Cytotoxic 3,6-bis((imidazolidinone)imino)acridines: Synthesis, DNA binding and molecular modeling

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 5, 2011, Pages 1790-1801

  Janovec, Ladislav ^a   Kožurková, Mária ^a   Sabolová, Danica ^a   Ungvarský, Ján ^a   Paulíková, Helena ^b   Plšíková, Jana ^a   Vantová, Zuzana ^b   Imrich, Ján ^a  

^a P J AFÁRIK UNIVERSITY   (Slovakia)

^b SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

Author keywords

Antitumor; DNA intercalation; Modeling; Proflavine; Topoisomerase

Indexed keywords

3,6 BIS[(1 N HEXYL 5 OXOIMIDAZOLIDIN 2 YLIDEN)IMINO]ACRIDINE; ACRIDINE DERIVATIVE; ANTINEOPLASTIC AGENT; DNA; DNA TOPOISOMERASE; IMIDAZOLIDINE DERIVATIVE; INTERCALATING AGENT; LIGAND; UNCLASSIFIED DRUG;

AGAR GEL ELECTROPHORESIS; ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL LINE; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CONTROLLED STUDY; CYTOTOXICITY; DNA BINDING; DRUG TARGETING; FLUORESCENCE SPECTROSCOPY; HELA CELL; HUMAN; HUMAN CELL; LEUKEMIA CELL; MOLECULAR DYNAMICS; MOLECULAR MODEL; MOUSE; NONHUMAN; PARTITION COEFFICIENT; PROMYELOCYTIC LEUKEMIA; SPECTROFLUOROMETRY; THYMUS; ULTRAVIOLET SPECTROSCOPY;

ACRIDINES; ANIMALS; CELL LINE, TUMOR; CIRCULAR DICHROISM; DNA TOPOISOMERASES, TYPE I; ENZYME INHIBITORS; HUMANS; IMIDAZOLIDINES; MICE; MODELS, MOLECULAR; MOLECULAR DYNAMICS SIMULATION; MOLECULAR STRUCTURE; THERMODYNAMICS;

EID: 79952189620     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.01.012     Document Type: Article

References (38)

