Synthesis and in vitro examination of [124I]-, [ 125I]- and [131I]-2-(4-iodophenylamino) pyrido[2,3-d]pyrimidin-7-one radiolabeled Abl kinase inhibitors

Nuclear Medicine and Biology

Volumn 32, Issue 4, 2005, Pages 313-321

  Veach, Darren R ^a   Namavari, Mohammad ^a   Beresten, Tatiana ^a   Balatoni, Julius ^a,b   Minchenko, Maria ^a   Djaballah, Hakim ^a   Finn, Ronald D ^a   Clarkson, Bayard ^a   Gelovani, Juri G ^a,b   Bornmann, William G ^a,b   Larson, Steven M ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b UNIVERSITY OF TEXAS   (United States)

Author keywords

Iodine 124; Iodine 125; Iodine 131; Iododestannylation; Pyridopyrimidinone; Tyrosine kinase inhibitor

Indexed keywords

4 IODOPHENYLPYRIDOPYRIMIDINONE; 4 IODOPHENYLPYRIDOPYRIMIDINONE I 131; 4' TRI N BUTYLSTANNYLPYRIDOPYRIMIDINONE; 4' TRIMETHYLSTANNYLPYRIDOPYRIMIDINONE; 6 (2,6 DICHLOROPHENYL) 2 (4 IODOPHENYLAMINO) 8 METHYL 8H PYRIDO[2,3 D]PYRIMIDIN 7 ONE I 124; 6 (2,6 DICHLOROPHENYL) 2 (4 IODOPHENYLAMINO) 8 METHYL 8H PYRIDO[2,3 D]PYRIMIDIN 7 ONE I 125; 6 (2,6 DICHLOROPHENYL) 2 (4 IODOPHENYLAMINO) 8 METHYL 8H PYRIDO[2,3 D]PYRIMIDIN 7 ONE I 131; ABELSON KINASE INHIBITOR; ACETIC ACID; BROMIDE; DIOXANE; HYDROGEN PEROXIDE; PALLADIUM; PHOSPHOTRANSFERASE INHIBITOR; PYRIMIDINONE DERIVATIVE; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

ARTICLE; CANCER INHIBITION; CELL PROLIFERATION; CONTROLLED STUDY; DRUG SYNTHESIS; DRUG UPTAKE; ENZYME ACTIVITY; GROWTH INHIBITION; HUMAN; HUMAN CELL; IC 50; ISOTOPE LABELING; MICROWAVE RADIATION; RADIOIODINATION;

CARCINOMA, SQUAMOUS CELL; CELL LINE, TUMOR; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; IODINE RADIOISOTOPES; LEUKEMIA, MYELOID, CHRONIC; METABOLIC CLEARANCE RATE; PROTEIN-TYROSINE KINASES; PYRIMIDINES; RADIOPHARMACEUTICALS;

EID: 21044433151     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2005.01.008     Document Type: Article

References (45)

