Novel iodine-124 labeled EGFR inhibitors as potential PET agents for molecular imaging in cancer

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 13, 2004, Pages 3421-3429

  Shaul, Mazal ^a   Abourbeh, Galith ^a   Jacobson, Orit ^a   Rozen, Yulia ^a   Laky, Desideriu ^a   Levitzki, Alexander ^a   Mishani, Eyal ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

EGFR TK; Iodine 124; Molecular imaging; PET

Indexed keywords

6 AMINO 4 (3 TRIBUTYLSTANNYLAMINO)QUINAZOLINE; ACETAMIDE DERIVATIVE; AMIDE; EPIDERMAL GROWTH FACTOR RECEPTOR; IODINE 124; METHYL GROUP; RADIOISOTOPE; UNCLASSIFIED DRUG;

ARTICLE; DRUG EFFECT; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; IMAGING SYSTEM; ISOTOPE LABELING; MOLECULAR MECHANICS; POSITRON EMISSION TOMOGRAPHY;

CELL LINE, TUMOR; ENZYME INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; IODINE RADIOISOTOPES; MOLECULAR STRUCTURE; NEOPLASMS; POSITRON-EMISSION TOMOGRAPHY; RECEPTOR, EPIDERMAL GROWTH FACTOR;

EID: 2942549775     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.04.044     Document Type: Article

References (25)