1. W.A. Denny Curr. Med. Chem. 8 2001 533
2. N. Kapuriya, K. Kapuriya, X. Zhang, T.-Ch. Chou, R. Kakadiya, Y.-T. Wu, T.-H. Tsai, Y.-T. Chen, T.-Ch. Lee, A. Shah, Y. Naliapara, and T.-L. Su Bioorg. Med. Chem. 16 2008 5413
3. N. Desbois, M. Gardette, J. Papon, P. Labarre, A. Maisonial, P. Auzeloux, C. Lartigue, B. Bouchon, E. Debiton, Y. Blache, O. Chavignon, J.-P. Teulade, J. Maublant, J.-P. Madelmont, N. Moins, and J.-M. Chezal Bioorg. Med. Chem. 16 2008 7671
4. L.M. Oppegard, A.V. Ougolkov, D.N. Luchini, R.A. Schoon, J.R. Goodell, H. Kaur, D.D. Billadeau, D.M. Ferguson, and H. Hiasa Eur. J. Pharmacol. 602 2009 223
5. P. Belmont, J. Bosson, T. Godet, and M. Tiano Anticancer Agents Med. Chem. 7 2007 139
6. V.A. Bacherikov, J.-Y. Chang, Y.-W. Lin, Ch.-H. Chen, W.-Y. Pan, H. Dong, R.-Z. Lee, T.-Ch. Chou, and T.-L. Su Bioorg. Med. Chem. 23 2005 6513
7. S. Vispé, I. Vandenberghe, and M. Robin Biochem. Pharmacol. 73 2007 1863
8. L. Janovec, D. Sabolová, M. Kožurková, H. Paulíková, P. Kristian, J. Ungvarský, E. Moravčíková, M. Bajdichová, D. Podhradský, and J. Imrich Bioconjug. Chem. 18 2007 93
9. R. Appel, R. Kleinstück, and K.D. Zien Chem. Ber. 104 1971 1335
10. D. Sabolová, M. Kožurková, P. Kristian, I. Danihel, D. Podhradský, and J. Imrich Int. J. Biol. Macromol. 38 2006 94
11. J. McGhee, and P. von Hippel J. Mol. Biol. 86 1974 469
12. T.C. Jenkins K.R. Fox, Methods in Molecular Biology Vol. 90 1997 Humana Press Totowa, New Jersey 195 218
13. M. Kožurková, D. Sabolová, L. Janovec, J. Mikeš, J. Kovaľ, J. Ungvarský, P. Fedoročko, P. Kristian, and J. Imrich Bioorg. Med. Chem. 16 2008 3976
14. Z. Vantová, H. Paulíková, D. Sabolová, M. Kožurková, M. Sucháňová, L. Janovec, P. Kristian, and J. Imrich Int. J. Biol. Macromol. 45 2009 174
15. M.R. Duff, W.B. Tan, A. Bhambhani, B.S. Perrin, J. Thota, A. Rodger, and C.V. Kumar J. Phys. Chem. B 110 2006 20693
16. A.K. McClendon, and N. Osheroff Mutat. Res. 623 2007 83
17. Y. Pommier, P. Pourquier, Y. Fan, and D. Stumberg Biochim. Biophys. Acta, Gene Struct. Expression 1400 1998 83
18. Y. Pommier Nat. Rev. Cancer 6 2006 789
19. S. Basili, G. Basso, A. Faccio, A. Granyhan, H. Ihmels, S. Moro, and G. Viola ChemMedChem 3 2008 1671
20. J.B. Chaires Biopolymers 44 1997 201
21. M.T. Record Jr., J.-H. Ha, and M.A. Fisher Methods Enzymol. 208 1991 291
22. J. Ren, T.C. Jenkins, and J.B. Chaires Biochemistry 39 2000 8439
23. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, and T.E. Ferrin J. Comput. Chem. 25 2004 1605
24. J. Buša Octave Vol. 1 2006 Technical University in Košice Košice
25. J. Carmichael, W.G. DeGraff, A.F. Gazdar, J.D. Minna, and J.B. Mitchell Cancer Res. 47 1987 936
26. http://www.chemaxon.com.
27. http://gabedit.sourceforge.net/.
28. M.W. Schmidt, K.K. Baldridge, J.A. Boatz, S.T. Elbert, M.S. Gordon, J.H. Jensen, S. Koseki, N. Matsunaga, K.A. Nguyen, S.J. Su, T.L. Windus, M. Dupuis, and J.A. Montgomery J. Comput. Chem. 14 1993 1347
29. J.C. Phillips, R. Braun, W. Wang, J. Gumbart, E. Tajkhorshid, E. Villa, C. Chipot, R.D. Skeel, L. Kale, and K. Schulten J. Comput. Chem. 26 2005 1781
30. W.L. Jorgensen, J. Chandrasekhar, J. Madura, and M.L. Klein J. Chem. Phys. 79 1983 926
31. J. Wang, P. Cieplak, and P.A. Kollman J. Comput. Chem. 21 2000 1049
32. J. Wang, W. Wang, P.A. Kollman, and D.A. Case J. Mol. Graphics Modell. 25 2006 247
33. J. Wang, R.M. Wolf, J.W. Caldwell, P.A. Kollman, and D.A. Case J. Comput. Chem. 25 2004 1157
34. T. Darden, D. York, and L. Pedersen J. Chem. Phys. 98 1993 10089
35. R. Huey, G.M. Morris, A.J. Olson, and D.S. Goodsell J. Comput. Chem. 28 2007 1145
36. G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, and A.J. Olson J. Comput. Chem. 19 1998 1639
37. M.F. Sanner J. Mol. Graphics Modell. 17 1999 57
38. W.F. Humphrey, A. Dalke, and K. Schulten J. Mol. Graphics 14 1996 33