Structural basis of Src tyrosine kinase inhibition with a new class of potent and selective trisubstituted purine-based compounds

Chemical Biology and Drug Design

Volumn 67, Issue 1, 2006, Pages 46-57

  Dalgarno, David ^a   Stehle, Thilo ^b   Narula, Surinder ^a   Schelling, Pierre ^b   Van Schravendijk, Marie Rose ^a   Adams, Susan ^a   Andrade, Lawrence ^a   Keats, Jeff ^a   Ram, Mary ^a   Jin, Lei ^c   Grossman, Trudy ^a   MacNeil, Ian ^a   Metcalf III, Chester ^a   Shakespeare, William ^a   Wang, Yihan ^a   Keenan, Terry ^a   Sundaramoorthi, Raji ^a   Bohacek, Regine ^a   Weigele, Manfred ^a   Sawyer, Tomi ^a  

^a ARIAD PHARMACEUTICALS INC   (United States)

^b MASSACHUSETTS GENERAL HOSPITAL   (United States)

^c SUNTORY LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

[4 [2 CYCLOPENTYL 9 (3 HYDROXYPHENETHYL)PURIN 6 YLAMINO]PHENYL]DIMETHYLPHOSPHINE OXIDE; AP 23451; FUNCTIONAL GROUP; PROTEIN TYROSINE KINASE; PROTEIN TYROSINE KINASE INHIBITOR; PURINE ANTAGONIST; PURVALANOL A; PURVALANOL B; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ANIMAL CELL; ARTICLE; BINDING AFFINITY; CANCER; CARBOXY TERMINAL SEQUENCE; CLINICAL OBSERVATION; COMPLEX FORMATION; CONTROLLED STUDY; CORRELATION ANALYSIS; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG MECHANISM; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG SPECIFICITY; DRUG STRUCTURE; ENZYME INHIBITION; ENZYME SPECIFICITY; ENZYME STRUCTURE; ESCHERICHIA COLI; LEPIDOPTERA; METASTASIS; MOTION; NONHUMAN; OSTEOLYSIS; PRIORITY JOURNAL; PROTEIN DOMAIN; QUANTUM YIELD; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

ADENINE; ADENOSINE TRIPHOSPHATE; BONE AND BONES; CARBON; CATALYTIC DOMAIN; CYCLIN-DEPENDENT KINASE 2; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; LIGANDS; LYMPHOCYTE SPECIFIC PROTEIN TYROSINE KINASE P56(LCK); MODELS, MOLECULAR; NEOPLASMS; NITROGEN; PHOSPHONIC ACIDS; PROTEIN CONFORMATION; PURINES; PYRIMIDINES; SRC-FAMILY KINASES; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 33745080292     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2005.00316.x     Document Type: Article

References (45)

