Molecular targeting of protein kinases to optimize selectivity and resistance profiles of kinase inhibitors

Current Topics in Medicinal Chemistry

Volumn 7, Issue 14, 2007, Pages 1332-1335

  Liao, Jeffrey Jie Lou ^a  

^a TransTech Pharma Inc   (United States)

Author keywords

CML; Drug resistant mutation; Iimatinib; Protein kinase; Protein kinase inhibitor; Selectivity; Systematic structural analysis

Indexed keywords

ABELSON KINASE; ALANINE; CD135 ANTIGEN; CYCLOPROPANECARBOXYLIC ACID [4 [4 (4 METHYL 1 PIPERAZINYL) 6 (5 METHYL 2H PYRAZOL 3 YLAMINO) 2 PYRIMIDINYLTHIO]PHENYL]AMIDE; DASATINIB; IMATINIB; NILOTINIB; PLATELET DERIVED GROWTH FACTOR RECEPTOR; PROTEIN KINASE; PROTEIN KINASE C; PROTEIN KINASE INHIBITOR; PROTEIN TYROSINE KINASE; STEM CELL FACTOR RECEPTOR; SUNITINIB; THREONINE; VALINE; VASCULOTROPIN RECEPTOR;

CHRONIC MYELOID LEUKEMIA; CLINICAL TRIAL; CRYSTAL STRUCTURE; DRUG APPROVAL; DRUG BINDING; DRUG PROTEIN BINDING; DRUG RESEARCH; DRUG SAFETY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG TARGETING; ENZYME CONFORMATION; ENZYME INHIBITION; ENZYME STRUCTURE; FOOD AND DRUG ADMINISTRATION; GENE MUTATION; HUMAN; KIDNEY CARCINOMA; REVIEW; SIGNAL TRANSDUCTION; X RAY CRYSTALLOGRAPHY; BINDING SITE; CHEMISTRY; DRUG EFFECT; DRUG RESISTANCE; METABOLISM; PROTEIN BINDING; STRUCTURE ACTIVITY RELATION;

BINDING SITES; DRUG RESISTANCE, NEOPLASM; HUMANS; LEUKEMIA, MYELOID, CHRONIC; PROTEIN BINDING; PROTEIN KINASE INHIBITORS; PROTEIN KINASES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34548825702     PISSN: 15680266     EISSN: None     Source Type: Journal    
DOI: 10.2174/156802607781696800     Document Type: Review

References (24)

