Synthesis and biological evaluation of novel thiocolchicine-podophyllotoxin conjugates

European Journal of Medicinal Chemistry

Volumn 45, Issue 1, 2010, Pages 219-226

  Passarella, Daniele ^a   Peretto, Bruno ^a   Blasco y Yepes, Raul ^b   Cappelletti, Graziella ^a   Cartelli, Daniele ^a   Ronchi, Cristina ^a   Snaith, John ^c   Fontana, Gabriele ^d   Danieli, Bruno ^a   Borlak, Jurgen ^e  

^a UNIVERSITY OF MILAN   (Italy)

^b CENTRO DE INVESTIGACIÓN PRÍNCIPE FELIPE   (Spain)

^c UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^d INDENA S P A   (Italy)

^e HANNOVER MEDICAL SCHOOL   (Germany)

Author keywords

Anticancer drugs; Microtubule network; Podophyllotoxin; Thiocolchicine; Tubulin polymerization

Indexed keywords

2 AMINOPROPANAMIDE 3,3' DITHIOBIS[N(N DEACETYLTHIOCOLCHICINYL)]; 2,7 DIAMINOOCTANEDIAMIDE N(N DEACETYLTHIOCOLCHICINYL); ACETAMIDE 2,2' DITHIOBIS[N(N DEACETYLTHIOCOLCHICINYL)]; COLCHICINE DERIVATIVE; DIADIPAMIDE N(N DEACETYLTHIOCOLCHICINYL); DIPODOPHYLLOTOXIN 4 YL 2,2' DITHIOBISACETATE; DIPODOPHYLLOTOXIN 4 YL 3,3' BISTHIO 2 AMINO PROPANOATE; DIPODOPHYLLOTOXIN 4 YL ADIPATE; GLUTATHIONE; PODOPHYLLOTOX 4 YL 4 [N(N DEACETYLTHIOCOLCHICINYL) 4 OXOBUTYL DISULFANYL BUTANOATE; PODOPHYLLOTOXIN DERIVATIVE; PROPANAMIDE 3,3' DITHIOBIS[N(N DEACETYLTHIOCOLCHICINYL)]; THIOCOLCHICINE; TUBULIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IMMUNOFLUORESCENCE; MICROTUBULE ASSEMBLY; MOUSE; NONHUMAN; POLYMERIZATION;

ANIMALS; CATTLE; CELL LINE, TUMOR; COLCHICINE; FLUORESCENT ANTIBODY TECHNIQUE; GLUTATHIONE; HUMANS; INHIBITORY CONCENTRATION 50; MICE; PODOPHYLLOTOXIN; PROTEIN MULTIMERIZATION; PROTEIN STRUCTURE, QUATERNARY; TUBULIN;

EID: 72049120386     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.09.047     Document Type: Article

References (39)

