Structural studies of B-type Aurora kinase inhibitors using computational methods

Acta Pharmacologica Sinica

Volumn 31, Issue 2, 2010, Pages 244-258

  Neaz, M M ^b,c   Muddassar, M ^b,c   Pasha, F A ^b,d   Cho, Seung Joo ^a  

^a Chosun University   (South Korea)

^b Korea Institute of Science and Technology   (South Korea)

^c University of Science and Technology (UST)   (South Korea)

^d IFP ENERGIES NOUVELLES   (France)

Author keywords

3D QSAR; Aurora B; CoMFA; CoMSIA; Drug design; Kinase

Indexed keywords

AURORA KINASE B INHIBITOR; AURORA KINASE INHIBITOR; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG STRUCTURE; IC 50; MOLECULAR MODEL; PARTIAL LEAST SQUARES REGRESSION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; THREE DIMENSIONAL IMAGING;

LEAST-SQUARES ANALYSIS; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN KINASE INHIBITORS; PROTEIN-SERINE-THREONINE KINASES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 76949083497     PISSN: 16714083     EISSN: 17457254     Source Type: Journal    
DOI: 10.1038/aps.2009.188     Document Type: Article

References (54)

1. Andrews PD. Aurora kinases: shining lights on the therapeutic horizon? Oncogene 2005; 24: 5005-15.
2. Matthews N, Visintin C, Hartzoulakis B, Jarvis A, Selwood DL. Aurora A and B kinases as targets for cancer: will they be selective for tumors? Expert Rev Anticancer Ther 2006; 6: 109-20.
3. Girdler F, Gascoigne KE, Eyers PA, Hartmuth S, Crafter C, Foote KM, et al. Validating Aurora B as an anti-cancer drug target. J Cell Sci 2006; 119: 3664-75.
4. Andrews PD, Knatko E, Moore WJ, Swedlow JR. Mitotic mechanics: the auroras come into view. Curr Opin Cell Biol 2003; 15: 672-83.
5. Carmena M, Earnshaw WC. The cellular geography of aurora kinases. Nat Rev Mol Cell Biol 2003; 4: 842-54.
6. Meraldi P, Honda R, Nigg EA. Aurora kinases link chromosome segregation and cell division to cancer susceptibility. Curr Opin Genet Dev 2004; 14: 29-36.
7. Giet R, Glover DM. Drosophila Aurora B kinase is required for histone H3 phosphorylation and condensin recruitment during chromosome condensation and to organize the central spindle during cytokinesis. J Cell Biol 2001; 152: 669-81.
8. Bischoff JR, Anderson L, Zhu YF, Mossie K, Ng L, Souza B, et al. A homologue of Drosophila aurora kinase is oncogenic and amplified in human colorectal cancers. Embo J 1998; 17: 3052-65.
9. Royce ME, Xia WY, Sahin AA, Katayama H, Johnston DA, Hortobagyi G, et al. STK15/aurora-A expression in primary breast tumors is correlated with nuclear grade but not with prognosis. Cancer 2004; 100: 12-9.
10. Sen S, Zhou HY, White RA. A putative serine/threonine kinase encoding gene BTAK on chromosome 20q13 is amplified and overexpressed in human breast cancer cell lines. Oncogene 1997; 14: 2195-200.
11. Tanaka T, Kimura M, Matsunaga K, Fukada D, Mori H, Okano Y. Centrosomal kinase AIK1 is overexpressed in invasive ductal carcinoma of the breast. Cancer Res 1999; 59: 2041-44.
12. Chieffi P, Cozzolino L, Kisslinger A, Libertini S, Staibano S, Mansueto G, et al. Aurora B expression directly correlates with prostate cancer malignancy and influence prostate cell proliferation. Prostate 2006; 66: 326-33.
13. Li DH, Zhu JJ, Firozi PF, Abbruzzese JL, Evans DB, Cleary K, et al. Overexpression of oncogenic STK15/BTAK/aurora A kinase in human pancreatic cancer. Clin Cancer Res 2003; 9: 991-7.
14. Ulisse S, Delcros JG, Baldini E, Toller M, Curcio F, Giacomelli L, et al. Expression of Aurora kinases in human thyroid carcinoma cell lines and tissues. Int J Cancer 2006; 119: 275-82.
15. Reiter R, Gais P, Jutting U, Steuer-Vogt MK, Pickhard A, Bink K, et al. Aurora kinase A messenger RNA overexpression is correlated with tumor progression and shortened survival in head and neck squamous cell carcinoma. Clin Cancer Res 2006; 12: 5136-41.
