Radiohalogenated 4-anilinoquinazoline-based EGFR-TK inhibitors as potential cancer imaging agents

Nuclear Medicine and Biology

Volumn 39, Issue 2, 2012, Pages 247-260

  Neto, Carina ^a   Fernandes, Célia ^a   Oliveira, Maria Cristina ^a   Gano, Lurdes ^a   Mendes, Filipa ^a   Kniess, Torsten ^b   Santos, Isabel ^a  

^a INSTITUTO TECNOLÓGICO E NUCLEAR   (Portugal)

^b INSTITUTE OF ION BEAM PHYSICS AND MATERIALS RESEARCH   (Germany)

Author keywords

4 Anilinoquinazolines; EGFR TK inhibitors; Fluorine 18; Iodine 125; PET; Radiohalogenation; SPECT

Indexed keywords

4 ANILINOQUINAZOLINE DERIVATIVE; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE INHIBITOR; FLUORINE 18; IODINE 125; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]QUINAZOLINE 6 YL] 3 (TRIMETHYLSTANNYL)BENZAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]QUINAZOLINE 6 YL] 3 IODOBENZAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]QUINAZOLINE 6 YL] 4 (TRIMETHYLSTANNYL)BENZAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]QUINAZOLINE 6 YL] 4 DIMETHYLAMINOBENZAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]QUINAZOLINE 6 YL] 4 FLUOROBENZAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]QUINAZOLINE 6 YL] 4 IODOBENZAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]QUINAZOLINE 6 YL] 4 NITROBENZAMIDE; N [4 [(3 CHLORO 4 FLUOROPHENYL)AMINO]QUINAZOLINE 6 YL] 4 TRIMETHYLAMMONIUM BENZAMIDE TRIFLUOROMETHANESULFONATE; PLASMA PROTEIN; QUINAZOLINE DERIVATIVE; SODIUM IODIDE; TRIMETHYLAMMONIUM SALT DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; AUTOPHOSPHORYLATION; CELL ASSAY; CELL PROLIFERATION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONTROLLED STUDY; DESTANNYLATION; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG EXCRETION; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; FLUORINATION; HALOGENATION; HUMAN; HUMAN CELL; IC 50; INTESTINE; IODINATION; ISOTOPE LABELING; LIPOPHILICITY; LIVER; MUSCLE; NUCLEOPHILIC SUBSTITUTION REACTION; STILLE REACTION; SUBSTITUTION REACTION; THYROID GLAND; URINARY TRACT; WESTERN BLOTTING;

ANIMALS; CELL LINE, TUMOR; FEMALE; FLUORINE RADIOISOTOPES; HALOGENATION; HUMANS; IODINE RADIOISOTOPES; MICE; PHOSPHORYLATION; PROTEIN-TYROSINE KINASES; QUINAZOLINES; RECEPTOR, EPIDERMAL GROWTH FACTOR; TISSUE DISTRIBUTION; VULVAR NEOPLASMS;

EID: 84856346831     PISSN: 09698051     EISSN: 18729614     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2011.09.001     Document Type: Article

References (40)

