Synthesis, molecular modeling and biological evaluation of dithiocarbamates as novel antitubulin agents

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 12, 2010, Pages 4310-4316

  Qian, Yong ^a   Ma, Gao Yuan ^a   Yang, Ying ^a   Cheng, Kui ^a   Zheng, Qing Zhong ^a   Mao, Wen Jun ^a   Shi, Lei ^a   Zhao, Jing ^a   Zhu, Hai Liang ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

Antitubulin polymerization; Chalcone; Dithiocarbmate; Molecular modeling

Indexed keywords

1 (2 CHLOROPHENYL) 3 (4 METHOXYPHENYL) 3 OXOPROPYL DIETHYLCARBAMODITHIOATE; 1 (2 CHLOROPHENYL) 3 OXO 3 PHENYLPROPYL DIETHYLCARBAMODITHIOATE; 1 (2 METHOXYPHENYL) 3 OXO 3 PHENYLPROPYL DIETHYLCARBAMODITHIOATE; 1 (3 NITROPHENYL) 3 OXO 3 PHENYLPROPYL DIETHYLCARBAMODITHIOATE; 1 (4 BROMOPHENYL) 3 OXO 3 PHENYLPROPYL DIETHYLCARBAMODITHIOATE; 1 (4 CHLOROPHENYL) 3 (4 METHOXYPHENYL) 3 OXOPROPYL DIETHYLCARBAMODITHIOATE; 1 (4 CHLOROPHENYL) 3 OXO 3 PHENYLPROPYL DIETHYLCARBAMODITHIOATE; 1 (4 FLUOROPHENYL) 3 OXO 3 PHENYLPROPYL DIETHYLCARBAMODITHIOATE; 1 (4 METHOXYPHENYL) 3 OXO 3 PHENYLPROPYL DIETHYL CARBAMODITHIOATE; 1,3 BIS (4 METHOXYPHENYL) 3 OXOPROPYL DIETHYLCARBAMODITHIOATE; 3 (3,4 DICHLOROPHENYL) 3 OXO 1 PHENYLPROPYL DIETHYLCARBAMODITHIOATE; 3 (4 BROMOPHENYL) 1 (4 FLUOROPHENYL) 3 OXOPROPYL DIETHYLCARBAMODITHIOATE; 3 (4 BROMOPHENYL) 1 (4 METHOXYPHENYL) 3 OXOPROPYL DIETHYLCARBAMODITHIOATE; 3 (4 BROMOPHENYL) 3 OXO 1 PHENYLPROPYL DIETHYLCARBAMODITHIOATE; 3 (4 CHLOROPHENYL) 3 OXO 1 PHENYLPROPYL DIETHYLCARBAMODITHIOATE; 3 (4 METHOXYPHENYL) 3 OXO 1 P TOLYLPROPYL DIETHYLCARBAMODITHIOATE; 3 (4 METHOXYPHENYL) 3 OXO 1 PHENYLPROPYL DIETHYLCARBAMODITHIOATE; 3 OXO 1 PHENYLBUTYL DIETHYLCARBAMODITHIOATE; 3 OXO 1,3 DIPHENYLPROPYL DIETHYLCARBAMODITHIOATE; 3 OXO 3 PHENYL 1 P TOLYLPROPYL DIETHYLCARBAMODITHIOATE; ANTINEOPLASTIC AGENT; COLCHICINE; COMBRETASTATIN A4; DITHIOCARBAMIC ACID DERIVATIVE; TUBULIN; TUBULIN MODULATOR; UNCLASSIFIED DRUG; 3-(4-CHLOROPHENYL)-3-OXO-1-PHENYLPROPYL DIETHYLCARBAMODITHIOATE; CHALCONE; N,N' ETHYLENEBIS(DITHIOCARBAMIC ACID) DERIVATIVE; THIOCARBAMIC ACID DERIVATIVE;

ARTICLE; CANCER CELL CULTURE; CANCER GROWTH; CANCER INHIBITION; CELL STRAIN MCF 7; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG BINDING SITE; DRUG MECHANISM; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; MICROTUBULE ASSEMBLY; MOLECULAR MODEL; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; CONFORMATION; ENZYME ACTIVE SITE; METABOLISM; SYNTHESIS; TUMOR CELL LINE; X RAY CRYSTALLOGRAPHY;

BINDING SITES; CATALYTIC DOMAIN; CELL LINE, TUMOR; CHALCONE; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; ETHYLENEBIS(DITHIOCARBAMATES); HUMANS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; THIOCARBAMATES; TUBULIN; TUBULIN MODULATORS;

RUMEX;

EID: 77953140221     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.04.091     Document Type: Article

References (35)

