Docking, 3D-QSAR studies and in silico ADME prediction on c-Src tyrosine kinase inhibitors

European Journal of Medicinal Chemistry

Volumn 44, Issue 3, 2009, Pages 990-1000

  Tintori, Cristina ^a   Magnani, Matteo ^a   Schenone, Silvia ^b   Botta, Maurizio ^a  

^a UNIVERSITY OF SIENA   (Italy)

^b UNIVERSITY OF GENOA   (Italy)

Author keywords

3D QSAR; ADME; c Src; Docking

Indexed keywords

PROTEIN TYROSINE KINASE INHIBITOR;

ARTICLE; DRUG PENETRATION; DRUG SOLUBILITY; DRUG STRUCTURE; HUMAN; HYDROGEN BOND; HYDROPHOBICITY; ONCOGENE SRC; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

BINDING SITES; MODELS, MOLECULAR; PROTEIN KINASE INHIBITORS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SRC-FAMILY KINASES; STATIC ELECTRICITY;

EID: 60549100326     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.07.002     Document Type: Article

References (42)

1. Ullrich A., and Schlessinger J. Cell 61 (1990) 203-212
2. Johnson L.N., Noble M.E., and Owen D.J. Cell 85 (1996) 149-158
3. Neet K., and Hunter T. Genes Cells 1 (1996) 147-169
4. Aligayer H., Boyd D.D., Heiss M.M., Abdalla E.K., Curley S.A., and Gallick G.E. Cancer 94 (2002) 344-351
5. Belsches-Jablonski A.P., Biscardi J.S., Peavy D.R., Tice D.A., Romney D.A., and Parsons S.J. Oncogene 20 (2001) 1465-1475
6. MacMillan-Crow L.A., Greendorfer J.S., Vickers S.M., and Thompson J.A. Arch. Biochem. Biophys. 377 (2000) 350-356
7. Boyce B.F., Yoneda T., Lowe C., Soriano P., and Mundy G.R. J. Clin. Invest. 90 (1992) 1622-1627
8. Umemori H., Sato S., Yagi T., Aizawa S., and Yamamoto T. Nature 367 (1994) 572-576
9. Weis S., Shintani S., Weber A., Kirchmair R., Wood M., Cravens A., McSharry H., Iwakura A., Yoon Y.S., Himes N., Burstein D., Doukas J., Soll R., Losordo D., and Cheresh D. J. Clin. Invest. 113 (2004) 885-894
10. Paul R., Zhang Z.G., Eliceiri B.P., Jiang Q., Boccia A.D., Zhang R.L., Chopp M., and Cheresh D.A. Nat. Med. 7 (2001) 222-227
11. Nixon R.R. J. Biol. Chem. 280 (2005) 2455-2462
12. Schenone S., Manetti F., and Botta M. Curr. Pharm. Des. 13 (2007) 2118-2128
13. Donnini S., Monti M., Castagnini C., Solito R., Botta M., Schenone S., Giochetti A., and Ziche M. Int. J. Cancer 120 (2007) 995-1004
14. Dow R.L., Bechle B.M., Chou T.T., Goddard C., and Larson E.R. Bioorg. Med. Chem. Lett. 5 (1995) 1007-1010
15. Myers M.R., Setzer N.N., Spada A.P., Zulli A.L., Hsu C.-Y.J., Zilberstein A., Johnson S.E., Hook L.E., and Jacoski M.V. Bioorg. Med. Chem. Lett. 7 (1997) 417-420
16. Hanke J.H., Gardner J.P., Dow R.L., Changelian P.S., Brissette W.H., Weringer E.J., Pollok B.A., and Connelly P.A. J. Biol. Chem. 271 (1996) 695-701
17. Carraro F., Naldini A., Pucci A., Locatelli G.A., Maga G., Schenone S., Bruno O., Ranise A., Bondavalli F., Brullo C., Fossa P., Menozzi G., Mosti L., Modugno M., Tintori C., Manetti F., and Botta M. J. Med. Chem. 49 (2006) 1549-1561
18. Missbach M., Altmann E., Widler L., Susa M., Buchdunger E., Mett H., Meyer T., and Green J. Bioorg. Med. Chem. Lett. 10 (2000) 945-949
19. Widler L., Green J., Missbach M., Susa M., and Altmann E. Bioorg. Med. Chem. Lett. 11 (2001) 849-852
