The tyrosine kinase inhibitor PD153035: implication of labeling position on radiometabolites formed in vitro

Nuclear Medicine and Biology

Volumn 33, Issue 8, 2006, Pages 1005-1011

  Samén, Erik ^a   Thorell, Jan Olov ^a   Fredriksson, Anna ^a   Stone Elander, Sharon ^a  

^a KAROLINSKA UNIVERSITY HOSPITAL   (Sweden)

Author keywords

Anilinoquinazoline; Epidermal growth factor receptor; In vitro metabolism; PD153035; Positron emission tomography; Tyrosine kinase inhibitor

Indexed keywords

4 (3 BROMOANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (3 BROMOANILINO) 6,7 DIMETHOXYQUINAZOLINE C 11; DRUG METABOLITE; PROTEIN TYROSINE KINASE INHIBITOR; RADIOLIGAND; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DEALKYLATION; DRUG METABOLISM; HUMAN; HUMAN CELL; HYDROXYLATION; INCUBATION TIME; ISOTOPE LABELING; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MALE; MASS SPECTROMETRY; MOLECULAR WEIGHT; NONHUMAN; OXIDATION KINETICS; POSITRON EMISSION TOMOGRAPHY; RAT; STEREOCHEMISTRY;

ANIMALS; CARBON RADIOISOTOPES; HUMANS; ISOTOPE LABELING; MALE; PROTEIN KINASE INHIBITORS; QUINAZOLINES; RADIOPHARMACEUTICALS; RATS; RATS, SPRAGUE-DAWLEY; RECEPTOR, EPIDERMAL GROWTH FACTOR; SPECIES SPECIFICITY;

EID: 33751246440     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2006.09.008     Document Type: Article

References (41)

