Angew. Chem., Int. Ed. 2011, 50, 4957−4961.
(9) Guo, Z.; Wu, Y. W.; Tan, K. T.; Bon, R. S.; Guiu-Rozas, E.;
Delon, C.; Nguyen, T. U.; Wetzel, S.; Arndt, S.; Goody, R. S.;
7391
dx.doi.org/10.1021/ja211305j | J. Am. Chem. Soc. 2012, 134, 7384−7391