The discovery and optimization of novel dual inhibitors of topoisomerase ii and histone deacetylase

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 22, 2013, Pages 6981-6995

  Zhang, Xuan ^a   Bao, Bin ^a   Yu, Xiuhua ^a   Tong, Linjiang ^b   Luo, Yu ^a   Huang, Qingqing ^a   Su, Mingbo ^b   Sheng, Li ^b   Li, Jia ^b   Zhu, Hong ^c   Yang, Bo ^c   Zhang, Xiongwen ^a   Chen, Yi ^b   Lu, Wei ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^c ZHEJIANG UNIVERSITY   (China)

Author keywords

Cancer; HDAC; Hybrid; Podophyllotoxin; Synergistic effect; Topoisomerase II

Indexed keywords

GYRASE INHIBITOR; HISTONE DEACETYLASE INHIBITOR; PODOPHYLLOTOXIN DERIVATIVE; VORINOSTAT;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL STRAIN HCT116; CHEMICAL MODIFICATION; COLON CARCINOMA; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG POTENCY; DRUG RESEARCH; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; GROWTH INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; NONHUMAN; PROCESS OPTIMIZATION; STRUCTURE ACTIVITY RELATION;

CANCER; HDAC; HYBRID; PODOPHYLLOTOXIN; SYNERGISTIC EFFECT; TOPOISOMERASE II;

DNA TOPOISOMERASES, TYPE II; DRUG EVALUATION, PRECLINICAL; ENZYME ACTIVATION; HCT116 CELLS; HISTONE DEACETYLASE INHIBITORS; HISTONE DEACETYLASES; HUMANS; HYDROXAMIC ACIDS; PHENYLENEDIAMINES; PODOPHYLLOTOXIN; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; TOPOISOMERASE II INHIBITORS;

EID: 84885858940     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.09.023     Document Type: Article

References (49)

