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Discovery of a potent and selective aurora kinase inhibitor.

Oslob JD, Romanowski MJ, Allen DA, Baskaran S, Bui M, Elling RA, Flanagan WM, Fung AD, Hanan EJ, Harris S, Heumann SA, Hoch U, Jacobs JW, Lam J, Lawrence CE, McDowell RS, Nannini MA, Shen W, Silverman JA, Sopko MM, Tangonan BT, Teague J, Yoburn JC, Yu CH, Zhong M, Zimmerman KM, O'Brien T, Lew W
Bioorg Med Chem Lett 18 4880-4 (2008)
Cited: 55 times
EuropePMC logo PMID: 18678489

Abstract

This communication describes the discovery of a novel series of Aurora kinase inhibitors. Key SAR and critical binding elements are discussed. Some of the more advanced analogues potently inhibit cellular proliferation and induce phenotypes consistent with Aurora kinase inhibition. In particular, compound 21 (SNS-314) is a potent and selective Aurora kinase inhibitor that exhibits significant activity in pre-clinical in vivo tumor models.

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  1. A molecular mechanics approach to modeling protein-ligand interactions: relative binding affinities in congeneric series. Rapp C, Kalyanaraman C, Schiffmiller A, Schoenbrun EL, Jacobson MP. J Chem Inf Model 51 2082-2089 (2011)
  2. The human Aurora kinase inhibitor danusertib is a lead compound for anti-trypanosomal drug discovery via target repurposing. Ochiana SO, Pandarinath V, Wang Z, Kapoor R, Ondrechen MJ, Ruben L, Pollastri MP. Eur J Med Chem 62 777-784 (2013)
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Reviews citing this publication (16)

  1. AXL receptor tyrosine kinase as a promising anti-cancer approach: functions, molecular mechanisms and clinical applications. Zhu C, Wei Y, Wei X. Mol Cancer 18 153 (2019)
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  3. Aurora-A Kinase: A Potent Oncogene and Target for Cancer Therapy. Yan M, Wang C, He B, Yang M, Tong M, Long Z, Liu B, Peng F, Xu L, Zhang Y, Liang D, Lei H, Subrata S, Kelley KW, Lam EW, Jin B, Liu Q. Med Res Rev 36 1036-1079 (2016)
  4. Aurora kinase inhibitors as anticancer molecules. Katayama H, Sen S. Biochim Biophys Acta 1799 829-839 (2010)
  5. Aurora kinase inhibitors in preclinical and clinical testing. Cheung CH, Coumar MS, Hsieh HP, Chang JY. Expert Opin Investig Drugs 18 379-398 (2009)
  6. Functions of Aurora kinase C in meiosis and cancer. Quartuccio SM, Schindler K. Front Cell Dev Biol 3 50 (2015)
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  8. Second-Generation Antimitotics in Cancer Clinical Trials. Novais P, Silva PMA, Amorim I, Bousbaa H. Pharmaceutics 13 1011 (2021)
  9. Spindle Assembly Checkpoint as a Potential Target in Colorectal Cancer: Current Status and Future Perspectives. Diogo V, Teixeira J, Silva PM, Bousbaa H. Clin Colorectal Cancer 16 1-8 (2017)
  10. Advances in Aurora kinase inhibitor patents. Coumar MS, Cheung CH, Chang JY, Hsieh HP. Expert Opin Ther Pat 19 321-356 (2009)
  11. Therapeutic Targeting of the Gas6/Axl Signaling Pathway in Cancer. Tanaka M, Siemann DW. Int J Mol Sci 22 9953 (2021)
  12. ENMD-2076 for hematological malignancies. How J, Yee K. Expert Opin Investig Drugs 21 717-732 (2012)
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  14. Maintaining Genome Stability in Defiance of Mitotic DNA Damage. Ferrari S, Gentili C. Front Genet 7 128 (2016)
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  16. Aurora B Inhibitors as Cancer Therapeutics. Kovacs AH, Zhao D, Hou J. Molecules 28 3385 (2023)

Articles citing this publication (33)