20. Altmann E., Missbach M., Green J., Susa M., Wagenknecht H.-A., and Widler L. Bioorg. Med. Chem. Lett. 11 (2001) 853-856
21. Altmann E., Widler L., and Missbach M. Mini Rev. Med. Chem. 2 (2002) 201-208
22. Noronha G., Barrett K., Boccia A., Brodhag T., Cao J., Chow C.P., Dneprovskaia E., Doukas J., Fine R., Gong X., Gritzen C., Gu H., Hanna E., Hood J.D., Hu S., Kang X., Key J., Klebansky B., Kousba A., Li G., Lohse D., Mak C.C., McPherson A., Palanki M.S., Pathak V.P., Renick J., Shi F., Soll R., Splittgerber U., Stoughton S., Tang S., Yee S., Zeng B., Zhao N., and Zhu H. Bioorg. Med. Chem. Lett. 17 (2007) 602-608
23. Klutchko S.R., Hamby J.M., Boschelli D.H., Wu Z., Kraker A.J., Amar A.M., Hartl B.G., Shen C., Klohs W.D., Steinkampf R.W., Driscoll D.L., Nelson J.M., Elliott W.L., Roberts B.J., Stoner C.L., Vincent P.W., Dykes D.J., Panek R.L., Lu G.H., Major T.C., Dahring T.K., Hallak H., Bradford L.A., Showalter H.D., and Doherty A.M. J. Med. Chem. 41 (1998) 3276-3292
24. Thompson A.M., Rewcastle G.W., Biushelle S.L., Hartl B.G., Kraker A.J., Lu G.H., Batley B.L., Panek R.L., Showalter H.D.H., and Denny W.A. J. Med. Chem. 43 (2000) 3134-3147
25. Cramer III R.D., Patterson D.E., and Bunce J.D. J. Am. Chem. Soc. 110 (1988) 5939-5967
26. Cruciani G., and Watson K.A. J. Med. Chem. 37 (1994) 2589-2601
27. Ragno R., Simeoni S., Valente S., Massa S., and Mai A. J. Chem. Inf. Model. 46 (2006) 1420-1430
28. Caballero J., Fernández M., Saavedra M., and Gonzáles-Nilo F.D. Bioorg. Med. Chem. 16 (2008) 810-821
29. Oblak M., Randic M., and Solmajer T. J. Chem. Inf. Comput. Sci. 4 (2000) 994-1001
30. Shen Q., Lu Q.-Z., Jiang J.-H., Shen G.-L., and Yu R.-Q. Eur. J. Pharm. Sci. 20 (2003) 63-71
31. Guha R., and Jurs P.C. J. Chem. Inf. Comput. Sci. 44 (2004) 2179-2189
32. Chen G., Luo X., Zhu W., Luo C., Liu H., Phua C.M., Chena K., and Jiang H. Bioorg. Med. Chem. 12 (2004) 2409-2417
33. Thaimattam R., Daga P.R., Banerjee R., and Iqbal J. Bioorg. Med. Chem. 13 (2005) 4704-4712
34. Cruciani G., Pastor M., and Guba W. Eur. J. Pharm. Sci. 11 Suppl. 2 (2000) S29-S39
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) 1639-1662
36. Breitenlechner C.B., Norman A.K., Scheiblich K.H.S., Koll H., Greiter E., Koch S., Schafer W., Huber R., and Engh R.A. J. Mol. Biol. 353 (2005) 222-231
37. Further information at the web site:.
38. GRID 22, Molecular Discovery Ltd, 215 Marsh Road, Pinner, Middlesex, UK.
39. GOLPE 4.5, Multivariate Infometric Analyses Srl, Viale dei Castagni 16, Perugia, Italy, 1999.
40. Wold S., Johansson E., and Cocchi M. In: Kubinyi H. (Ed) (1993), 3D QSAR in Drug Design, Theory, Methods and Applications, Escom, Leiden 523-550
41. Celano M., Schenone S., Cosco D., Navarra M., Puxeddu E., Racanicchi L., Brullo C., Varano E., Alcaro S., Ferretti E., Botta G., Filetti S., Fresta M., Botta M., and Russo D. Endocr. Relat. Cancer, 15 (2008) 499-510
42. Mukaiyama H., Nishimura T., Shiohara H., Kobayashi S., Komatsu Y., Kikuchi S., Tsuji E., Kamada N., Ohnota H., and Kusama H. Chem. Pharm. Bull. 55 (2007) 881-889