16. Ikezoe T, Yang J, Nishioka C, Tasaka T, Taniguchi A, Kuwayama Y, et al. A novel treatment strategy targeting Aurora kinases in acute myelogenous leukemia. Mol Cancer Ther 2007; 6: 1851-7.
17. Zeng WF, Navaratne K, Prayson RA, Weil RJ. Aurora B expression correlates with aggressive behaviour in glioblastoma multiforme. J Clin Pathol 2007; 60: 218-21.
18. Lopez-Rios F, Chuai S, Flores R, Shimizu S, Ohno T, Wakahara K, et al. Global gene expression profiling of pleural mesotheliomas: Overexpression of aurora kinases and P16/CDKN2A deletion as prognostic factors and critical evaluation of microarray-based prognostic prediction. Cancer Res 2006; 66: 2970-9.
19. Kurai M, Shiozawa T, Shih HC, Miyamoto T, Feng YZ, Kashima H, et al. Expression of Aurora kinases A and B in normal, hyperplastic, and malignant human endometrium: Aurora B as a predictor for poor prognosis in endometrial carcinoma. Human Pathol 2005; 36: 1281-8.
20. Ota T, Suto S, Katayama H, Han ZB, Suzuki F, Maeda M, et al. Increased mitotic phosphorylation of histone H3 attributable to AIM- 1/Aurora-B overexpression contributes to chromosome number instability. Cancer Res 2002; 62: 5168-77.
21. Mountzios G, Terpos E, Dimopoulos MA. Aurora kinases as targets for cancer therapy. Cancer Treat Rev 2008; 34: 175-82.
22. Harrington EA, Bebbington D, Moore J, Rasmussen RK, Ajose-Adeogun AO, Nakayama T, et al. VX-680, a potent and selective small-molecule inhibitor of the Aurora kinases, suppresses tumor growth in vivo. Nat Med 2004; 10: 262-7.
23. Fancelli D, Moll J, Varasi M, Bravo R, Artico R, Berta D, et al. 1,4,5,6- tetrahydropyrrolo[3,4-c] pyrazoles: Identification of a potent aurora kinase inhibitor with a favorable antitumor kinase inhibition profile. J Med Chem 2006; 49: 7247-51.
24. Mortlock AA, Foote KM, Heron NM, Jung FH, Pasquet G, Lohmann JJM, et al. Discovery, synthesis, and in vivo activity of a new class of pyrazoloquinazolines as selective inhibitors of aurora B kinase. J Med Chem 2007; 50: 2213-24.
25. Foote KM, Mortlock AA, Heron NM, Jung FH, Hill GB, Pasquet G, et al. Synthesis and SAR of 1-acetanilide-4-aminopyrazole-substituted quinazolines: Selective inhibitors of Aurora B kinase with potent antitumor activity. Bioorg Med Chem Lett 2008; 18: 1904-9.
26. Cramer RD, Patterson DE, Bunce JD. Comparative Molecular-Field Analysis (Comfa). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 1988; 110: 5959-67.
27. Morshed MN, Muddassar M, Pasha FA, Cho SJ. Pharmacophore identification and validation study of CK2 inhibitors using CoMFA/CoMSIA. Chem Biol Drug Des 2009; 74: 148-158
28. Klebe G, Abraham U, Mietzner T. Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J Med Chem 1994; 37: 4130-46.
29. Pasha FA, Muddassar M, Cho SJ, Ahmad K, Beg Y. 3D and quantum QSAR of non-benzodiazepine compounds. Eur J Med Chem 2008; 43: 2361-72.
30. Muddassar M, Pasha FA, Yoo KH, Lee SH, Cho SJ. Docking and quantum mechanics-guided CoMFA analysis of b-RAF inhibitors. Bull Korean Chem Soc 2008; 29: 1499-504.
31. Pasha FA, Muddassar M, Chung HW, Cho SJ, Cho H. Hologram and 3D-quantitative structure toxicity relationship studies of azo dyes. J Mol Model 2008; 14: 293-302.
32. Jung FH, Pasquet G, Lambert-van der Brempt C, Lohmann JJM, Warin N, Renaud F, et al. Discovery of novel and potent thiazoloquinazolines as selective Aurora A and B kinase inhibitors. J Med Chem 2006; 49: 955-70.
33. SYBYL 7.3. Tripos Inc, St Louis, MO 63114, USA 2007.
34. Clark M, Cramer RD, Vanopdenbosch N. Validation of the generalpurpose tripos 5.2 Force-field. J Comput Chem 1989; 10: 982- 1012.
35. Viswanadhan VN, Ghose AK, Revankar GR, Robins RK. Atomic physicochemical parameters for 3 dimensional structure directed quantitative structure-activity relationships. 4. additional parameters for hydrophobic and dispersive interactions and their application for an automated superposition of certain naturally-occurring nucleoside antibiotics. J Chem Information Computer Sci 1989; 29: 163-72.