  1. The discovery of the potent aurora inhibitor MK-0457 (VX-680). Bebbington D, Binch H, Charrier JD, Everitt S, Fraysse D, Golec J, Kay D, Knegtel R, Mak C, Mazzei F, Miller A, Mortimore M, O'Donnell M, Patel S, Pierard F, Pinder J, Pollard J, Ramaya S, Robinson D, Rutherford A, Studley J, Westcott J. Bioorg Med Chem Lett 19 3586-3592 (2009)
  2. Update on Aurora Kinase Targeted Therapeutics in Oncology. Green MR, Woolery JE, Mahadevan D. Expert Opin Drug Discov 6 291-307 (2011)
  3. Rationalizing tight ligand binding through cooperative interaction networks. Kuhn B, Fuchs JE, Reutlinger M, Stahl M, Taylor NR. J Chem Inf Model 51 3180-3198 (2011)
  4. SNS-314, a pan-Aurora kinase inhibitor, shows potent anti-tumor activity and dosing flexibility in vivo. Arbitrario JP, Belmont BJ, Evanchik MJ, Flanagan WM, Fucini RV, Hansen SK, Harris SO, Hashash A, Hoch U, Hogan JN, Howlett AR, Jacobs JW, Lam JW, Ritchie SC, Romanowski MJ, Silverman JA, Stockett DE, Teague JN, Zimmerman KM, Taverna P. Cancer Chemother Pharmacol 65 707-717 (2010)
  5. A dynamic mechanism for allosteric activation of Aurora kinase A by activation loop phosphorylation. Ruff EF, Muretta JM, Thompson AR, Lake EW, Cyphers S, Albanese SK, Hanson SM, Behr JM, Thomas DD, Chodera JD, Levinson NM. Elife 7 e32766 (2018)
  6. Quantitative conformational profiling of kinase inhibitors reveals origins of selectivity for Aurora kinase activation states. Lake EW, Muretta JM, Thompson AR, Rasmussen DM, Majumdar A, Faber EB, Ruff EF, Thomas DD, Levinson NM. Proc Natl Acad Sci U S A 115 E11894-E11903 (2018)
  7. Comparing sixteen scoring functions for predicting biological activities of ligands for protein targets. Xu W, Lucke AJ, Fairlie DP. J Mol Graph Model 57 76-88 (2015)
  8. Development and biological evaluation of a novel aurora A kinase inhibitor. Sardon T, Cottin T, Xu J, Giannis A, Vernos I. Chembiochem 10 464-478 (2009)
  9. Targeting high Aurora kinases expression as an innovative therapy for hepatocellular carcinoma. Liu F, Wang G, Wang X, Che Z, Dong W, Guo X, Wang Z, Chen P, Hou D, Zhang Q, Zhang W, Pan Y, Yang D, Liu H. Oncotarget 8 27953-27965 (2017)
  10. Dual Inhibition of AKT and MEK Pathways Potentiates the Anti-Cancer Effect of Gefitinib in Triple-Negative Breast Cancer Cells. You KS, Yi YW, Cho J, Seong YS. Cancers (Basel) 13 1205 (2021)
  11. Identification of signalling cascades involved in red blood cell shrinkage and vesiculation. Kostova EB, Beuger BM, Klei TR, Halonen P, Lieftink C, Beijersbergen R, van den Berg TK, van Bruggen R. Biosci Rep 35 e00187 (2015)
  12. The multiple roles of computational chemistry in fragment-based drug design. Law R, Barker O, Barker JJ, Hesterkamp T, Godemann R, Andersen O, Fryatt T, Courtney S, Hallett D, Whittaker M. J Comput Aided Mol Des 23 459-473 (2009)
  13. 2-Aminobenzimidazoles as potent Aurora kinase inhibitors. Zhong M, Bui M, Shen W, Baskaran S, Allen DA, Elling RA, Flanagan WM, Fung AD, Hanan EJ, Harris SO, Heumann SA, Hoch U, Ivy SN, Jacobs JW, Lam S, Lee H, McDowell RS, Oslob JD, Purkey HE, Romanowski MJ, Silverman JA, Tangonan BT, Taverna P, Yang W, Yoburn JC, Yu CH, Zimmerman KM, O'Brien T, Lew W. Bioorg Med Chem Lett 19 5158-5161 (2009)
  14. Identification, SAR studies, and X-ray co-crystallographic analysis of a novel furanopyrimidine aurora kinase A inhibitor. Coumar MS, Tsai MT, Chu CY, Uang BJ, Lin WH, Chang CY, Chang TY, Leou JS, Teng CH, Wu JS, Fang MY, Chen CH, Hsu JT, Wu SY, Chao YS, Hsieh HP. ChemMedChem 5 255-267 (2010)
  15. Prediction of biological activity of Aurora-A kinase inhibitors by multilinear regression analysis and support vector machine. Yan A, Chong Y, Wang L, Hu X, Wang K. Bioorg Med Chem Lett 21 2238-2243 (2011)
  16. Water-soluble prodrugs of an Aurora kinase inhibitor. Oslob JD, Heumann SA, Yu CH, Allen DA, Baskaran S, Bui M, Delarosa E, Fung AD, Hashash A, Hau J, Ivy S, Jacobs JW, Lew W, Maung J, McDowell RS, Ritchie S, Romanowski MJ, Silverman JA, Yang W, Zhong M, Fuchs-Knotts T. Bioorg Med Chem Lett 19 1409-1412 (2009)
