Identification of novel antitubulin agents by using a virtual screening approach based on a 7-point pharmacophore model of the tubulin colchi-site

Chemical Biology and Drug Design

Volumn 78, Issue 6, 2011, Pages 913-922

  Massarotti, Alberto ^a   Theeramunkong, Sewan ^a   Mesenzani, Ornella ^a   Caldarelli, Antonio ^a   Genazzani, Armando A ^a   Tron, Gian Cesare ^a  

^a UNIVERSITY OF EASTERN PIEDMONT   (Italy)

Author keywords

Colchicine; Drug discovery; Pharmacophore modeling; Tubulin; Virtual screening

Indexed keywords

2 METHOXYESTRADIOL; ANTINEOPLASTIC AGENT; COLCHICINE; COMBRETASTATIN; CURACINE A; INDANOCINE; N [2 [(4 HYDROXYPHENYL)AMINO] 3 PYRIDINYL] 4 METHOXYBENZENESULFONAMIDE; NOCODAZOLE; PODOPHYLLOTOXIN; PROTEIN INHIBITOR; STEGANACIN; TUBULIN INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; DRUG MECHANISM; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FLOW CYTOMETRY; HELA CELL; HUMAN; HUMAN CELL; IMMUNOFLUORESCENCE TEST; IN VITRO STUDY; PHARMACOPHORE; PRIORITY JOURNAL;

BINDING SITES; CELL LINE, TUMOR; COLCHICINE; DATABASES, FACTUAL; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; LIGANDS; MODELS, MOLECULAR; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN; TUBULIN MODULATORS;

EID: 81355124033     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2011.01245.x     Document Type: Article

References (26)

1. Kavallaris M., Verrills N.M., Hill B.T. (2001) Anticancer therapy with novel tubulin-interacting drugs. Drug Resist Updat;4:392-401.
2. Jordan M.A. (2002) Mechanism of action of antitumor drugs that interact with microtubules and tubulin. Curr Med Chem Anticancer Agents;2:1-17.
3. Fojo T. (2008) The Role of Microtubules in Cell Biology, Neurobiology, and Oncology. Totowa: Humana Press.
4. van Loo G., Saelens X., van Gurp M., MacFarlane M., Martin S.J., Vandenabeele P. (2002) The role of mitochondrial factors in apoptosis: a Russian roulette with more than one bullet. Cell Death Differ;9:1031-1042.
5. Luduena R.F., Shooter E.M., Wilson L. (1977) Structure of the tubulin dimer. J Biol Chem;252:7006-7014.
6. Rowinsky E.K., Donehower R.C. (1995) Paclitaxel (taxol). N Engl J Med;332:1004-1014.
7. Kruczynski A., Hill B.T. (2001) Vinflunine, the latest Vinca alkaloid in clinical development. A review of its preclinical anticancer properties. Crit Rev Oncol Hematol;40:159-173.
8. Dumontet C., Jordan M.A. (2010) Microtubule-binding agents: a dynamic field of cancer therapeutics. Nat Rev Drug Discov;9:790-803.
9. Ravelli R.B., Gigant B., Curmi P.A., Jourdain I., Lachkar S., Sobel A., Knossow M. (2004) Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain. Nature;428:198-202.
10. Dorleans A., Gigant B., Ravelli R.B., Mailliet P., Mikol V., Knossow M. (2009) Variations in the colchicine-binding domain provide insight into the structural switch of tubulin. Proc Natl Acad Sci U S A;106:13775-13779.
11. Nguyen T.L., McGrath C., Hermone A.R., Burnett J.C., Zaharevitz D.W., Day B.W., Wipf P., Hamel E., Gussio R. (2005) A common pharmacophore for a diverse set of colchicine site inhibitors using a structure-based approach. J Med Chem;48:6107-6116.
12. Zefirova O.N., Diikov A.G., Zyk N.V., Zefirov N.S. (2007) Ligands of the colchicine site of tubulin: a common pharmacophore and new structural classes. Russ Chem Bull;56:680-688.
13. Ferguson D.M., Raber D.J. (1989) A new approach to probing conformational space with molecular mechanics: random incremental pulse search. J Am Chem Soc;111:4371-4378.
14. Pettit G.R., Singh S.B., Hamel E., Lin C.M., Alberts D.S., Garcia-Kendall D. (1989) Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4. Experientia;45:209-211.
15. Sackett D.L. (1993) Podophyllotoxin, steganacin and combretastatin: natural products that bind at the colchicine site of tubulin. Pharmacol Ther;59:163-228.
16. Lakhani N.J., Sarkar M.A., Venitz J., Figg W.D. (2003) 2-Methoxyestradiol, a promising anticancer agent. Pharmacotherapy;23:165-172.
17. De Brabander M.J., Van de Veire R.M., Aerts F.E., Borgers M., Janssen P.A. (1976) The effects of methyl (5-(2-thienylcarbonyl)-1H-benzimidazol-2-yl) carbamate, (R 17934; NSC 238159), a new synthetic antitumoral drug interfering with microtubules, on mammalian cells cultured in vitro. Cancer Res;36:905-916.
18. Jordan M.A., Thrower D., Wilson L. (1992) Effects of vinblastine, podophyllotoxin and nocodazole on mitotic spindles. Implications for the role of microtubule dynamics in mitosis. J Cell Sci;102(Pt 3):401-416.
19. Hamel E., Lin C.M. (1984) Separation of active tubulin and microtubule-associated proteins by ultracentrifugation and isolation of a component causing the formation of microtubule bundles. Biochemistry;23:4173-4184.
20. Lawrence N.J., McGown A.T. (2005) The chemistry and biology of antimitotic chalcones and related enone systems. Curr Pharm Des;11:1679-1693.
21. Imperio D., Pirali T., Galli U., Pagliai F., Cafici L., Canonico P.L., Sorba G., Genazzani A.A., Tron G.C. (2007) Replacement of the lactone moiety on podophyllotoxin and steganacin analogues with a 1, 5-disubstituted 1, 2, 3-triazole via ruthenium-catalyzed click chemistry. Bioorg Med Chem;15:6748-6757.
22. Davis R.B., Pzzini L.C. (1960) Condensation of aromatic nitro compounds with acrylacetonitriles. II. Some p-substituted nitrobenzenes. J Org Chem;25:1884-1888.
23. Dyall L.K., Karpa G.J. (1988) Pyrolysis of aryl azides. VIII Hammett correlations of rates od pyrolysis of substituted 2-azidobenzophenones. Aust J Chem;41:1231-1241.
24. Inamoto K., Katsumo M., Yoshino T., Arai Y., Hiroya K., Sakamoto T. (2007) Synthesis of 3-substituted indazoles and benzoisoxazoles via Pd-catalyzed cyclization reactions: application to the synthesis of nigellicine. Tetrahedron;63:2695-2711.
25. De P., Nonappa, Pandurangan K., Maitra U., Wailes S. (2007) CuI-mediated cross-coupling of aryl halides with oximes: a direct access to O-aryloximes. Org Lett;9:2767-2770.
26. Pettit G.R., Toki B., Herald D.L., Verdier-Pinard P., Boyd M.R., Hamel E., Pettit R.K. (1998) Antineoplastic agents. 379. Synthesis of phenstatin phosphate. J Med Chem;41:1688-1695.