1. Thorpe P.E., Chaplin D.J., and Blakey D.C. The first international conference on vascular targeting: meeting overview. Cancer Res. 63 (2003) 1144-1147
2. Jordan M., and Curr A. Med. Chem. Anticancer Agents 2 (2002) 1-17
3. For the mechanism of action of binary vinca alkaloids see:
4. Rai S.S., and Wolff J.J. Biol. Chem. 271 (1996) 14707-14711
5. Gigant B., Wang C., Ravelli R.B.G., Roussi F., Steinmetz M.O., Curmi P.A., Sobel A., and Knowssow M. Nature 435 (2005) 519-522
6. For the mechanism of action of taxanes and Paclitaxel see:
7. Wilson L., Miller H.P., Farrell K.W., Snyder K.B., Thompson W.C., and Purich D.L. Biochemistry 24 (1985) 5254-5262
8. Schiff P.B., and Horwitz S.B. Proc. Natl. Acad. Sci. USA 77 (1980) 1561-1565
9. Schiff P.B., Fant J., and Horwitz S.B. Nature 277 (1979) 665-667
10. Snyder J.P., Nettles J.H., Cornett B., Downing K.H., and Nogales E. Proc. Natl. Acad. Sci. USA 98 (2001) 5312-5316
11. Bai R., Covell D.G., Pei X.-F., Ewelli J.B., Nguyeni N.Y., Brossi A., and Hamel E.J. Biol. Chem. 275 (2000) 40443-40452
12. Cowan C.R., and Cande W.Z. J. Cell Sci. 115 (2002) 3747-3756
13. Tseng C.J., Wang Y.J., Liang Y.C., Jeng J.H., Lee W.S., Lin J.K., Chen C.H., Liu I.C., and Ho Y.S. Toxicology 175 (2002) 123-142
14. Uppuluri S., Knipling L., Sackett D.L., and Wolff J. Proc. Natl. Acad. Sci. U.S.A 90 (1993) 11598-11602
15. In: Brossi A. (Ed). The alkaloids vol. 23 (1984), Academic Press, New York
16. Sackett D.L., and Varma J.K. Biochemistry 32 (1993) 13560-13565
17. Jain R.K. Science 307 (2005) 58-62
18. For recent examples of synthesis of tubulin polymerization inhibitors see:
19. Keller L., Beaumont S., Liu J.-M., Thoret S., Bignon J.S., Wdzieczak-Bakala J., Dauban P., and Dodd R.H. J. Med. Chem. 51 (2008) 3414-3421
20. Zhang Q., Peng Y., Wang X.I., Keenan S.M., Arora S., and Welsh W.J. J. Med. Chem. 50 (2007) 749-754
21. Zuse A., Schmidt P., Baasner S., Böhm K.J., Müller K., Gerlach M., Günther E.G., Unger E., and Prinz H. J. Med. Chem. 49 (2006) 7816-7825
22. Attard G., Greystoke A., Kaye S., and De Bono J. Pathol. Biol. 54 (2006) 72-84
23. Langer M., Kratz F., Rothen-Rutishauser B., Wunderli-Alemnspach H., and Beck-Sickinger A.G. J. Med. Chem. 44 (2001) 1341-1348
24. Safavy A., Bonner J.A., Waksal H.W., Buchsbaum D.J., Gillespie G.Y., Khazaeli M.B., Arani R., Chen D.T., Carpenter M., and Raisch K.P. Bioconjug. Chem. 14 (2003) 302-310
25. Corson T.W., Aberle N., and Crews C.M. ACS Chem. Biol. 3 (2008) 677-692
26. Mammen M., Choi S.-K., and Whitesides G.M. Angew. Chem. Int. Ed. 37 (1998) 2754-2794
27. See as examples:
28. Camps P., Formosa X., Munoz-Torrero D., Petrignet J., Badia A., and Clos M.V. J. Med. Chem. 48 (2005) 1701-1704
29. Feng S., Wang Z., He X., Zheng S., Xia Y., Jiang H., Tang X., and Bai D. J. Med. Chem. 48 (2005) 655-657
30. Bombuwala K., Kinstle T., Popik V., Uppal S.O., Olesen J.B., Vina J., and Heckman C.A. Beilstein J. Org. Chem. 2 (2006) 13
31. Chen S.-W., Xiang R., Liu J., and Tian X. Bioorg. Med. Chem. 17 (2009) 3111-3117
32. Danieli B., Lesma G., Martinelli M., Passarella D., Silvani A., Pyuskyulev B., and Tam M.N. J. Org. Chem. 63 (1998) 8586-8588
33. Danieli B., Giardini A., Lesma G., Passarella D., Silvani A., Appendino G., Noncovich A., Fontana G., Bombardalli E., and Sterner O. Chem. Biodivers. 1 (2004) 327-345
34. Passarella D., Giardini A., Peretto B., Fontana G., Sacchetti A., Silvani A., Cappelletti G., Ronchi D., Cartelli C., Borlak J., and Danieli B. Bioorg. Med. Chem. 16 (2008) 6269-6285
35. Danieli B., Giardini A., Lesma G., Passarella D., Peretto B., Sacchetti S., Silvani A., and Pratesi G. J. Org. Chem. 71 (2006) 2848-2853
36. 3: C, 58.42; H, 5.83; N, 3.52. Found: C, 58.44; H, 5.82; N, 3.53
37. Reamon-Buettner S.M., and Borlak J. Cancer Res. 68 (2008) 7587-7596
38. Hamel E. Cell Biochem. Biophys. 38 (2003) 1-21
39. Cappelletti G., Maggioni M.G., and Maci R. J. Neurosci. Res. 56 (1999) 28-35