1. J.F. Dorsey, R. Jove, A.J. Kraker, and J. Wu The pyrido[2,3-d]pyrimidine derivative PD180970 inhibits p210Bcr-Abl tyrosine kinase and induces apoptosis of K562 leukemic cells Cancer Res 60 2000 3127 3131
2. D. Wisniewski, C.L. Lambek, C. Liu, A. Strife, D.R. Veach, and B. Nagar Characterization of potent inhibitors of the Bcr-Abl and the c-kit receptor tyrosine kinases Cancer Res 62 2002 4244 4255
3. A.J. Kraker, B.G. Hartl, A.M. Amar, M.R. Barvian, H.D. Showalter, and C.W. Moore Biochemical and cellular effects of c-Src kinase-selective pyrido[2, 3-d]pyrimidine tyrosine kinase inhibitors Biochem Pharmacol 60 2000 885 898
4. S. Faderl, M. Talpaz, Z. Estrov, S. O'Brien, R. Kurzrock, and H.M. Kantarjian The biology of chronic myeloid leukemia N Engl J Med 341 1999 164 172
5. M. Deininger, E. Buchdunger, and B.J. Druker The development of imatinib as a therapeutic agent for chronic myeloid leukemia Blood 2004 [electronic publication ahead of print]
6. B.J. Druker, S. Tamura, E. Buchdunger, S. Ohno, G.M. Segal, and S. Fanning Effects of a selective inhibitor of the Abl tyrosine kinase on the growth of Bcr-Abl positive cells Nat Med 2 1996 561 566
7. E. Buchdunger, J. Zimmermann, H. Mett, T. Meyer, M. Muller, and B.J. Druker Inhibition of the Abl protein-tyrosine kinase in vitro and in vivo by a 2-phenylaminopyrimidine derivative Cancer Res 56 1996 100 104
8. D.A. Tuveson, N.A. Willis, T. Jacks, J.D. Griffin, S. Singer, and C.D. Fletcher STI571 inactivation of the gastrointestinal stromal tumor c-KIT oncoprotein: biological and clinical implications Oncogene 20 2001 5054 5058
9. C.D. Blanke, B.L. Eisenberg, and M.C. Heinrich Gastrointestinal stromal tumors Curr Treat Options Oncol 2 2001 485 491
10. A. Hochhaus, and T. Hughes Clinical resistance to imatinib: mechanisms and implications Hematol Oncol Clin North Am 18 2004 641 656
11. P. La Rosee, A.S. Corbin, E.P. Stoffregen, M.W. Deininger, and B.J. Druker Activity of the Bcr-Abl kinase inhibitor PD180970 against clinically relevant Bcr-Abl isoforms that cause resistance to imatinib mesylate (Gleevec, STI571) Cancer Res 62 2002 7149 7153
12. D.R. Huron, M.E. Gorre, A.J. Kraker, C.L. Sawyers, N. Rosen, and M.M. Moasser A novel pyridopyrimidine inhibitor of abl kinase is a picomolar inhibitor of Bcr-abl-driven K562 cells and is effective against STI571-resistant Bcr-abl mutants Clin Cancer Res 9 2003 1267 1273
13. N. von Bubnoff, D.R. Veach, W.T. Miller, W. Li, J. Sanger, and C. Peschel Inhibition of wild-type and mutant Bcr-Abl by pyrido-pyrimidine-type small molecule kinase inhibitors Cancer Res 63 2003 6395 6404
14. A.J. Tipping, S. Baluch, D.J. Barnes, D.R. Veach, B.M. Clarkson, and W.G. Bornmann Efficacy of dual-specific Bcr-Abl and Src-family kinase inhibitors in cells sensitive and resistant to imatinib mesylate Leukemia 18 2004 1352 1356
15. T. O'Hare, R. Pollock, E.P. Stoffregen, J.A. Keats, O.M. Abdullah, and E.M. Moseson Inhibition of wild-type and mutant Bcr-Abl by AP23464, a potent ATP-based oncogenic protein kinase inhibitor: implications for CML Blood 104 2004 2532 2539
16. D.H. Boschelli Dual inhibitors of Src and Abl tyrosine kinases Drug Des Rev 1 2004 203 214
17. F. Giles, H. Kantarjian, B. Wassmann, J. Cortes, S. O'Brien, and C. Tanaka A phase I/II study of AMN107, a novel aminopyrimidine inhibitor of Bcr-Abl, on a continuous daily dosing schedule in adult patients with imatinib-resistant advanced phase chronic myeloid leukemia (CML) or relapsed/refractory Philadelphia chromosome (Ph+) acute lymphocytic leukemia (ALL) Blood 104 2004 10a 11a
18. N.P. Shah, C. Tran, F.Y. Lee, P. Chen, D. Norris, and C.L. Sawyers Overriding imatinib resistance with a novel ABL kinase inhibitor Science 305 2004 399 401
19. B. Nagar, W.G. Bornmann, P. Pellicena, T. Schindler, D.R. Veach, and W.T. Miller Crystal structures of the kinase domain of c-Abl in complex with the small molecule inhibitors PD173955 and imatinib (STI-571) Cancer Res 62 2002 4236 4243
20. A.J. O'Neill, T.G. Cotter, J.M. Russell, and E.F. Gaffney Abl expression in human fetal and adult tissues, tumours, and tumour microvessels J Pathol 183 1997 325 329
21. A.M. Pendergast The Abl family kinases: mechanisms of regulation and signaling Adv Cancer Res 85 2002 51 100
22. M. Wetzler, M. Talpaz, R.A. Van Etten, C. Hirsh-Ginsberg, M. Beran, and R. Kurzrock Subcellular localization of bcr-Abl, and bcr-Abl proteins in normal and leukemic cells and correlation of expression with myeloid differentiation J Clin Invest 92 1993 1925 1939
23. J. Zhu, and J.Y. Wang Death by Abl: a matter of location Curr Top Dev Biol 59 2004 165 192
24. N.P. Shah, and C.L. Sawyers Mechanisms of resistance to STI571 in Philadelphia chromosome-associated leukemias Oncogene 22 2003 7389 7395