1. Thomas S.M. Brugge J.S. ( 1997) Cellular functions regulated by Src family kinases. Annu Rev Cell Dev Biol 13 : 513 609.
2. Sawyer T. Boyce B. Dalgarno D. Iuliucci J. ( 2001) Src inhibitors: genomics to therapeutics. Expert Opin Investig Drugs 10 : 1327 1344.
3. Summy J.M. Gallick G.E. ( 2003) Src family kinases in tumor progression and metastasis. Cancer Metastasis Rev 22 : 337 358.
4. Warmuth M. Damoiseaux R. Liu Y. Fabbro D. Gray N. ( 2003) SRC family kinases: potential targets for the treatment of human cancer and leukemia. Curr Pharm Des 9 : 2043 2059.
5. Brugge J.S. Erikson R.L. ( 1977) Identification of a transformation- specific antigen induced by an avian sarcoma virus. Nature 269 : 346 348.
6. Soriano P. Montgomery C. Geske R. Bradley A. ( 1991) Targeted disruption of the c-src proto-oncogene leads to osteopetrosis in mice. Cell 64 : 693 702.
7. Marzia M. Sims N.A. Voit S. Migliaccio S. Taranta A. Bernardini S. Faraggiana T. Yoneda T. Mundy G.R. Boyce B.F. Baron R. Teti A. ( 2000) Decreased c-Src expression enhances osteoblast differentiation and bone formation. J Cell Biol 151 : 311 320.
8. Amling M. Neff L. Priemel M. Schilling A.F. Rueger J.M. Baron R. ( 2000) Progressive increase in bone mass and development of odontomas in aging osteopetrotic c-src-deficient mice. Bone 27 : 603 610.
9. Sawyer T.K. ( 2004) Cancer metastasis therapeutic targets and drug discovery: emerging small-molecule protein kinase inhibitors. Expert Opin Investig Drugs 13 : 1 19.
10. Eliceiri B.P. Paul R. Schwartzberg P.L. Hood J.D. Leng J. Cheresh D.A. ( 1999) Selective requirement for Src kinases during VEGF-induced angiogenesis and vascular permeability. Mol Cell 4 : 915 924.
11. Sawyer T.K. Bohacek R.S. Metcalf C.A. III. Shakespeare W.C. Wang Y. Sundaramoorthi R. Keenan T. Narula S. Weigele M. Dalgarno D.C. ( 2003) Novel protein kinase inhibitors: SMART drug design technology. Biotechniques 2-10 ( Suppl. 12 15.
12. Schindler T. Sicheri F. Pico A. Gazit A. Levitzki A. Kuriyan J. ( 1999) Crystal structure of Hck in complex with a Src family-selective tyrosine kinase inhibitor. Mol Cell 3 : 639 648.
13. Zhu X. Kim J.L. Newcomb J.R. Rose P.E. Stover D.R. Toledo L.M. Zhao H. Morgenstern K.A. ( 1999) Structural analysis of the lymphocyte-specific kinase Lck in complex with non-selective and Src family selective kinase inhibitors. Structure Fold Des 7 : 651 661.
14. Yamaguchi H. Hendrickson W.A. ( 1996) Structural basis for activation of human lymphocyte kinase Lck upon tyrosine phosphorylation. Nature 384 : 484 489.
15. Xu W. Doshi A. Lei M. Eck M.J. Harrison S.C. ( 1999) Crystal structures of c-Src reveal features of its autoinhibitory mechanism. Mol Cell 3 : 629 638.
16. Sicheri F. Moarefi I. Kuriyan J. ( 1997) Crystal structure of the Src family tyrosine kinase Hck. Nature 385 : 602 609.
17. Cowan-Jacob S.W. Fendrich G. Manley P.W. Jahnke W. Fabbro D. Liebetanz J. Meyer T. ( 2005) The crystal structure of a c-Src complex in an active conformation suggests possible steps in c-Src activation. Structure (Camb) 13 : 861 871.
18. Breitenlechner C.B. Kairies N.A. Honold K. Scheiblich S. Koll H. Greiter E. Koch S. Schafer W. Huber R. Engh R.A. ( 2005) Crystal structures of active SRC kinase domain complexes. J Mol Biol 353 : 222 231.
19. Gray N.S. Wodicka L. Thunnissen A.M. Norman T.C. Kwon S. Espinoza F.H. Morgan D.O. Barnes G. LeClerc S. Meijer L. ( 1998) Exploiting chemical libraries, structure, and genomics in the search for kinase inhibitors. Science 281 : 533 558.
20. Sielecki T.M. Boylan J.F. Benfield P.A. Trainor G.L. ( 2000) Cyclin-dependent kinase inhibitors: useful targets in cell cycle regulation. J Med Chem 43 : 1 18.
21. Chang Y.T. Gray N.S. Rosania G.R. Sutherlin D.P. Kwon S. Norman T.C. Sarohia R. Leost M. Meijer L. Schultz P.G. ( 1999) Synthesis and application of functionally diverse 2,6,9-trisubstituted purine libraries as CDK inhibitors. Chem Biol 6 : 361 375.
22. Hardcastle I.R. Golding B.T. Griffin R.J. ( 2002) Designing inhibitors of cyclin-dependent kinases. Annu Rev Pharmacol Toxicol 42 : 325 348.
23. De Azevedo W.F. Leclerc S. Meijer L. Havlicek L. Strnad M. Kim S.H. ( 1997) Inhibition of cyclin-dependent kinases by purine analogues: crystal structure of human cdk2 complexed with roscovitine. Eur J Biochem 243 : 518 526.
24. Bohacek R.S. McMartin C. ( 1997) Modern computational chemistry and drug discovery: structure generating programs. Curr Opin Chem Biol 1 : 157 161.