1. Bazley L.A., and Gullick W.J. The epidermal growth factor receptor family. Endocr Relat Cancer 12 (2005) S17-S27
2. Nicholson R.I., Gee J.M., and Harper M.E. EGFR and cancer prognosis. Eur J Cancer 37 Suppl 4 (2001) S9-S15
3. Fry D.W. Mechanism of action of erbB tyrosine kinase inhibitors. Exp Cell Res 284 (2003) 131-139
4. Mulholland G.K., Winkle W., Mock B.H., and Sledge G. Radioiodinated epidermal growth factor receptor ligands as tumor probes. Dramatic potentiation of binding to MDA-468 cancer cells in presence of EGF. J Nucl Med 36 (1995) P71
5. 11C]PD153035, a selective EGF receptor tyrosine kinase inhibitor. J Labelled Compd Radiopharm 41 (1998) 623-629
6. Mulholland G.K., Zheng Q.H., Winkle W.L., and Carlson K.A. Synthesis and biodistribution of new C-11 and F-18 labeled epidermal growth factor receptor ligands. J Nucl Med 38 (1997) P141
7. 11C-labeled PD153035 in rats without and with neuroblastoma implants. Life Sci 65 (1999) 165-174
8. Lim J.K., Riese D.J., Negash K., Hawkins R.A., and VanBrocklin H.F. Synthesis and in vitro evaluation of epidermal growth factor receptor tyrosine kinase inhibitors. J Nucl Med 39 Suppl (1998) 20P-21P
9. 18F]fluorobenzylamino)-6,7-diethoxyquinazoline: a positron emitting radioprobe for the epidermal growth factor receptor. J Labelled Compd Radiopharm 42 (1999) S693-S695
10. 125I]iodoanilino)-6,7-dialkoxyquinazolines: radiolabeled epidermal growth factor receptor tyrosine kinase inhibitors. J Labelled Compd Radiopharm 43 (2000) 1183-1191
11. 11C]Iressa as a new potential PET cancer imaging agent for epidermal growth factor receptor tyrosine kinase. Bioorg Med Chem Lett 16 (2006) 4102-4106
12. 18F-labeled biomarkers for epidermal growth factor receptor tyrosine kinase. Nucl Med Biol 28 (2001) 359-374
13. 11C]acryloyl chloride. Appl Radiat Isot 58 (2003) 209-217
14. Ortu G., Ben-David I., Rozen Y., Freedman N.M.T., Chisin R., Levitzki A., et al. Labeled EGFr-TK irreversible inhibitor (ML03): in vitro and in vivo properties, potential as PET biomarker for cancer and feasibility as anticancer drug. Int J Cancer 101 (2002) 360-370
15. Shaul M., Abourbeh G., Jacobson O., Rozen Y., Laky D., Levitzki A., et al. Novel iodine-124 labeled EGFR inhibitors as potential PET agents for molecular imaging in cancer. Bioorg Med Chem 12 (2004) 3421-3429
16. Mishani E., Abourbeh G., Rozen Y., Jacobson O., Laky D., Ben I., et al. Novel carbon-11 labeled 4-dimethylamino-but-2-enoic acid [4-(phenylamino)-quinazoline-6-yl]-amides: potential PET bioprobes for molecular imaging of EGFR-positive tumors. Nucl Med Biol 31 (2004) 469-476
17. VanBrocklin H.F., Lim J.K., Coffing S.L., Hom D.L., Negash K., Ono M.Y., et al. Anilinodialkoxyquinazolines: screening epidermal growth factor receptor tyrosine kinase inhibitors for potential tumor imaging probes. J Med Chem 48 (2005) 7445-7456
18. 18F]fluoroanilino)quinazoline: a prospective irreversible EGFR binding probe. J Labelled Compd Radiopharm 48 (2005) 109-115
19. Mishani E., Abourbeh G., Jacobson O., Dissoki S., Ben Daniel R., Rozen Y., et al. High-affinity epidermal growth factor receptor (EGFR) irreversible inhibitors with diminished chemical reactivities as positron emission tomography (PET)-imaging agent candidates of EGFR overexpressing tumors. J Med Chem 48 (2005) 5337-5348
20. Dissoki S., Laky D., and Mishani E. Fluorine-18 labeling of ML04 - presently the most promising irreversible inhibitor candidate for visualization of EGFR in cancer. J Labelled Compd Radiopharm 49 (2006) 533-543
21. Logan J. Graphical analysis of PET data applied to reversible and irreversible tracers. Nucl Med Biol 27 (2000) 661-670
22. Meyer J.H., and Ichise M. Modeling of receptor ligand data in PET and SPECT imaging: a review of major approaches. J Neuroimag 11 (2001) 30-39
23. Eckelman W.C. The application of receptor theory to receptor-binding and enzyme-binding oncologic radiopharmaceuticals. Nucl Med Biol 21 (1994) 759-769
24. Eckelman W.C. Sensitivity of new radiopharmaceuticals. Nucl Med Biol 25 (1998) 169-173
25. Fry D.W., Kraker A.J., McMichael A., Ambroso L.A., Nelson J.M., Leopold W.R., et al. A specific inhibitor of the epidermal growth factor receptor tyrosine kinase. Science 265 (1994) 1093-1095
26. Bos M., Mendelsohn J., Kim Y.M., Albanell J., Fry D.W., and Baselga J. PD153035, a tyrosine kinase inhibitor, prevents epidermal growth factor receptor activation and inhibits growth of cancer cells in a receptor number-dependent manner. Clin Cancer Res 3 (1997) 2099-2106
27. Kunkel M.W., Hook K.E., Howard C.T., Przybranowski S., Roberts B.J., Elliott W.L., et al. Inhibition of the epidermal growth factor receptor tyrosine kinase by PD153035 in human A431 tumors in athymic nude mice. Invest New Drugs 13 (1996) 295-302
28. Lee S.Y., Choe Y.S., Kim D.H., Park B.N., Kim S.E., Choi Y., et al. A simple and efficient in vitro method for metabolism studies of radiotracers. Nucl Med Biol 28 (2001) 391-395
29. Rewcastle G.W., Denny W.A., Bridges A.J., Zhou H., Cody D.R., McMichael A., et al. Tyrosine kinase inhibitors. 5. Synthesis and structure-activity relationships for 4-[(phenylmethyl)amino]- and 4-(phenylamino)quinazolines as potent adenosine 5′-triphosphate binding site inhibitors of the tyrosine kinase domain of the epidermal growth factor receptor. J Med Chem 38 (1995) 3482-3487
30. Pandey A., Volkots D.L., Seroogy J.M., Rose J.W., Yu J.C., Lambing J.L., 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 45 (2002) 3772-3793
31. Fredriksson A., and Stone-Elander S. Rapid microwave-assisted cleavage of methyl phenyl ethers: new method for synthesizing desmethyl precursors and for removing protecting groups. J Labelled Compd Radiopharm 45 (2002) 529-538
32. Beedham C. The role of non-P450 enzymes in drug oxidation. Pharm World Sci 19 (1997) 255-263
33. Peiris D.M., Lam W., Michael S., and Ramanathan R. Distinguishing N-oxide and hydroxyl compounds: impact of heated capillary/heated ion transfer tube in inducing atmospheric pressure ionization source decompositions. J Mass Spectrom 39 (2004) 600-606
34. Tong W., Chowdhury S.K., Chen J.C., Zhong R., Alton K.B., and Patrick J.E. Fragmentation of N-oxides (deoxygenation) in atmospheric pressure ionization: investigation of the activation process. Rapid Commun Mass Spectrom 15 (2001) 2085-2090
35. Bickel M.H. The pharmacology and biochemistry of N-oxides. Pharmacol Rev 21 (1969) 325-355
36. Li A.P., Kaminski D.L., and Rasmussen A. Substrates of human hepatic cytochrome P450 3A4. Toxicology 104 (1995) 1-8
37. Yuan R., Madani S., Wei X.X., Reynolds K., and Huang S.M. Evaluation of cytochrome P450 probe substrates commonly used by the pharmaceutical industry to study in vitro drug interactions. Drug Metab Dispos 30 (2002) 1311-1319
38. Tracy T.S., Marra C., Wrighton S.A., Gonzales F.J., and Korzekwa K.R. Involvement of multiple cytochrome P450 isoforms in naproxen O-demethylation. Eur J Clin Pharmacol 52 (1997) 293-298
39. Uckun F.M., Thoen J., Chen H., Sudbeck E., Mao C., Malaviya R., Liu X.P., and Chen C.L. CYP1A-mediated metabolism of the Janus kinase-3 inhibitor 4-(4′-hydroxyphenyl)-amino-6,7-dimethoxyquinazoline: structural basis for inactivation by regioselective O-demethylation. Drug Metab Dispos 30 (2002) 74-85
40. McKillop D., McCormick A.D., Miles G.S., Phillips P.J., Pickup K.J., Bushby N., et al. In vitro metabolism of gefitinib in human liver microsomes. Xenobiotica 34 (2004) 983-1000
41. McKillop D., Hutchison M., Partridge E.A., Bushby N., Cooper C.M., Clarkson-Jones J.A., et al. Metabolic disposition of gefitinib, an epidermal growth factor receptor tyrosine kinase inhibitor, in rat, dog and man. Xenobiotica 34 (2004) 917-934