25. M.E. Gorre, M. Mohammed, K. Ellwood, N. Hsu, R. Paquette, and P.N. Rao Clinical resistance to STI-571 cancer therapy caused by BCR-ABL gene mutation or amplification Science 293 2001 876 880
26. A.A. Sandberg, and J.A. Bridge Updates on the cytogenetics and molecular genetics of bone and soft tissue tumors: chondrosarcoma and other cartilaginous neoplasms Cancer Genet Cytogenet 143 2003 1 31
27. R.E. Schmandt, R. Broaddus, K.H. Lu, H. Shvartsman, A. Thornton, and A. Malpica Expression of c-ABL, c-KIT, and platelet-derived growth factor receptor-beta in ovarian serous carcinoma and normal ovarian surface epithelium Cancer 98 2003 758 764
28. T. Yanagawa, H. Harada, S. Iwasa, K. Tabuchi, K. Omura, and H. Suzuki c-Abl expression in oral squamous cell carcinomas Oral Oncol 36 2000 89 94
29. A.Y. Tsygankov, and S.K. Shore Src: regulation, role in human carcinogenesis and pharmacological inhibitors Curr Pharm Des 10 2004 1745 1756
30. J.R. Wiener, T.C. Windham, V.C. Estrella, N.U. Parikh, P.F. Thall, and M.T. Deavers Activated SRC protein tyrosine kinase is overexpressed in late-stage human ovarian cancers Gynecol Oncol 88 2003 73 79
31. B.S. Verbeek, T.M. Vroom, S.S. AdriaansenSlot, A.E. OttenhoffKalff, J.G.N. Geertzema, and A. Hennipman c-Src protein expression is increased in human breast cancer. An immunohistochemical and biochemical analysis J Pathol 180 1996 383 388
32. M.P. Lutz, I.B. Esser, B.B. Flossmann-Kast, R. Vogelmann, H. Luhrs, and H. Friess Overexpression and activation of the tyrosine kinase Src in human pancreatic carcinoma Biochem Biophys Res Commun 243 1998 503 508
33. M.V. Yezhelyev, G. Koehl, M. Guba, T. Brabletz, K.W. Jauch, and A. Ryan Inhibition of SRC tyrosine kinase as treatment for human pancreatic cancer growing orthotopically in nude mice Clin Cancer Res 10 2004 8028 8036
34. M. Shaul, G. Abourbeh, O. Jacobsen, Y. Rozen, D. Laky, and A. Levitzki Novel iodine-124 labeled EGFR inhibitors as potential PET agents for molecular imaging in cancer Bioorg Med Chem 12 2004 3421 3429
35. S.L. Matheson, S. Mzengeza, and B.J. Jean-Claude Synthesis of 1-[4-(m-tolyl)amino-6-quinazolinyl]3-[C-14]-methyl triazene: a radiolabeled probe for the combi-targeting concept J Label Compd Radiopharm 46 2003 729 735
36. J.K. Lim, K. Negash, S.M. Hanrahan, and H.F. VanBrocklin Synthesis of 4-(3′-[I-125]iodoanilino)-6,7-dialkoxyquinazolines: radiolabeled epidermal growth factor receptor tyrosine kinase inhibitors J Label Compd Radiopharm 43 2000 1183 1191
37. P. Johnström, A. Fredriksson, J.-O. Thorell, and S. Stone-Elander Synthesis of [methoxy-C-11]PD153035, a selective EGF receptor tyrosine kinase inhibitor J Label Compd Radiopharm 41 1998 623 629
38. U. Ackermann, H.J. Tochon-Danguy, K. Young, J.I. Sachinidis, J. Gordon Chan, and A.M. Scott C-11 labelling of AG957 - a potential tyrphostin radiotracer for PET J Label Compd Radiopharm 45 2002 157 165
39. B. Nagar, O. Hantschel, M.A. Young, K. Scheffzek, D. Veach, and W. Bornmann Structural basis for the autoinhibition of c-Abl tyrosine kinase Cell 112 2003 859 871
40. M. Namavari, D.R. Veach, R.D. Finn, J. Gelovani, W. Bornmann, and S.M. Larson Radiolabeled iodopyridopyrimidinone derivatives as radiopharmaceutical probe for molecular imaging in cancer Abstract Program and abstracts for the 3rd annual meeting of the society for molecular imaging Mol Imaging 3 2004 218
41. S.R. Klutchko, J.M. Hamby, D.H. Boschelli, Z. Wu, A.J. Kraker, and A.M. Amar 2-Substituted aminopyrido[2,3-d]pyrimidin-7(8H) ones. Structure-activity relationships against selected tyrosine kinases and in vitro and in vivo anticancer activity J Med Chem 41 1998 3276 3292
42. D.H. Boschelli, Z. Wu, S.R. Klutchko, H.D. Showalter, J.M. Hamby, and G.H. Lu Synthesis and tyrosine kinase inhibitory activity of a series of 2-amino-8H-pyrido[2,3-d]pyrimidines: identification of potent, selective platelet-derived growth factor receptor tyrosine kinase inhibitors J Med Chem 41 1998 4365 4377
43. R.K. Ingham, S.D. Rosenberg, and H. Gilman Organotin compounds Chem Rev 60 1960 459 539
44. Y. Sheh, J. Koziorowski, J. Balatoni, C. Lom, J.R. Dahl, and R.D. Finn Low energy cyclotron production and chemical separation of "no carrier added" iodine-124 from a reusable, enriched tellurium-124 dioxide/aluminum oxide solid solution target Radiochim Acta 88 2000 169 173
45. D.R. Trentham, R.G. Bardsley, J.F. Eccleston, and A.G. Weeds Elementary processes of the magnesium ion-dependent adenosine triphosphatase activity of heavy meromyosin. A transient kinetic approach to the study of kinases and adenosine triphosphatases and a colorimetric inorganic phosphate assay in situ Biochem J 126 1972 635 644