36. Klebe G. The use of composite crystal-field environments in molecular recognition and the de novo design of protein ligands. J Mol Biol 1994; 237: 212-35.
37. Wold S, Ruhe A, Wold H, Dunn WJ. The collinearity problem in linearregression - the partial least-squares (pls) approach to generalized inverses. Siam J Sci Statistical Comput 1984; 5: 735-43.
38. Geladi P, Xie YL, Polissar A, Hopke P. Notes on the history and nature of partial least squares (PLS) modeling. J Chemometrics 1988; 2: 231-46.
39. Cramer RD, Bunce JD, Patterson DE, Frank IE. Cross-validation, bootstrapping, and partial least-squares compared with multipleregression in conventional QSAR studies. Quant Struct-Act Relat 1988; 7: 18-25.
40. Wold S. Cross-validatory estimation of number of components in factor and principal components models. Technometrics 1978; 20: 397-405.
41. Pinto-Bazurco M, Tsakovska I, Pajeva I. QSAR and 3D QSAR of inhibitors of the epidermal growth factor receptor. Int J Quantum Chem 2006; 106: 1432-44.
42. Mortlock A, Keen NJ, Jung FH, Heron NM, Foote KM, Wilkinson RW, et al. Progress in the development of selective inhibitors of aurora kinases. Curr Top Med Chem 2005; 5: 807-21.
43. Fancelli D, Moll J. Inhibitors of Aurora kinases for the treatment of cancer. Expert Opin Ther Patents 2005; 15: 1169-82.
44. Fancelli D, Berta D, Bindi S, Cameron A, Cappella P, Carpinelli P, et al. Potent and selective aurora inhibitors identified by the expansion of a novel scaffold for protein kinase inhibition. J Med Chem 2005; 48: 3080-84.
45. Heron NM, Anderson M, Blowers DP, Breed J, Eden JM, Green S, et al. SAR and inhibitor complex structure determination of a novel class of potent and specific Aurora kinase inhibitors. Bioorg Med Chem Lett 2006; 16: 1320-23.
46. Bayliss R, Sardon T, Vernos I, Conti E. Structural basis of Aurora-A activation by TPX2 at the mitotic spindle. Mol Cell 2003; 12: 851-62.
47. Nowakowski J, Cronin CN, McRee DE, Knuth MW, Nelson CG, Pavletich NP, et al. Structures of the cancer-related aurora-A, FAK, and EphA2 protein kinases from nanovolume crystallography. Structure 2002; 10: 1659-67.
48. Cheetham GMT, Knegtel RMA, Coll JT, Renwick SB, Swenson L, Weber P, et al. Crystal structure of aurora-2, an oncogenic serine/threonine kinase. J Biol Chem 2002; 277: 42419-22.
49. Myrianthopoulos V, Magiatis P, Ferandin Y, Skaltsounis AL, Meijer L, Mikros E. An integrated computational approach to the phenomenon of potent and selective inhibition of aurora kinases B and C by a series of 7-substituted indirubins. J Med Chem 2007; 50: 4027-37.
50. Fu DH, Jiang W, Zheng JT, Zhao GY, Li Y, Yi H, et al. Jadomycin B, an Aurora-B kinase inhibitor discovered through virtual screening. Mol Cancer Ther 2008; 7: 2386-93.
51. Hennequin LF, Thomas AP, Johnstone C, Stokes ESE, Ple PA, Lohmann JJM, et al. Design and structure-activity relationship of a new class of potent VEGF receptor tyrosine kinase inhibitors. J Med Chem 1999; 42: 5369-89.
52. Hennequin LF, Stokes ESE, Thomas AP, Johnstone C, Ple PA, Ogilvie DJ, et al. Novel 4-anilinoquinazolines with C-7 basic side chains: Design and structure activity relationship of a series of potent, orally active, VEGF receptor tyrosine kinase inhibitors. J Med Chem 2002; 45: 1300-12.
53. Pandey A, Volkots DL, Seroogy JM, Rose JW, Yu JC, Lambing JL, et al. Identification of orally active, potent, and selective 4-piperazinylquinazolines as antagonists of the platelet-derived growth factor receptor tyrosine kinase family. J Med Chem 2002; 45: 3772-93.
54. Smaill JB, Rewcastle GW, Loo JA, Greis KD, Chan OH, Reyner EL, et al. Tyrosine kinase inhibitors. 17. Irreversible inhibitors of the epidermal growth factor receptor: 4-(phenylamino)quinazoline- and 4-(phenylamino)pyrido[3,2-d]- pyrimidine-6-acrylamides bearing additional solubilizing functions. J Med Chem 2000; 43: 1380-97.