1. E.R. Fearon, and B. Vogelstein Cell 61 1990 759
2. L. Costantino, and D. Barlocco Future Med. Chem. 5 2013 5
3. M.S. Kim, M. Blake, J.H. Baek, G. Kohlhagen, Y. Pommier, and F. Carrier Cancer Res. 63 2003 7291
4. F. Bruzzese, M. Rocco, S. Castelli, E. Di Gennaro, A. Desideri, and A. Budillon Mol. Cancer Ther. 8 2009 3075
5. R.L. Bevins, and S.G. Zimmer Cancer Res. 65 2005 6957
6. M. Ocker, A. Alajati, M. Ganslmayer, S. Zopf, M. Luders, D. Neureiter, E.G. Hahn, D. Schuppan, and C. Herold J. Cancer Res. Clin. Oncol. 131 2005 385
7. B. Sarcar, S. Kahali, and P. Chinnaiyan J. Neurooncol. 99 2010 201
8. M. Dokmanovic, C. Clarke, and P.A. Marks Mol. Cancer Res. 5 2007 981
9. H.Y. Lin, C.S. Chen, S.P. Lin, J.R. Weng, and C.S. Chen Med. Res. Rev. 26 2006 397
10. M.J. Lee, Y.S. Kim, S. Kummar, G. Giaccone, and J.B. Trepel Curr. Opin. Oncol. 20 2008 639
11. C.S. Chen, S.C. Weng, P.H. Tseng, H.P. Lin, and C.S. Chen J. Biol. Chem. 280 2005 38879
12. A. Saito, T. Yamashita, Y. Mariko, Y. Nosaka, K. Tsuchiya, T. Ando, T. Suzuki, T. Tsuruo, and O. Nakanishi Proc. Natl. Acad. Sci. U.S.A. 96 1999 4592
13. R.D. Glick, S.L. Swendeman, D.C. Coffey, R.A. Rifkind, P.A. Marks, V.M. Richon, and MP La Quaglia Cancer Res. 59 1999 4392
14. L.M. Butler, D.B. Agus, H.I. Scher, B. Higgins, A. Rose, C. Cordon-Cardo, H.T. Thaler, R.A. Rifkind, P.A. Marks, and V.M. Richon Cancer Res. 60 2000 5165
15. A.K. Oyelere, P.C. Chen, W. Guerrant, S.C. Mwakwari, R. Hood, Y. Zhang, and Y. Fan J. Med. Chem. 52 2009 456
16. B.S. Mann, J.R. Johnson, M.H. Cohen, R. Justice, and R. Pazdur Oncologist 12 2007 1247
17. C. Grant, F. Rahman, R. Piekarz, C. Peer, R. Frye, R.W. Robey, E.R. Gardner, W.D. Figg, and S.E. Bates Expert Rev. Anticancer Ther. 10 2010 997
18. S.C. Mwakwari, V. Patil, W. Guerrant, and A.K. Oyelere Curr. Top. Med. Chem. 10 2010 1423
19. X. Cai, H.X. Zhai, J. Wang, J. Forrester, H. Qu, L. Yin, C.J. Lai, R. Bao, and C. Qian J. Med. Chem. 2010 2000 53
20. C.J. Lai, R. Bao, X. Tao, J. Wang, R. Atoyan, H. Qu, D.G. Wang, L. Yin, M. Samson, J. Forrester, B. Zifcak, G.X. Xu, S. DellaRocca, H.X. Zhai, X. Cai, W.E. Munger, M. Keegan, C.V. Pepicelli, and C. Qian Cancer Res. 70 2010 3647
21. S. Mahboobi, S. Dove, A. Sellmer, M. Winkler, E. Eichhorn, H. Pongratz, T. Ciossek, T. Baer, T. Maier, and T. Beckers J. Med. Chem. 52 2009 2265
22. S. Mahboobi, A. Sellmer, M. Winkler, E. Eichhorn, H. Pongratz, T. Ciossek, T. Baer, T. Maier, and T. Beckers J. Med. Chem. 53 2010 8546
23. F. Thaler Pharm. Pat. Analyst 1 2012 75
24. X. Zhang, J. Zhang, L. Tong, Y. Luo, M. Su, Y. Zang, J. Li, W. Lu, and Y. Chen Bioorg. Med. Chem. 21 2013 3240
25. X. Zhang, M. Su, Y. Chen, J. Li, and W. Lu Molecules 18 2013 6491
26. B.E. Gryder, M.K. Rood, K.A. Johnson, V. Patil, E.D. Raftery, L.-P.D. Yao, M. Rice, B. Azizi, D.F. Doyle, and A.K. Oyelere J. Med. Chem. 56 2013 5782
27. K.S. Ko, M.E. Steffey, K.R. Brandvold, and M.B. Soellner ACS Med. Chem. Lett. 4 2013 779
28. L.F. Liu Annu. Rev. Biochem. 58 1989 351
29. D. Xu, J. Cao, S. Qian, L. Li, C. Hu, Q. Weng, J. Lou, D. Zhu, H. Zhu, Y. Hu, Q. He, and B. Yang Invest. New Drugs 29 2011 786
30. C. Hu, D. Xu, W. Du, S. Qian, L. Wang, J. Lou, Q. He, B. Yang, and Y. Hu Mol. Biosyst. 6 2010 410
31. X.C. Yang, S.J. Qian, L. Wang, S.D. Liao, J. Cao, Y.Z. Hu, Q.J. He, H. Zhu, and B. Yang Transl. Oncol. 6 2013 75
32. K.R. Hande Eur. J. Cancer 34 1998 1514
33. K.R. Hande Bba-Gene Struct. Expr. 1400 1998 173
34. M.G. Catalano, N. Fortunati, M. Pugliese, R. Poli, O. Bosco, R. Mastrocola, M. Aragno, and G. Boccuzzi J. Endocrinol. 191 2006 465
35. W. Guerrant, V. Patil, J.C. Canzoneri, and A.K. Oyelere J. Med. Chem. 55 2012 1465
36. W. Guerrant, V. Patil, J.C. Canzoneri, L.P. Yao, R. Hood, and A.K. Oyelere Bioorg. Med. Chem. Lett. 23 2013 3283
37. B.H. Long, S.T. Musial, and M.G. Brattain Biochemistry 23 1984 1183
38. Z.Q. Wang, Y.H. Kuo, D. Schnur, J.P. Bowen, S.Y. Liu, F.S. Han, J.Y. Chang, Y.C. Cheng, and K.H. Lee J. Med. Chem. 33 1990 2660
39. Y.L. Zhang, X. Guo, Y.C. Cheng, and K.H. Lee J. Med. Chem. 37 1994 446
40. X.K. Zhu, J. Guan, Y. Tachibana, K.F. Bastow, S.J. Cho, H.H. Cheng, Y.C. Cheng, M. Gurwith, and K.H. Lee J. Med. Chem. 42 1999 2441
41. Z. Xiao, K.F. Bastow, J.R. Vance, R.S. Sidwell, H.K. Wang, M.S. Chen, Q. Shi, and K.H. Lee J. Med. Chem. 47 2004 5140
42. J.M. Barret, A. Kruczynski, S. Vispe, J.P. Annereau, V. Brel, Y. Guminski, J.G. Delcros, A. Lansiaux, N. Guilbaud, T. Imbert, and C. Bailly Cancer Res. 68 2008 9845
43. A. Kamal, P. Suresh, M.J. Ramaiah, T. Srinivasareddy, R.K. Kapavarapu, B.N. Rao, S. Imthiajali, T. Lakshminarayanreddy, S.N.C.V.L Pushpavalli, N. Shankaraiah, and M. Pal-Bhadra Bioorg. Med. Chem. 21 2013 5198
44. Y.-F. Chen, Y.-C. Lin, P.-K. Huang, H.-C. Chan, S.-C. Kuo, K.-H. Lee, and L.-J. Huang Bioorg. Med. Chem. 21 2013 5064
45. L. Wang, F. Yang, X. Yang, X. Guan, C. Hu, T. Liu, Q. He, B. Yang, and Y. Hu Eur. J. Med. Chem. 46 2011 285
46. J.M. Altenburger, C. Mioskowski, H. Dorchymont, D. Schirlin, C. Schalk, and C. Tarnus Tetrahedron Lett. 33 1992 5055
47. M.S. Finnin, J.R. Donigian, A. Cohen, V.M. Richon, R.A. Rifkind, P.A. Marks, R. Breslow, and N.P. Pavletich Nature 401 1999 188
48. A. Vasudevan, Z. Ji, R.R. Frey, C.K. Wada, D. Steinman, H.R. Heyman, Y. Guo, M.L. Curtin, J. Guo, J. Li, L. Pease, K.B. Glaser, P.A. Marcotte, J.J. Bouska, S.K. Davidsen, and M.R. Michaelides Bioorg. Med. Chem. Lett. 13 2003 3909
49. K.B. Glaser, J. Li, M.E. Aakre, D.W. Morgan, G. Sheppard, K.D. Stewart, J. Pollock, P. Lee, C.Z. O'Connor, S.N. Anderson, D.J. Mussatto, C.W. Wegner, and H.L. Moses Mol. Cancer. Ther. 1 2002 759