A useful EGFR-TK ligand for tumor diagnosis with SPECT: Development of radioiodinated 6-(3-morpholinopropoxy)-7-ethoxy-4-(3′-iodophenoxy) quinazoline

Annals of Nuclear Medicine

Volumn 27, Issue 5, 2013, Pages 431-443

  Hirata, Masahiko ^a   Kanai, Yasukazu ^a,b   Naka, Sadahiro ^a,b   Yoshimoto, Mitsuyoshi ^c   Kagawa, Shinya ^a,d   Matsumuro, Keiji ^a   Katsuma, Hideyuki ^a   Yamaguchi, Hiroshi ^e   Magata, Yasuhiro ^e   Ohmomo, Yoshiro ^a  

^a OSAKA MEDICAL COLLEGE   (Japan)

^b OSAKA UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

^c NATIONAL CANCER CENTER HOSPITAL EAST   (Japan)

^d Shiga Medical Center   (Japan)

^e HAMAMATSU UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

EGF; Quinazoline; Radioiodine; Radiopharmaceutical; SPECT; Tyrosine kinase

Indexed keywords

2 (2 AMINO 3 METHOXYPHENYL)CHROMONE; 3,5 DI TERT BUTYL 4 HYDROXYBENZYLIDENEMALONONITRILE; 4 (3 BROMOANILINO) 6,7 DIMETHOXYQUINAZOLINE; 6 (3 DIMETHYLAMINOPROPOXY) 7 ETHOXY 4 (3' IODOPHENOXY)QUINAZOLINE I 125; 6 (3 MORPHOLINOPROPOXY) 7 ETHOXY 4 (3' IODOPHENOXY)QUINAZOLINE I 125; 6 (3 PHENYLPROPOXY) 7 ETHOXY 4 (3' IODOPHENOXY)QUINAZOLINE I 125; 6 [3 (4 METHYLPIPERAZIPROPOXY)] 7 ETHOXY 4 (3' IODOPHENOXY)QUINAZOLINE I 125; 6 BENZYLOXY 7 ETHOXY 4 (3' IODOPHENOXY)QUINAZOLINE I 125; 6 ISOIPROPOXY 7 ETHOXY 4 (3' IODOPHENOXY)QUINAZOLINE I 125; EPIDERMAL GROWTH FACTOR RECEPTOR; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE INHIBITOR; GEFITINIB; GENISTEIN; QUINAZOLINE DERIVATIVE; RADIOLIGAND; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING ASSAY; CONTROLLED STUDY; ENZYME PHOSPHORYLATION; FEASIBILITY STUDY; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; ISOTOPE LABELING; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR DIAGNOSIS;

ANIMALS; CARCINOMA, SQUAMOUS CELL; CELL LINE, TUMOR; HUMANS; IODINE RADIOISOTOPES; ISOTOPE LABELING; LIGANDS; MALE; METABOLIC CLEARANCE RATE; MICE; ORGAN SPECIFICITY; QUINAZOLINES; RADIOPHARMACEUTICALS; RECEPTOR, EPIDERMAL GROWTH FACTOR; TISSUE DISTRIBUTION; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON;

EID: 84879006904     PISSN: 09147187     EISSN: 18646433     Source Type: Journal    
DOI: 10.1007/s12149-013-0703-y     Document Type: Article

References (37)