  17. Discovery of a Potent, Injectable Inhibitor of Aurora Kinases Based on the Imidazo-[1,2-a]-Pyrazine Core. Yu T, Tagat JR, Kerekes AD, Doll RJ, Zhang Y, Xiao Y, Esposite S, Belanger DB, Curran PJ, Mandal AK, Siddiqui MA, Shih NY, Basso AD, Liu M, Gray K, Tevar S, Jones J, Lee S, Liang L, Ponery S, Smith EB, Hruza A, Voigt J, Ramanathan L, Prosise W, Hu M. ACS Med Chem Lett 1 214-218 (2010)
  18. Advances in fragment-based drug discovery platforms. Orita M, Warizaya M, Amano Y, Ohno K, Niimi T. Expert Opin Drug Discov 4 1125-1144 (2009)
  19. Classification of Aurora kinase inhibitors by self-organizing map (SOM) and support vector machine (SVM). Yan A, Nie X, Wang K, Wang M. Eur J Med Chem 61 73-83 (2013)
  20. Aurora kinases as druggable targets in pediatric leukemia: heterogeneity in target modulation activities and cytotoxicity by diverse novel therapeutic agents. Jayanthan A, Ruan Y, Truong TH, Narendran A. PLoS One 9 e102741 (2014)
  21. 3D-QSAR and molecular docking studies on derivatives of MK-0457, GSK1070916 and SNS-314 as inhibitors against Aurora B kinase. Zhang B, Li Y, Zhang H, Ai C. Int J Mol Sci 11 4326-4347 (2010)
  22. A sensitive and selective liquid chromatography/tandem mass spectrometry method for determination of MLN8237 in human plasma. Lipsitz E, Moorthy G, Mosse Y, Fox E, Adamson PC. J Chromatogr B Analyt Technol Biomed Life Sci 878 2369-2373 (2010)
  23. Discovery of 4-aminoquinazoline--urea derivatives as Aurora kinase inhibitors with antiproliferative activity. Cai J, Li L, Hong KH, Wu X, Chen J, Wang P, Cao M, Zong X, Ji M. Bioorg Med Chem 22 5813-5823 (2014)
  24. Discovery of BPR1K871, a quinazoline based, multi-kinase inhibitor for the treatment of AML and solid tumors: Rational design, synthesis, in vitro and in vivo evaluation. Hsu YC, Coumar MS, Wang WC, Shiao HY, Ke YY, Lin WH, Kuo CC, Chang CW, Kuo FM, Chen PY, Wang SY, Li AS, Chen CH, Kuo PC, Chen CP, Wu MH, Huang CL, Yen KJ, Chang YI, Hsu JT, Chen CT, Yeh TK, Song JS, Shih C, Hsieh HP. Oncotarget 7 86239-86256 (2016)
  25. A New Quantitative Cell-Based Assay Reveals Unexpected Microtubule Stabilizing Activity of Certain Kinase Inhibitors, Clinically Approved or in the Process of Approval. Ramirez-Rios S, Michallet S, Peris L, Barette C, Rabat C, Feng Y, Fauvarque MO, Andrieux A, Sadoul K, Lafanechère L. Front Pharmacol 11 543 (2020)
  26. Application of shape-based and pharmacophore-based in silico screens for identification of Type II protein kinase inhibitors. Mucs D, Bryce RA, Bonnet P. J Comput Aided Mol Des 25 569-581 (2011)
  27. Exploring new structural features of the 4-[(3-methyl-4-aryl-2,3-dihydro-1,3-thiazol-2-ylidene)amino]benzenesulphonamide scaffold for the inhibition of human carbonic anhydrases. Distinto S, Meleddu R, Ortuso F, Cottiglia F, Deplano S, Sequeira L, Melis C, Fois B, Angeli A, Capasso C, Angius R, Alcaro S, Supuran CT, Maccioni E. J Enzyme Inhib Med Chem 34 1526-1533 (2019)
  28. Identification of new novel scaffold for Aurora A inhibition by pharmacophore modeling and virtual screening. Chavan SR, Dash RC, Alam MS, Hirwani RR. Mol Divers 18 853-863 (2014)
  29. Click approach to the discovery of 1,2,3-triazolylsalicylamides as potent Aurora kinase inhibitors. Song D, Park Y, Yoon J, Aman W, Hah JM, Ryu JS. Bioorg Med Chem 22 4855-4866 (2014)
  30. Design, synthesis, and evaluation of hinge-binder tethered 1,2,3-triazolylsalicylamide derivatives as Aurora kinase inhibitors. Jeong Y, Lee J, Ryu JS. Bioorg Med Chem 24 2114-2124 (2016)
  31. Classification of Aurora-A Kinase Inhibitors Using Self-Organizing Map (SOM) and Support Vector Machine (SVM). Wang L, Wang Z, Yan A, Yuan Q. Mol Inform 30 35-44 (2011)
  32. High-Throughput Assay to Screen Small Molecules for Their Ability to Prevent Sickling of Red Blood Cells. Nakagawa A, Cooper MK, Kost-Alimova M, Berstler J, Yu B, Berra L, Klings ES, Huang MS, Heeney MM, Bloch DB, Zapol WM. ACS Omega 7 14009-14016 (2022)
  33. Synthesis of some novel thieno[3,2-d]pyrimidines as potential cytotoxic small molecules against breast cancer. Kandeel M, Abdelhameid MK, Eman K, Labib MB. Chem Pharm Bull (Tokyo) 61 637-647 (2013)


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