1. Laskin J.J., Sandler A.B. Epidermal growth factor receptor: a promising target in solid tumours. Cancer Treat Rev 2004, 30:1-17.
2. Bublil E.M., Yarden Y. The EGF receptor family: spearheading a merger of signalling and therapeutics. Curr Opin Cell Biol 2007, 19:124-134.
3. Herst R.S. Review of epidermal growth factor receptor biology. Int J Radiat Oncol Biol Phys 2004, 59:21-26.
4. Levitzki A. Protein kinase inhibitors as a therapeutic modality. Acc Chem Res 2003, 36:462-469.
5. Noble M.E.M., Endicott J.A., Johnson L.N. Protein kinase inhibitors: insights into drug design from structure. Science 2004, 303:1800-1805.
6. Tibes R., Trent J., Kurzrock R. Tyrosine kinase inhibitors and the dawn of molecular cancer therapeutics. Ann Rev Pharm Toxicol 2005, 45:357-384.
7. Workman P. Genomics and the second golden era of cancer drug development. Mol Biosyst 2005, 1:17-26.
8. Breza N., Pato' J., Orfi L., Hegymegi-Barakonyi B., Anhegyi P.B., Varkondi E., et al. Synthesis and characterization of novel quinazoline type inhibitors for mutant and wild-type EGFR and RICK kinases. J Recept Signal Transduct 2008, 28:361-373.
9. Allen L.F., Eiseman I.A., Fry D.W., Lenehan P.F. CI-1033, an irreversible pan-erbB receptor inhibitor and its potential application for the treatment of breast cancer. Semin Oncol 2003, 30:65-78.
10. Arora A., Scholar E.M. Role of tyrosine kinase inhibitors in cancer therapy. J Pharmacol Exp Ther 2005, 315:971-999.
11. Montemurro F., Valabrega G., Aglietta M. Lapatinib: a dual inhibitor of EGFR and HER2 tyrosine kinase activity. Expert Opin Biol Ther 2007, 7(2):257-268.
12. Medina P.J., Goodin S. Lapatinib: a dual inhibitor of human epidermal growth factor receptor tyrosine kinases. Clin Ther 2008, 30(8):1426-1447.
13. Albanell J., Gascón P. Small molecules with EGFR-TK inhibitor activity. Curr Drug Targets 2005, 6:259-274.
14. Bikker J.A., Brooijmans N., Wissner A., Mansour T.S. Kinase domain mutations in cancer. Implications for small molecule drug design strategies. J Med Chem 2009, 52:1493-1509.
15. 124I-labeled small molecular tracer and Positron emission tomography. Mol Imaging Biol 2006, 8:262-277.
16. Mishani E., Abourbeh G. Cancer molecular imaging: radionuclide-based biomarkers of the epidermal growth factor receptor (EGFR). Curr Top Med Chem 2007, 7:1755-1772.
17. Mishani E., Abourbeh G., Eiblmaier M., Anderson C.J. Imaging of EGFR and EGFR tyrosine kinase overexpression in tumors by nuclear medicine modalities. Curr Pharm Des 2008, 14:2983-2998.
18. Gelovani J.G. Molecular imaging of epidermal growth factor receptor expression-activity at the kinase level in tumors with positron emission tomography. Cancer Metastasis Rev 2008, 27:645-653.
19. Pantaleo M.A., Nannini M., Maleddu A., Fanti S., Ambrosini V., Nanni C., et al. Conventional and novel PET tracers for imaging in oncology in the era of molecular therapy. Cancer Treat Rev 2008, 34:103-121.
20. Pantaleo M.A., Nannini M., Maleddu A., Fanti S., Nanni C., Boschi S., et al. Experimental results and related clinical implications of PET detection of epidermal growth factor receptor (EGFr) in cancer. Ann Oncol 2009, 20:213-226.
21. Hicks J.W., VanBrocklin H.F., Wilson A.A., Sylvain H., Vasdev N. Radiolabeled small molecule protein kinase inhibitors for imaging with PET or SPECT. Molecules 2010, 15:8260-8278.
22. Pantaleo M.A., Mishani E., Nanni C., Landuzzi L., Boschi S., Nicoletti G., et al. Evaluation of modified PEG-anilinoquinazoline derivatives as potential agents for EGFR imaging in cancer by small animal PET. Mol Imaging Biol 2010, 12:616-625. SPECT.
23. Fernandes C., Oliveira C., Gano L., Bourkoula A., Pirmettis I., Santos I. Radioiodination of new EGFR inhibitors as potential SPECT agents for molecular imaging of breast cancer. Bioorg Med Chem 2007, 15:3974-3980.
24. 99mTc biomarker for EGFR-TK imaging. Dalton Trans 2008, 28:3215-3225.
25. Bourkoula A., Paravatou-Petsotas M., Papadopoulos A., Santos I., Pietzsch H.J., Livaniou E., et al. Synthesis and characterization of rhenium and technetium-99m tricarbonyl complexes bearing the 4-[3-bromophenyl]quinazoline moiety as a biomarker for EGFR-TK imaging. Eur J Med Chem 2009, 44:4021-4027.
26. Garcia R., Fousková P., Gano L., Paulo A., Campello P., Toth E., et al. A quinazoline-derivative DOTA-type gallium(III) complex for targeting epidermal growth factor receptors: synthesis, characterisation and biological studies. J Biol Inorg Chem 2009, 14:261-271.
27. Garcia R., Kubicek V., Drahos B., Gano L., Santos I.C., Campello P., et al. Synthesis, characterization and biological evaluation of In(III) complexes anchored by DOTA-like chelators bearing a quinazoline moiety. Metallomics 2010, 2:571-580.
28. Hirata M., Kanai Y., Naka S., Matsumuro K., Kagawa S., Mitsuyoshi Y., et al. Evaluation of radioiodinated quinazoline derivative as a new ligand for EGF receptor tyrosine kinase activity using SPECT. Ann Nucl Med 2011, 25:117-124.
29. Bonasera T.A., Ortu G., Rozen Y., Krais R., Freedman N.M., Chisin R., et al. Potential (18)F-labeled biomarkers for epidermal growth factor receptor tyrosine kinase. Nucl Med Biol 2001, 28:359-374.
30. Ortu G., Ben-David B., Rozen Y., Freedman N.M.T., Chisin R., Levitski 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 2002, 101:360-370.
31. 11C]acryloyl chloride. Appl Radiat Isot 2003, 58:209-217.
32. 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 2004, 12:3421-3429.
33. Mishani E., Abourbeh G., Rozen Y., Jacobson O., Laky D., Ben D.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 2004, 31:469-476.
34. Mishani E., Abourbeh G., Rozen Y., Jacobson O., Dissoki S., Daniel R.B., 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 2005, 48:5337-5348.
35. Dissoki S., Laky D., Mishani E. Fluorine-18 labeling of ML04 - presently the most promising irreversible inhibitor candidate for visualization of EGFR in cancer. J Labelled Comp Radiopharm 2006, 49:533-543.
36. 18F]SFB). Appl Radiat Isot 2005, 63:329-332.
37. 131I]-2-(4-iodophenylamino) pyrido[2,3-d]pyrimidin-7-one radiolabeled Abl kinase inhibitors. Nucl Med Biol 2005, 32:313-321.
38. Minick D., Frenz J., Patrick M., Brent D. A comprehensive method for determining hydrophobicity constants by reversed phase high-performance liquid chromatography. J Med Chem 1988, 31:1923-1933.
39. H.H. Coenen, Fluorine-18 labelling methods: features and possibilities of basic reactions. In: P.A. Schubiger, L. Lehmann, M. Friebe, editors. PET chemistry - the driving force in molecular medicine. Ernst Schering Research Foundation Workshop 62, Springer: Berlin, Heidelberg, New York: 2007, p. 15-50.
40. Eisenwiener K.-P., Prata M.I.M., Buschmann I., Zhang H.-W., Santos A.C., Wenger S., et al. Bioconjugate Chem 2002, 13:530-541.