Diarylmethyloxime and hydrazone derivatives with 5-indolyl moieties as potent inhibitors of tubulin polymerization

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 11, 2008, Pages 5952-5961

  Álvarez, Concepción ^a   Álvarez, Raquel ^a   Corchete, Purificación ^a   López, José Luis ^a   Pérez Melero, Concepción ^a   Peláez, Rafael ^a   Medarde, Manuel ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Antitumour; Combretastatin; Cytotoxicity; Hydrazide; Hydrazone; Indole; Oxime; Phenstatin; Tubulin

Indexed keywords

COLCHICINE; COMBRETASTATIN A4; DIARYL KETONE; HYDRAZONE DERIVATIVE; IMINE; INDOLE DERIVATIVE; OXIME DERIVATIVE; PHENSTATIN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CHEMICAL MODIFICATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INHIBITION KINETICS; ISOMER; MICROTUBULE ASSEMBLY; STEREOCHEMISTRY; X RAY DIFFRACTION;

ANTINEOPLASTIC AGENTS; BENZOPHENONES; BIBENZYLS; HELA CELLS; HL-60 CELLS; HT29 CELLS; HUMANS; HYDRAZONES; INDOLES; OXIMES; PHOSPHORIC ACID ESTERS; STEREOISOMERISM; TUBULIN; TUBULIN MODULATORS;

EID: 44449096594     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.04.054     Document Type: Article

References (44)

