Synthesis and biological evaluation of 2,4-diaminoquinazoline derivatives as novel heat shock protein 90 inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 6, 2011, Pages 1593-1597

  Thorat, Dhanaji Achyutrao ^a,c   Doddareddy, Munikumar Reddy ^a,c   Seo, Seon Hee ^a   Hong, Tae Joon ^b   Cho, Yong Seo ^a   Hahn, Ji Sook ^b   Pae, Ae Nim ^a  

^a Korea Institute of Science and Technology   (South Korea)

^b Seoul National University   (South Korea)

^c University of Science and Technology (UST)   (South Korea)

Author keywords

2,4 Diaminoquinazolines; Cancer; Hsp90 inhibitors

Indexed keywords

2,4 DIAMINOQUINAZOLINE DERIVATIVE; EPIDERMAL GROWTH FACTOR RECEPTOR 2; HEAT SHOCK PROTEIN 70; HEAT SHOCK PROTEIN 90 INHIBITOR;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CELL STRAIN HCT116; CELL STRAIN HT29; CELL STRAIN MCF 7; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; PROTEIN EXPRESSION; PROTEIN INDUCTION; STRUCTURE ACTIVITY RELATION;

CELL LINE, TUMOR; CELL PROLIFERATION; DRUG EVALUATION, PRECLINICAL; HSP90 HEAT-SHOCK PROTEINS; HUMANS; QUINAZOLINES;

EID: 79952364637     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.01.117     Document Type: Article

References (28)

1. H. Zhang, and F. Burrows J. Mol. Med. 82 2004 488
2. J.S. Isaacs, W. Xu, and L. Neckers Cancer Cell 2003 213
3. D.D. Mosser, and R.I. Morimotto Oncogene 23 2004 2907
4. G. Chiosis Expert Opin. Ther. Targets 2006 10 37
5. M. Yamakazi, K. Akaogi, T. Miwa, T. Imai, E. Soeda, and K. Yokoyama Nucleic Acid Res. 17 1989 7108
6. N. Rebbe, J. Ware, R.M. Bertina, P. Modric, and D.W. Staford Gene 53 1987 235
7. C. Prodromou, and L.H. Pearl Curr. Cancer Drug Targets 3 2003 301
8. A. Maloney, and P. Workman Expert Opin. Emerg. Drugs 1 2005 137
9. A. Maloney, and P. Workman Expert Opin. Biol. Ther. 2 2002 3
10. D.B. Solit, H.I. Scher, and N. Rosen Semin. Oncol. 30 2003 709
11. J. Beliakoff, and R. Begatell Clin. Cancer Res. 9 2003 4961
12. P. Connel, C.A. Ballinger, and J. Jiang Nat. Cell Biol. 3 2001 93
13. R.C. Chnur, and M.L. Corman J. Org. Chem. 59 1994 2581
14. L. Whitesell, E.G. Mimnaugh, B. De Costa, C.E. Myers, and L.M. Neckers Proc. Natl. Acad. Sci. 91 1994 8324
15. E.G. Mimnaugh, C. Chavany, and L. Neckers J. Biol. Chem. 271 1996 22796
16. S.M. Roe, C. Prodromou, R. O'Brien, J.E. Ladbury, P.W. Piper, and L.H. Pearl J. Med. Chem. 42 1999 260
17. A. Gopalsamy, M. Shi, J. Golas, E. Vogan, J. Jacob, M. Johnson, F. Lee, R. Nilakantan, R. Peterson, K. Svenson, and F. Boshcelli J. Med. Chem. 51 2008 373
18. H. Park, Y.J. Kim, and J. Hahn Biorg. Med. Chem. Lett. 2007 17 2007 6345
19. M. Vilenchik, D. Solit, A. Basso, H. Huezo, B. Lucas, H. He, N. Rosen, C. Spampinato, P. Modrich, and G. Chiosis Chem. Biol. 11 2004 787
20. Doddareddy, M. R.; Thorat, D. A.; Seo, S. H.; Hong, T.-J.; Cho, Y. S.; Hahn, J.-S.; Pae, A. N. Bioorg. Med. Chem. 2011, doi:10.1016/j.bmc.2011.01.023.
21. F. Godde, J.-J. Toulmé, and S. Moreau Biochemistry 37 1998 13765
22. K. Kosuke, and O. Katsunori Bioorg. Med. Chem. 14 10 2006 3307
23. N. Sirisoma, and S. Kasibhatla J. Med. Chem. 51 15 2008 4771
24. +.
25. M.N. Jo, H.J. Seo, Y. Kim, S.H. Seo, H. Rhim, Y.S. Cho, J.H. Cha, H.Y. Koh, H. Choo, and A.N. Pae Bioorg. Med. Chem. 15 2007 365
26. 50.
27. 5 cells/well and grown up to 60% confluency. Grown cells were treated with the compounds, 17-AAG which was dissolved in DMSO, or DMSO alone as a control. Cells were incubated for an additional 24 h and then harvested and lysed in TNES buffer [50 mM Tris-HCl, pH 7.4, 1% NP-40, 2 mM EDTA, 100 mM NaCl, 1 mM PMSF, 0.1% protease inhibitor cocktail solution]. The clarified cell lysates were collected after centrifugation and the protein concentration of each lysates were determined by Protein assay solution (Bio-rad). Each lysates containing 50 μg of total protein was loaded, subjected to SDS-PAGE and transferred to nitrocellulose membrane. After being probed with an antibody against Her2-neu (Santa Cruz Biotechnology), the membrane was stripped and also probed with antibodies against β-tubulin (Santa Cruz Biotechnology) and HSP70 (Stressgen Bioreagents).
28. J. Zou, Y. Guo, T. Guettouche, D.F. Smith, and R. Voellmy Cell 94 1998 471