Structure-activity studies on arylamides and arysulfonamides ras inhibitors

Current Cancer Drug Targets

Volumn 10, Issue 2, 2010, Pages 192-199

  Colombo, S ^a   Palmioli, A ^a   Airoldi, C ^a   Tisi, R ^a   Fantinato, S ^a   Olivieri, S ^a   De Gioia, L ^a   Martegani, E ^a   Peri, F ^a  

^a UNIVERSITY OF MILANO BICOCCA   (Italy)

Author keywords

Anticancer agents; Computational chemistry; Ras; Structure activity relationship

Indexed keywords

AROMATIC AMIDE; HYDROXYLAMINE; RAS PROTEIN; SULFONAMIDE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; EXCISION REPAIR; GENE ACTIVATION; IN VITRO STUDY; MOLECULAR MODEL; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION; VALIDATION STUDY;

ANIMALS; CELL PROLIFERATION; CELL TRANSFORMATION, NEOPLASTIC; CYCLIN-DEPENDENT KINASE INHIBITOR P21; DRUG DESIGN; GUANOSINE DIPHOSPHATE; GUANOSINE TRIPHOSPHATE; HUMANS; HYDROXYLAMINES; INHIBITORY CONCENTRATION 50; MICE; MOLECULAR STRUCTURE; MUTATION; NIH 3T3 CELLS; RAS PROTEINS; RAS-GRF1; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; TWO-HYBRID SYSTEM TECHNIQUES;

EID: 77950664561     PISSN: 15680096     EISSN: None     Source Type: Journal    
DOI: 10.2174/156800910791054185     Document Type: Article

References (25)