1. Valiron O., Caudron N., and Job D. Cell. Mol. Life Sci. 58 (2001) 2069
2. Hamel E. Med. Chem. Rev. 16 (1996) 207
3. Kim D.Y., Kim K.H., Kim N.D., Lee K.Y., Han C.K., Yoon J.H., Moon S.K., Lee S.S., and Seong B.L. J. Med. Chem. 49 (2006) 5664
4. Chinigo G.M., Paige M., Grindrod S., Hamel E., Dakshamamurthy S., Chruszcz M., Minor W., and Brown M.L. J. Med. Chem. 51 (2008) 4620
5. Romagnoli R., Baraldi P.G., Carrion M.D., Cruz-Lopez O., Cara C.L., Basso G., Viola G., Khedr M., Balzarini J., Mahboobi S., Sellmer A., Brancale A., and Hamel E. J. Med. Chem. 52 (2009) 5551
6. Pettit G.R., Singh S.B., Hamel E., Lin C.M., Alberts D.S., and Garcia-Kendall D. Experentia 45 (1989) 209
7. Lin C.M., Ho H.H., Pettit G.R., and Hamel E. Biochemistry 28 (1989) 6984
8. Ravelli R.B., Gigant B., Curmi P.A., Jourdain I., Lachkar S., Sobel A., and Knossow M. Nature 428 (2004) 198
9. Lawrence N.J., and McGown A.T. Curr. Pharm. Des. 11 (2005) 1679
10. Nowakowska Z. Eur. J. Med. Chem. 42 (2007) 125
11. Boumendjel A., Boccard J., Carrupt P.-A., Nicolle E., Blanc M., Geze A., Choisnard L., Wouessidjewe D., Matera E.-L., and Dumontet C. J. Med. Chem. 51 (2008) 2307
12. Cabrera M., Simoens M., Falchi G., Lavaggi M.L., Piro O.E., Castellano E.E., Vidal A., Azqueta A., Monge A., Lopez de Cerain A., Sagrera G., Seoane G., Cerecetto H., and Gonzalez M. Bioorg. Med. Chem. 15 (2007) 3356
13. Sabzevari O., Galati G., Moridani M.Y., Siraki A., and O'Brien P.J. Chem. Biol. Interact. 148 (2004) 57
14. Rao Y.K., Fang S.-H., and Tzeng Y.-M. Bioorg. Med. Chem. 12 (2004) 2679
15. Liu M., Wilairat P., Croft S.L., Tan A.L.-C., and Go M.-L. Bioorg. Med. Chem. 11 (2003) 2729
16. Lunardi F., Guzela M., Rodriguez A.T., Correa R., Eger-Mangrich I., Steindel M., Grisard E.C., Assreuy J., Calixto J.B., and Santos A.R.S. Antimicrob. Agents Chemother. 47 (2003) 1449
17. Go M.L., Wu X., and Liu X.L. Curr. Med. Chem. 12 (2005) 483
18. Kerr D.J., Hamel E., Jung M.K., and Flynn B.L. Bioorg. Med. Chem. 15 (2007) 3290
19. Jung J.C., Jang S., Lee Y., Min D., Lim E., Jung H., Miyeon Oh., Seikwan Oh., and Jung M. J. Med. Chem. 51 (2008) 4054
20. Cvek B., and Dvorak Z.T. Curr. Pharm. Des. 30 (2007) 3155
21. Safak C., Erdogan H., Ertan M., and Yulug N. J. Chem. Soc. Rak. 12 (1990) 296
22. Aragonés J., López-Rodrĺguez C., Corbi A., Gómez del Arco P., López-Cabrera M., Landazuri M., and Redondo J.M. J. Biol. Chem. 271 (1996) 10924
23. Xie J., Funakoshi T., Shimada H., and Kojima S. J. Appl. Toxicol. 16 (1997) 317
24. Funakoshi T., Ueda K., Shimada H., and Kojima S. Toxicology 116 (1997) 99
25. Tandon S.K., Singh S., and Prasad S. Hum. Exp. Toxicol. 16 (1997) 557
26. Huang W., Ding Y., Miao Y., Liu M.Z., Li Y., and Yang G.F. Eur. J. Med. Chem. 44 (2009) 3687
27. Azizi N., Ebrahimi F., Aakbari E., Aryanasab F.R., and Saidi M. Synlett (2007) 2797
28. Huey R., Morris G.M., Olson A.J., and Goodsell D.S. J. Comput. Chem. 28 (2007) 1145
29. De Martino G., Edler M.C., La Regina G., Coluccia A., Barbera M.C., Barrow D., Nicholson R.I., Chiosis G., Brancale A., Hamel E., Artico M., and Silvestri R. J. Med. Chem. 49 (2006) 947
30. Zhang Q., Peng Y.Y., Wang X.I., Keenan S.M., Arora S., and Welsh W.J. J. Med. Chem. 50 (2007) 749
31. Chiang Y.K., Kuo C.C., Wu Y.S., Chen C.T., Coumar M.S., Wu J.S., Hsieh H.P., Chang C.Y., Jseng H.Y., Wu M.H., Leou J.S., Song J.S., Chang J.Y., Lyu P.C., Chao Y.S., and Wu S.Y. J. Med. Chem. 52 (2009) 4221
32. Sheldrick, G. M. shelx-97. Program for X-ray Crystal Structure Solution and Refinement, Göttingen University, Germany, 1997.
33. Hamel E., and Lin C.M. Biochemistry 23 (1984) 4173
34. Hamel E. Cell Biochem. Biophys. 38 (2003) 1
35. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A.J. J. Comput. Chem. 19 (1998) 1639