1. Artega C.L. The epidermal growth factor receptor: from mutant oncogene in nonhuman cancers to therapeutic target in human neoplasia. J. Clin. Oncol. 19:2001;32
2. Ritter C., Arteaga C.L. The epidermal growth factor receptor-tyrosine kinase: a promising therapeutic target in solid tumors. Semin. Oncol. 30:2003;3
3. Raymond E., Faivre S., Armand J.P. Epidermal growth factor receptor tyrosine kinase as a target for anticancer therapy. Drugs. 60:2000;15
4. Salomon D.S., Brandt R., Ciardiello F., Normanno N. Epidermal growth factor-related peptides and their receptors in human malignancies. Crit. Rev. Oncol. Hematol. 19:1995;183
5. Voldborg B.R., Damstrup L., Spang-Thomsen M., Poulsen H.S. Epidermal growth factor receptor (EGFR) and EGFR mutations, function and possible role in clinical trials. Ann. Oncol. 8:1997;1197
6. Walsh J.C., Maclean D., Northrop J., Padgett H., Ysaguirre T. A combinatorial strategy for the design and synthesis of 18F-labeled quinoline derivatives as kinase imaging agents. J. Labelled Compd. Radiopharm. 46:2003;S48
7. VanBrocklin H.F., Dorff P.N., Vasdev N., O'Neil J.P., Nandanan E., Gibbs A.R. Synthesis of 2′-, 3′- and 4′-[F18] fluoroanilinoquinazoline. J. Labelled Compd. Radiopharm. 46:2003;S117
8. Ackermann U., Tochon-Dabguy H., Nice E., Nerrie M., Young K., Sachinidis J., Scott A. Synthesis, radiolabelling and biological evaluation of derivatives of the P210BCR-ABL tyrosine kinase inhibitor AG957. J. Labelled Compd. Radiopharm. 46:2003;S118
9. Kesarios N., Tochon-Danguy H.-J., Ackermann U., Sachinidis J., Lambert J., Nerrie M., Nice E., Scott A. Synthesis and radiolabelling of a tyrosine kinase inhibitor of erbB2/neu (HER2) receptors. J. Labelled Compd. Radiopharm. 46:2003;S119
10. Mishani E., Bonasera T.A., Rozen Y., Ortu G., Gazit A., Levitzki A. Fluorinated EGFR-TK inhibitors-based tracers for PET. J. Labelled Compd. Radiopharm. 42:1999;S27
11. Mishani E., Abourbeh G., Ortu G., Rozen Y., Ben-David I., Froimovaci S., Dissoki S., Gazit A., Levitzki A. Novel EGFR irreversible tyrosine kinase inhibitor candidates for the diagnostic and therapeutic treatment of cancer. J. Labelled Compd. Radiopharm. 46:2003;S115
12. Mishani E., Abourbeh G., Rozen Y., Laki D., Levitzki A. Carbon-11 labeling of 4-dimethylamino-but-2-enoic acid [4-(phenylamino)-quinazoline-6-yl]- amides. A new class of EGFR irreversible inhibitors. J. Labelled Compd. Radiopharm. 46:2003;S2
13. Bonasera T.A., Ortu G., Rozen Y., Krais R., Freedman N.M., Chisin R., Gazit A., Levitzki A., Mishani E. Potential (18)F-labeled biomarkers for epidermal growth factor receptor tyrosine kinase. Nucl. Med. Biol. 28:2001;359
14. Ortu G., Ben-David I., Rozen Y., Freedman N.M.T., Chisin R., Levitzki A., Mishani E. Labeled EGFRTK 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
15. Ben-David I., Rozen Y., Ortu G., Mishani E. Radiosynthesis of ML03, a novel positron emission tomography biomarker for targeting epidermal growth factor receptor via the labeling synthon: [C-11]acryloyl chloride. Appl. Radiat. Isot. 58:2003;209
16. Eschmann S.M., Reischl G., Bilger K., Kupferschlager J., Thelen M.H., Dohmen B.M., Besenfelder H., Bares R. Evaluation of dosimetry of radioiodine therapy in benign and malignant thyroid disorders by means of iodine-124 and PET. Eur. J. Nucl. Med. Mol. Imaging. 29:2002;760
17. 124I]Iodo-2′- deoxyuridine for functional PET imaging of cell proliferation. Nucl. Med. Biol. 25:1998;359
18. 124I in patients with breast cancer. Int. J. Cancer. 47:1991;344
19. Flower M.A., al-Saadi A., Harmer C.L., McCready V.R., Ott R.J. Dose response study on thyrotoxic patients undergoing PET and radioiodine therapy. Eur. J. Nucl. Med. 21:1994;531-536
20. Roelcke U. I-124 Iododeoxyuridine retention in peritumoral edema of glioblastomas. J. Neuro-Oncol. 35:1997;S38
21. Stoscheck C.M., Carpenter G. Characterization of the metabolic turnover of epidermal growth factor receptor protein in A-431 cells. J. Cell. Physiol. 120:1984;296
22. Tsou H.R., Mamuya N., Johnson B.D., Reich M.F., Gruber B.C., Ye F., Nilakantan R., Chen R., Descafani C., De Blanc R., Davis R., Koehn F.E., Greenberger L.M., Wang Y.F., Wissner A. 6-Substituted-4-(3-bromophenylamino) quinazolines as putative irreversible inhibitors of the epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor (HER-2) tyrosine kinases with enhanced antitumor activity. J. Med. Chem. 44:2001;2719
23. Smaill J.B., Palmer B.D., Rewcastle G.W., Denny A., McNamara D.J., Dobrusin E.M., Bridges A.J., Zhou H., Hollis Showalter H.D., Winters R.T., Leopold W.R., Fry D.W., Nelson J.M., Slintal V., Elliot W.L., Roberts B.J., Vincent P.W., Patmore Tyrosine kinase inhibitors. 15. 4-(phenylamino)quinazoline and 4-(phenylamino)pyrido[d]pyrimidine acrylamides as irreversible inhibitors of ATP binding site of the epidermal growth factor receptor. J. Med. Chem. 42:1999;1803
24. 125I]N- (diethylaminoethyl)-4-iodobenzamide: a potential ligand for imaging malignant melanoma. Nucl. Med. Biol. 20:1993;75
25. Elderfield R.C., Williamson T.A., Gensler W.J., Kremer C.B. J. Org. Chem. 12:1947;405