1. Barbacid, M. ras Genes. Annu. Rev. Biochem. 1987, 56, 779-827.
2. Lowy, D. R.; Willumsen, B. M. Function and regulation of Ras. Annu. Rev. Biochem. 1993, 62, 851-891.
3. Voijtec, A. B.; Der, C. J. Increasing Complexity of the Ras Signaling Pathway. J. Biol. Chem. 1998, 273, 19925-19928.
4. Diaz-Flores, E.; Shannon, K. Targeting oncogenic Ras. Genes Dev 2007, 21, 1989-1992.
5. Wittinghofer, H.; Waldmann, H. Ras: a molecular switch involved in tumor formation. Angew. Chem. Int. Ed. 2000, 39, 4192-4214.
6. Midgley, R. S.; Kerr, D. J. Ras as a target in cancer therapy. Crit. Rev. Oncol./Hematol. 2002, 44, 109-120.
7. Friday, B. B.; Adjei, A. A. K-ras as a target for cancer therapy. Biochim. Biophys. Acta Rev. Cancer 2005, 1756, 127-144.
8. Ellis, C. A.; Clark, G. The importance of being K-Ras. Cell. Signal. 2000, 12, 425-434.
9. Taveras, A. G.; Remiszewsky, S. W.; Doll, R. J.; Cesarz, D.; Huang, E. C.; Kirschmeier, P.; Pramanik, B. N.; Snow, M. E.; Wang, Y .-S.; del Rosario, J. D.; Vibulbhan, B.; Bauer, B. B.; Brown, J. E.; Carr, D.; Catino, J.; Evans, C. A.; Girijavallabhan, V.; Heimark, L.; James, L.; Liberles, S.; Nash, C.; Perkins, L.; Senior, M. M.; Tsarbopoulos, A.; Ganguly, A. K.; Aust, R.; Brown, E.; Delisle, D.; Fuhrman, S.; Hendrickson, T.; Kissinger, C.; Love, R.; Sisson, W.; Villafranca, E.; Webber, S. E. Ras oncoprotein inhibitors: the discovery of potent, ras nucleotide exchange inhibitors and the structural determination of drug-protein complex. Biooorg. Med. Chem. 1997, 5, 125-133.
10. Ganguly, A. K.; Wang, Y. -S.; Pramanik, B. N.; Doll, R. J.; Snow, M. E.; Taveras, A. G.; Remiszewski, S.; Cesarz, D.; del Rosario, J.; Vibulbhan, B.; Brown, J. E.; Kirschmeier, P.; Huang, E. C.; Heimark, L.; Tsarbopoulos, A.; Girijavallabhan, V. M. Detection and structural characterization of Ras oncoprotein-inhibitors complexes by electrospray mass spectrometry. Biochemistry 1998, 37, 15631-15637.
11. Colombo, S.; Peri, F.; Tisi, R.; Nicotra, F.; Martegani, E. Design and characterization of a new class of inhibitors of Ras activation. Ann. NY Acad. Sci. 2004, 1030, 52-61.
12. Peri, F.; Airoldi, C.; Colombo, S.; Martegani, E.; van Neuren, A. S.; Stein, M.; Marinzi, C.; Nicotra, F. Design, synthesis, and biological evaluation of sugar-derived Ras inhibitors. ChemBioChem. 2005, 6, 1839-1848.
13. Peri, F.; Airoldi, C.; Colombo, S.; Mari, S.; Jiménez-Barbero, J.; Martegani, E.; Nicotra, F. Sugar-derived Ras inhibitors: group epitope mapping by NMR spectroscopy and biological evaluation. Eur. J. Org. Chem. 2006, 16, 3707-3720.
14. Airoldi, C.; Palmioli, A.; D'Urzo, A.; Colombo, S.; Vanoni, M.; Martegani, E.; Peri, F. Glucose-derived Ras pathway inhibitors: evidence of Ras-ligand binding and Ras-GEF (Cdc25) interaction inhibition. ChemBioChem 2007, 8, 1376-1379.
15. Mosteller, R. D.; Park, W.; Broek, D. Analysis of interaction between Ras and CDC25 guanine nucleotide exchange factor using yeast GAL4 two-hybrid system. Methods Enzymol. 1995, 255, 135-148.
16. Lenzen, C.; Cool, R. H.; Wittinghofer, A. Analysis of intrinsic and CDC25-stimulated guanine nucleotide exchange of p21rasnucleotide complexes by fluorescence measurements. Methods Enzymol. 1995, 255, 95-109.
17. N-ras. J. Biol. Chem. 1986, 261, 10963-10965.
18. Milburn, M. V.; Tong, L.; de Vos, A. M.; Brunger, A.; Yamaizumi, Z.; Nishimura, S.; Kim, S. H. Molecular switch for signal transduction: structural differences between active and inactive forms of protooncogenic ras proteins. Science 1990, 247, 939-945.
19. Shoichet, B. Virtual screening of chemical libraries. Nature 2004, 432, 862-865.
20. Martegani, E.; Vanoni, M.; Zippel, R.; Coccetti, P.; Brambilla, R.; Ferrari, C.; Sturani, F.; Alberghina, L. Cloning by functional complementation of a mouse cDNA encoding a homologue of CDC25, a Saccharomyces cerevisiae RAS activator. EMBO J. 1992, 11, 2151-2157.
21. Coccetti, P.; Mauri, L.; Alberghina, L.; Martegani, E.; Parmeggiani, A. The Minimal Active Domain of the Mouse Ras Exchange Factor CDC25Mm. Biochem. Biophys. Res. Commun. 1995, 206, 253-259.
22. Kiechle, M.; Manivasakam, P.; Eckardt-Schupp, F.; Schiestl, R. H.; Friedl, A. Promoter-trapping in Saccharomyces cerevisiae by radiation-assisted fragment insertion. Nucleic Acids Res. 2002, 30, 136-143.
23. Halgren, T. A. Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94. J. Comput. Chem. 1996, 17, 490-519.
24. Gasteiger, H. J.; Marsili, M. A New Model for Calculating Atomic Charges in Molecules. Tetrahedron Lett. 1978, 34, 3181-3184.
25. Wallace, A. C.; Laskowski, R. A.; Thornton, J. M. LIGPLOT: A program to generate schematic diagrams of protein-ligand interactions. Prot. Eng. 1995, 8, 127-134.