1. Downward J, Yarden Y, Mayes E, Scrace G, Totty N, Stockwell P, et al. Close similarity of epidermal growth factor receptor and v-erb-B oncogene protein sequences. Nature. 1984;307:521-7.
2. Ullrich A, Coussens L, Hayflick JS, Dull TJ, Gray A, Tam AW, et al. Human epidermal growth factor receptor cDNA sequence and aberrant expression of the amplified gene in A431 epidermoid carcinoma cells. Nature. 1984;309:418-25.
3. Klapper LN, Kirschbaum MH, Sela M, Yarden Y. Biochemical and clinical implications of the ErbB/HER signaling network of growth factor receptors. Adv Cancer Res. 2000;77:25-79.
4. Herbst RS, Fukuoka M, Baselga J. Gefitinib-a novel targeted approach to treating cancer. Nat Rev Cancer. 2004;4:956-65.
5. McLeod HL, Brunton VG, Eckardt N, Lear MJ, Robins DJ, Workman P, et al. In vivo pharmacology and anti-tumor evaluation of the tyrphostin tyrosine kinase inhibitor RG13022. Br J Cancer. 1996;74:1714-8.
6. Croisy-Delcey M, Croisy A, Mousset S, Letourneur M, Bisagni E, Jacquemin SA, et al. Genistein analogues: effects on epidermal growth factor receptor tyrosine kinase and on stress-activated pathways. Biomed Pharmacother. 1997;51:286-94.
7. Barker AJ, Gibson KH, Grundy W, Goldfrey AA, Barlow JJ, Healy MP, et al. Genistein analogues: effects on epidermal growth factor receptor tyrosine kinase and on stress-activated pathways. Bioorg Med Chem. 2001;11:1911-4.
8. Ciardiello F, Caputo R, Bianco R, Damiano V, Fontanini G, Cuccato S, et al. Inhibition of growth factor production and angiogenesis in human cancer cells by ZD1839 (Iressa), a selective epidermal growth factor receptor tyrosine kinase inhibitor. Clin Cancer Res. 2001;7:1459-65.
9. Wakeling AE, Guy SP, Woodburn JR, Ashton SE, Curry BJ, Barker AJ, et al. ZD1839 (Iressa): an orally active inhibitor of epidermal growth factor signaling with potential for cancer therapy. Cancer Res. 2002;62:5749-54.
10. Stamos J, Sliwkowski MX, Eigenbrot C. Structure of the epidermal growth factor receptor kinase domain alone and in complex with a 4-anilinoquinazoline inhibitor. J Biol Chem. 2002;277:46265-72.
11. Grunwald V, Hidalgo M. Development of the epidermal growth factor receptor inhibitor Tarceva (OSI-774). Adv Exp Med Biol. 2003;532:235-46.
12. Fry DW, Kraker AJ, McMichael A, Ambroso LA, Nelson JM, Leopold WR, et al. A specific inhibitor of the epidermal growth factor receptor tyrosine kinase. Science. 1994;265:1093-5.
13. Kunkel MW, Hook KE, Howard CT, Roberts BJ, Elliott WL, Leopold WR. Inhibition of the epidermal growth factor receptor tyrosine kinase by PD153035 in human A431 tumors in athymic nude mice. Invest New Drugs. 1996;13:295-302.
14. 11C] PD153035, a selective EGF receptor tyrosine kinase inhibitor. J Labelled Compd Radiopharm. 1998;41:623-9.
15. Seimbille Y, Phelps ME, Czernin J, Silverman DS. Fluorine-18 labeling of 6, 7-distributed anilinoqunazoline derivatives, for positron emission tomography (PET) imaging of tyrosine kinase receptors: synthesis 18F-Iressa and related molecular probes. J Labelled Compd Radiopharm. 2005;48:819-27.
16. Mishani E, Abourbeh G, Jacobson O, Dissoki S, Daniel RB, 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. 2005;48:5337-48.
17. Abourbeh G, Dissoki S, Jacobson O, Litchi A, Ben DR, Laki D, et al. Evaluation of radiolabeled ML04, a putative irreversible inhibitor of epidermal growth factor receptor, as a bioprobe for PET imaging of EGFR-overexpressing tumors. Nucl Med Biol. 2007;34:55-70.
18. Mishani E, Abourbeh G, Rozen Y, Jacobson O, Laky D, Iris DB, 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;31:469-76.
19. Wang H, Yu J, Yang G, Song X, Sun X, Zhao S, Mu D. Assessment of 11C- labeled-4-N-(3-bromoanilino)-6, 7-dimethoxyquinazoline as a positron emission tomography agent to monitor epidermal growth factor receptor expression. Cancer Sci. 2007;98:1413-6.
20. 11C-PD153035 in humans. J Nucl Med. 2009;50:303-8.