1. In: Hyams J., and Lloyd C.W. (Eds). Microtubules (1994), Wiley-Liss, New York
2. Jordan M.A., and Wilson L. Nat. Rev. Cancer 4 (2004) 253-265
3. Honore S., Pasquier E., and Braguer D. Cell Mol. Life Sci. 62 (2005) 3039-3056
4. Islam M.N., and Iskander M.N. Mini-Rev. Med. Chem. 4 (2004) 1077-1104
5. Zefirova O.N., Diikov A.G., Zyk N.V., and Zefirov N.S. Russ. Chem. Bull. Int. Ed. 56 (2007) 680-688
6. Nguyen T.L., McGrath C., Hermone A.R., Burnett J.C., Zaharevitz D.W., Day B.W., Wipf P., Hamel E., and Gussio R. J. Med. Chem. 48 (2005) 6107-6116
7. Ravelli R.B., Gigant B., Curmi P.A., Jourdain I., Lachkar S., Sobel A., and Knossow M. Nature 428 (2004) 198-202
8. Lin C.M., Ho H.H., Pettit G.R., and Hamel E. Biochemistry 28 (1989) 6984-6991
9. Lippert III J.W. Bioorg. Med. Chem. 15 (2007) 605-615
10. Tron G.C., Pirali T., Sorba G., Pagliai F., Busacca S., and Genazzani A.A. J. Med. Chem. 49 (2006) 3033-3044
11. Maya A.B., Perez-Melero C., Mateo C., Alonso D., Fernandez J.L., Gajate C., Mollinedo F., Pelaez R., Caballero E., and Medarde M. J. Med. Chem. 48 (2005) 556-568
12. Cushman M., Nagarathnam D., Gopal D., He H.M., Lin C.M., and Hamel E. J. Med. Chem. 35 (1992) 2293-2306
13. Pettit G.R., Toki B., Herald D.L., Verdier-Pinard P., Boyd M.R., Hamel E., and Pettit R.K. J. Med. Chem. 41 (1998) 1688-1695
14. Pettit G.R., Grealish M.P., Herald D.L., Boyd M.R., Hamel E., and Pettit R.K. J. Med. Chem. 43 (2000) 2731-2737
15. Liou J.P., Chang C.W., Song J.S., Yang Y.N., Yeh C.F., Tseng H.Y., Lo Y.K., Chang Y.L., Chang C.M., and Hsieh H.P. J. Med. Chem. 45 (2002) 2556-2562
16. Liou J.P., Chang J.Y., Chang C.W., Chang C.Y., Mahindroo N., Kuo F.M., and Hsieh H.P. J. Med. Chem. 47 (2004) 2897-2905
17. Liou J.P., Chang Y.L., Kuo F.M., Chang C.W., Tseng H.Y., Wang C.C., Yang Y.N., Chang J.Y., Lee S.J., and Hsieh H.P. J. Med. Chem. 47 (2004) 4247-4257
18. Duan J.X., Cai X., Meng F., Lan L., Hart C., and Matteucci M. J. Med. Chem. 50 (2007) 1001-1006
19. Alvarez C., Alvarez R., Corchete P., Perez-Melero C., Pelaez R., and Medarde M. Bioorg. Med. Chem. Lett. 17 (2007) 3417-3420
20. Brancale A., and Silvestri R. Med. Res. Rev. 27 (2007) 209-238
21. Zhang Q., Peng Y., Wang X.I., Keenan S.M., Arora S., and Welsh W.J. J. Med. Chem. 50 (2007) 749-754
22. Hu L., Jiang J.-d., Qu J., Li Y., Jin J., Li Z.-r., and Boykin D.W. Bioorg. Med. Chem. Lett. 17 (2007) 3613-3617
23. Liou J.-P., Wu C.-Y., Hsieh H.-P., Chang C.-Y., Chen C.-M., Kuo C.-C., and Chang J.-Y. J. Med. Chem. 50 (2007) 4548-4552
24. Zhang Q., Peng Y., Wang X.I., Keenan S.M., Arora S., and Welsh W.J. J. Med. Chem. 50 (2007) 749-754
25. Gurjar M.K., Wakharkar R.D., Singh A.T., Jaggi M., Borate H.B., Shinde P.D., Verma R., Rajendran P., Dutt S., Singh G., Sanna V.K., Singh M.K., Srivastava S.K., Mahajan V.A., Jadhav V.H., Dutta K., Krishnan K., Chaudhary A., Agarwal S.K., Mukherjee R., and Burman A.C. J. Med. Chem. 50 (2007) 1744-1753
26. Maya A.B.S., Pérez-Melero C., Salvador N., Peláez R., Caballero E., and Medarde M. Bioorg. Med. Chem. 13 (2005) 2097-2107
27. For example, compare compound 25b versus 25g and 27d versus 28a, p 1702 in. Woods K.W., Li Q., Barr K.J., McCroskey R.W., Hannick S.M., Gherke L., Credo R.B., Hui Y.H., Marsh K., Warner R., Lee J.Y., Zielinski-Mozng N., Frost D., Rosenberg S.H., and Sham H.L. J. Med. Chem. 45 (2002) 1697-1711
28. Kumpulainen H., Mahonen N., Laitinen M.L., Jaurakkajarvi M., Raunio H., Juvonen R.O., Vepsalainen J., Jarvinen T., and Rautio J. J. Med. Chem. 49 (2006) 1207-1211
29. Sotriffer C.A., and Dramburg I. J. Med. Chem. 48 (2005) 3122-3125
30. Ragno R., Frasca S., Manetti F., Brizzi A., and Massa S. J. Med. Chem. 48 (2005) 200-212
31. Zentgraf M., Fokkens J., and Sotriffer C.A. ChemMedChem 1 (2006) 1355-1359
32. version 1.27 was used. Jain A.N. J. Med. Chem. 46 (2003) 499-511
33. Jain, A. N. Surflex-Dock 2.1: J. Comput. Aided Mol. Des. 2007, 21, 281-306.
34. Shelanski M.L., Gaskin F., and Cantor C.R. Proc. Natl. Acad. Sci. U.S.A. 70 (1973) 765-768
35. Dumortier C., Gorbunoff M., Andreu J.M., and Engelborghs Y. Biochemistry 35 (1996) 4387-4395
36. Bradford M.M. Anal. Biochem. 72 (1976) 248-254
37. Han Y., Chaudhary A.G., Chordia M.D., Sackett D.L., Perez-Ramirez B., Kingston D.G., and Bane S. Biochemistry 35 (1996) 14173-14183
38. Pelaez R., López J.L., and Medarde M. Application of Chemoinformatic Tools for the Analysis of Virtual Screening Studies of Tubulin Inhibitors. In: Corchado E., Corchado J.M., and Abraham A. (Eds). Advances in Soft Computing Vol. 44 (2007), Springer-Verlag, Berlin 411-417
39. http://www.wwpdb.org/.
40. Discover program from http://www.accelrys.com/ was used.
41. Guex, N.; Peitsch, M. C. Electrophoresis 1997, 18, 2714-2723. http://www.expasy.org/spdbv/.
42. http://www.chemaxon.com/.
43. Triballeau N., Acher F., Brabet I., Pin J.P., and Bertrand H.O. J. Med. Chem. 48 (2005) 2534-2547
44. Jmol: an open-source Java viewer for chemical structures in 3D. http://www.jmol.org/.