1. Zimmermann, J.; Caravatti, G.; Mett, H.; Meyer, T.; Muller, M.; Lydon, N. B.; Fabbro, D. Phenylamino-pyrimidine (PAP) derivatives: A new class of potent and selective inhibitors of protein kinase C (PKC). Arch. Pharm. 1996, 329, 371-376.
2. Hunter, T. 1001 protein kinases redux-towards 2000. Semin. Cell Biol. 1994, 5, 367-376.
3. Manning, G.; Whyte, D. B.; Martinez, R.; Hunter, T.; Sudarsanam, S. The protein kinase complement of the human genome. Science 2002 298, 1912-1916, 1933-1934.
4. Stehelen, D.; Varmus, H. E.; Bishop, J. M.; Vogt, P. K. DNA related to the tranforming gene(s) of avian sarcoma viruses is present in normal avian DNA. Nature 1976, 260, 170-173.
5. Brugge, J. S.; Erikson, R. C. Identification of a transformation-specific antigen induced by an avian sarcoma virus. Nature 1977, 69, 346-348.
6. Liao J. J.; Andrews, R. C. Targeting protein multiple conformations: A structure-based approach for design of kinase inhibitors. Curr. Top. Med. Chem. 2007.
7. (a) Heisterkamp, N.; Stephenson, J. R.; Groffen, J.; Hansen, P. F. de Klein, A.; Bartram, C. R.; Grosveld, G. Localization of the c-abl oncogene adjacent to a translocation break point in chronic myelocytic leukaemia. Nature 1983, 306, 239-242;
8. (b) Sattler M.; Griffin, J. D. Molecular mechanisms of transformation by the BCR-ABL oncogene. Semin. Hematol. 2003, 40, 4-10.
9. (a) Zimmermann, J.; Buchdunger, E.; Mett, H.; Meyer, T.; Lydon, N.B.; Traxler, P. Phenylamino-pyrimidine (PAP) - derivatives: A new class of potent and highly selective PDGF-receptor autophosphorylation inhibitors. Bioorg. Med. Chem. Lett. 1996, 6, 1221-1226
10. (b) Zimmermann, J.; Buchdunger, E.; Mett, H.; Meyer, T.; Lydon, N.B. Potent and selective inhibitors of the Abl-kinase: phenylamino-pyrimidine (PAP) derivatives. Bioorg. Med. Chem. Lett. 1997, 7, 187-192.
11. Capdeville, R.; Buchdunger, E.; Zimmermann, J.; Matter, A. Glivec (STI571, imatinib), a rationally developed, targeted anticancer drug. Nat. Rev. Drug Discov. 2002, 1, 493-502.
12. Schindler, T.; Bornmann, W.; Pellicena, P.; Miller, W. T.; Clarkson, B.; Kuriyan, J. Structural mechanism for STI-571inhibition of Abelson tyrosine kinase. Science 2000, 289, 1938-1942.
13. Nagar, B.; Bornmann, W. G.; Pellicena, P.; Schindler, T.; Veach, D. R.; Miller, W. T.; Clarkson, B.; Kuriyan, J. Crystal structures of the kinase domain of c-Abl in complex with the small molecule inhibitors PD173955 and imatinib (Sti-571). Cancer Res. 2002, 62 4236-4243.
14. Liao, J. J. Molecular recognition of protein kinase binding pockets for design of potent and selective kinase inhibitors. J. Med. Chem. 2007, 50, 409-424.
15. Hubbard, S. R.; Wei, L.; Ellis, L.; Hendrickson, W. A. Crystal structure of the tyrosine kinase domain of the human insulin receptor. Nature 1994, 372, 746-754.
16. Mol, C. D.; Dougan, D. R.; Schneider, T. R.; Skene, R. J.; Kraus, M. L.; Scheibe, D. N.; Snell, G. P.; Zou, H.; Sang, B. C.; Wilson, K. P. Structural basis for the autoinhibition and STI-571 inhibition of c-Kit tyrosine kinase. J. Biol. Chem. 2004, 279, 31655-31663.
17. Mendel, D. B.; Laird, A. D.; Xin, X.; Louie, S. G.; Christensen, J. G.; Li, G.; Schreck, R. E.; Abrams, T. J.; Ngai, T. J.; Lee, L. B.; Murray, L. J.; Carver, J.; Chan, E.; Moss, K. G.; Haznedar, J. O,; Sukbuntherng, J,; Blake, R. A.; Sun, L.; Tang, C.; Miller, T.; Shirazian, S. ; McMahon, G.; Cherrington, J. M. In vivo antitumor activity of SU11248, a novel tyrosine kinase inhibitor targeting vascular endothelial growth factor and platelet-derived growth factor receptors: Determination of a pharmacokinetic/pharmacodynamic relationship. Clin. Cancer Res. 2003, 9, 327-337.
18. Faivre, S.; Delbaldo, C.; Vera, K.; Robert, C.; Lozahic, S.; Lassau, N.; Bello, C.; Deprimo, S.; Brega, N.; Massimini, G.; Armand, J. P.; Scigalla, P.; Raymond, E. Safety, pharmacokinetic, and antitumor activity of SU11248, a novel oral multitarget tyrosine kinase inhibitor, in patients with cancer. J. Clin. Oncol. 2006, 24, 25-35.
19. Levinson N. M.; Kuchment, O.; Shen, K.; Young, M. A.; Koldobskiy, M.; Karplus, M.; Cole, P. A.; Kuriyan, J.A Src-like inactive conformation in the abl tyrosine kinase domain. PLoS Biol. 2006, 4, 0753-0767.
20. Burgess, M. R.; Skaggs, B. J.; Shah, N. P.; Lee, F. Y.; Sawyers, C. L. Comparative analysis of two clinically active BCR-ABL kinase inhibitors reveals the role of conformation-specific binding in resistance. Proc. Natl. Acad. Sci. 2005, 102, 3395-3400.
21. Azam M.; Nardi, V.; Shakespeare, W. C.; Metcalf, C. A. 3rd; Bohacek, R. S.; Wang, Y.; Sundaramoorthi, R.; Sliz, P.; Veach, D. R.; Bornmann, W. G.; Clarkson, B.; Dalgarno, D. C.; Sawyer, T. K.; Daley, G. Q. Activity of dual SRC-ABL inhibitors highlights the role of BCR/ABL kinase dynamics in drug resistance. Proc. Natl. Acad. 2006, 103 9244-9249.
22. O'Hare, T.; Corbin, A. S.; Druker, B. J. Targeted CML therapy: controlling drug resistance, seeking cure. Curr. Opin. Genet Dev. 2006, 16, 92-99.
23. Tibes, R.; Giles,F.; McQueen,T.; Bergstrom, D. A.; Freedman, S. J.; Leukemia, M. A. Translational in vivo and in vitro studies in patients (pts) with acute myeloid leukemia (AML), chronic myeloid leukemia (CML) and myeloproliferative disease (MPD) treated with MK-0457 (MK), a novel Aurora kinase, Flt3, JAK2, and Bcr-Abl Inhibitor. Blood 2006, 10, Abstract 1362.
24. Adrian, F. J.; Ding, Q.; Sim, T.; Velentza, A.; Sloan, C.; Liu, Y.; Zhang, G.; Hur, W.; Ding, S.; Manley, P.; Mestan, J.; Fabbro, D.; Gray, N. S. Allosteric inhibitors of Bcr-abl-dependent cell proliferation. Nat. Chem. Biol. 2006, 2, 95-102.