25. Wang Y. Metcalf C.A. Shakespeare W.C. Sundaramoorthi R. Keenan T.P. Bohacek R.S. van Schravendijk Violette S.M. Naruala S.S. Dalgarno D.C. Haraldson C. Keats J. Liou S. Mani U. Pradeepan S., et al. ( 2003) Bone-targeted 2,6,9-trisubstituted purines: novel inhibitors of Src tyrosine kinase for the treatment of bone diseases. Bioorg Med Chem Lett 13 : 3067 3070.
26. O'Hare T. Pollock R. Stoffregen E.P. Keats J.A. Abdullah O.M. Moseson E.M. Rivera V.M. Tang H. Metcalf III. C.A. Bohacek R.S. Wang Y. Sundaramoorthi R. Shakespeare W.C. Dalgarno D. Clarkson T., et al. ( 2004) Inhibition of wild-type and mutant Bcr-Abl by AP23464, a potent ATP-based oncogenic protein kinase inhibitor: implications for CML. Blood 104 : 2532 2539.
27. Corbin A.S. Demehri S. Griswold I.J. Wang Y. Metcalf C.A. III. Sundaramoorthi R. Shakespeare W.C. Snodgrass J. Wardwell S. Dalgarno D. Luliucci J. Sawyer T.K. Heinrich M.C. Druker B.J. Deininger M.W. ( 2005) In vitro and in vivo activity of ATP-based kinase inhibitors AP23464 and AP23848 against activation-loop mutants of kit. Blood 106 : 227 234.
28. Brunton V.G. Avizienyte E. Fincham V.J. Serrels B. Metcalf C.A. III. Sawyer T.K. Frame M.C. ( 2005) Identification of Src-specific phosphorylation site on focal adhesion kinase: dissection of the role of Src SH2 and catalytic functions and their consequences for tumor cell behavior. Cancer Res 65 : 1335 1342.
29. Sicheri F. Kuriyan J. ( 1997) Structures of Src-family tyrosine kinases. Curr Opin Struct Biol 7 : 777 785.
30. Xu W. Harrison S.C. Eck M.J. ( 1997) Three-dimensional structure of the tyrosine kinase c-Src. Nature 385 : 595 602.
31. Buchanan S. ( 2003) Protein structure: discovering selective protein kinase inhibitors. Targets 2 : 101 108.
32. Chuaqui C. Deng Z. Singh J. ( 2005) Interaction profiles of protein kinase-inhibitor complexes and their application to virtual screening. J Med Chem 48 : 121 133.
33. Jones T.A. Zou J.Y. Cowan S.W. Kjeldgaard M. ( 1991) Improved methods for building protein models in electron density maps and the location of errors in these models. Acta Crystallogr A 47 ( Pt 2 110 119.
34. Hubbard S.R. Wei L. Ellis L. Hendrickson W.A. ( 1994) Crystal structure of the tyrosine kinase domain of the human insulin receptor. Nature 372 : 746 754.
35. Altmann E. Widler L. Missbach M. ( 2002) N (7)-substituted-5-aryl- pyrrolo[2,3-d]pyrimidines represent a versatile class of potent inhibitors of the tyrosine kinase c-Src. Mini Rev Med Chem 2 : 201 208.
36. Hennequin L.F. Thomas A.P. Johnstone C. Stokes E.S. Plé P.A. Lohmann J.J. Ogilvie D.J. Dukes M. Wedge S.R. Curwen J.O. Kendrew J. Lambert-van der Brempt C. ( 1999) Design and structure-activity relationship of a new class of potent VEGF receptor tyrosine kinase inhibitors. J Med Chem 42 : 5369 5389.
37. Wang J. Morin P. Wang W. Kollman P.A. ( 2001) Use of MM-PBSA in reproducing the binding free energies to HIV-1 RT of TIBO derivatives and predicting the binding mode to HIV-1 RT of efavirenz by docking and MM-PBSA. J Am Chem Soc 123 : 5221 5230.
38. Zhu L. Wehmeyer R. Rieke R.D. ( 1991) The direct formation of functionalized alkyl (aryl)zinc halides by oxidative addition of highly reactive zinc with organic halides and their reactions with acid chlorides and their reactions with acid chlorides, a,b-unsaturated ketones and allylic, aryl and vinyl halides. J Org Chem 56 : 1445 1453.
39. Negishi E. King A.O. Okukado N. ( 1976) Selective carbon-carbon bond formation via transition metal catalysis. 3. A highly selective synthesis of unsymmetrical biaryls and diarylmethanes by the nicket or palladium-catalyzed reaction of aryl- and benzylzinc derivatives with aryl halides. J Org Chem 42 : 1821 1822.
40. Otwinowski Z. Minor W., editors ( 1997) Processing of X-Ray Diffraction Data Collected in Oscillation Mode. New York, NY : Academic Press.
41. Collaborative Computational Project No. 4 ( 1994) The CCP4 suite: programs for protein crystallography. Acta Crystallogr D50 : 760 763.
42. Brunger A.T. Kuriyan J. Karplus M. ( 1987) Crystallographic R factor refinement by molecular dynamics. Science 235 : 458 460.
43. Berman H.M. Battistuz T. Bhat T.N. Bluhm W.F. Bourne P.E. Burkhardt K. Feng Z. Gilliland G.L. Iype L. Jain S. Fagan P. Marvin J. Padilla D. Ravichandran V. Schneider B. ( 2002) The Protein Data Bank. Acta Crystallogr D Biol Crystallogr 58 ( Pt 6 No 1 899 907.
44. Brunger A. ( 1992) Free R value: a novel statistical quantity for assessing the accuracy of crystal structures. Nature 355 : 472 475.
45. Carson M. ( 1987) Ribbon models of macromolecules. J Mol Graph 5 : 103 106.