21. Hirata M, Kanai Y, Naka S, Matsumuro K, Kagawa S, Yoshimoto M, et al. Evaluation of radioiodinated quinazoline derivative as a new ligand for EGF receptor tyrosine kinase activity using SPECT. Ann Nucl Med. 2011;25:117-24.
22. Hirata M, Kanai Y, Naka S, Matsumuro K, Kagawa S, Yoshimoto M, et al. Synthesis and evaluation of radioiodinated phenoxyquinazoline and benzylaminoquinazoline derivatives as new EGF receptor tyrosine kinase imaging ligands for tumor diagnosis using SPECT. Ann Nucl Med. 2012;26:381-9.
23. Adams RR, Whitmore FC. Heterocyclic basic compounds. IV. 2-aminoalkylamino-pyrimidines1. J Am Chem Soc. 1945;67:735-8.
24. Narla RK, Liu XP, Myers DE, Uckun FM. 4-(3′-Bromo- 4′hydroxylphenyl)- amino-6, 7-dimethoxyquinazoline: a novel quinazoline derivative with potent cytotoxic activity against human glioblastoma cells. Clin Can Res. 1998;4:1405-14.
25. Van Brocklin HF, Lim JK, Coffing SL, Hom DL, Negash K, Ono MY, et al. Anilinodialkoxyquinazolines: screening epidermal growth factor receptor tyrosine kinase inhibitors for potential tumor imaging probes. J Med Chem. 2005;48:7445-56.
26. Rewcastle GW, Palmer BD, Bridges AJ, Showalter HDH, Sun L, Nelson J, et al. Tyrosine kinase inhibitors. 9. Synthesis and evaluation of fused tricyclic quinazoline analogues as ATP site inhibitors of the tyrosine kinase activity of the epidermal growth factor receptor. J Med Chem. 1996;39:918-28.
27. Morley JS, Simpson JCE. The chemistry of simple heterocyclic systems. Part III. Basic centres of 4-substituted quinazoline derivatives. J Chem Soc. 1949;286:1354-6.
28. Rewcastle GW, Denny WA, Bridges AJ, Zhou H, Cody DR, McMichael A, Fry DW. 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. 1995;38:3482-7.
29. Bridges AJ, Zhou H, Cody DR, Rewcastle GW, McMichael A, Showalter HDH, et al. Tyrosine kinase inhibitors. 8. An unusually steep structure-activity relationship for analogues of 4-(3-bromoanilino)-6, 7-dimethoxyquinazoline (PD153035), a potent Inhibitor of the epidermal growth factor receptor. J Med Chem. 1996;39:267-76.
30. Hennequin LF, Thomas AP, Johnstone C, Stokes ES, Ple PA, Lohmann JJ, et al. Design and structure-activity relationship of a new class of potent VEGF receptor tyrosine kinase inhibitors. J Med Chem. 1999;42:53-9.
31. Smaill J, Rewcastle GW, Loo JA, Greis KD, Chan OH, Reyner EL, Lipka E. Showalter HD, Vincent PW, Elliott WL, Denny WA. Tyrosine kinase inhibitors. 17. irreversible inhibitors of the epidermal growth factor receptor: 4-(phenylamino)quinazoline- and 4-(phenylamino)pyrido[3,2-d]pyrimidine-6- acrylamides bearing additional solubilizing functions. J Med Chem. 2000;43:1380-97.
32. Tsou HR, Mamuya N, Johnson BD, Reich MF, Gruber BC, Ye F, et al. 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. 2001;44:2719-34.
33. Rewcastle GW, Murray DK, Elliott WL, Fry DW, Howard CT, Nelson JM, et al. A tyrosine kinase inhibitors. 14. Structure-activity relationships for methyl- amino-substituted derivatives of 4-[(3-bromophenyl)amino]-6-(methylamino)- pyrido[3, 4-d]pyrimidine (PD 158780), a potent and specific inhibitor of the tyrosine kinase activity of receptors for the EGF family of growth factors. J Med Chem. 1998;41:742-51.
34. Yuan F, Chen Y, Dellian M, Safabakhsh N, Ferrara N, Jain RK. Time-dependent vascular regression and permeability changes in established human tumor xenografts induced by an anti-vascular endothelial growth factor/vascular permeability factor antibody. Proc Natl Acad Sci USA. 1996;93(25):14765-70.
35. Sane DC, Brosnihan KB. Angiogenic growth factors and hypertension. Angiogegesis. 2004;7(3):193-201.
36. Bridges AJ, Cody DR, Zhou H, McMichael A, Fry DW. Enantioselective inhibition of the epidermal growth factor receptor tyrosine kinase by 4-(phenethylamino)quinazolines. Bioorg Med Chem. 1995;3:1651-6.
37. Paez JG, Jänne PA, Lee JC, Tracy S, Greulich H, Gabriel S, et al. EGFR mutations in lung cancer: correlation with clinical response to gefitinib therapy. Science. 2004;304:1497-500.