Radiosynthesis and initial in vitro evaluation of [ 18F]F- PEG 6-IPQA-A novel PET radiotracer for imaging EGFR expression-activity in lung carcinomas

Molecular Imaging and Biology

Volumn 13, Issue 5, 2011, Pages 853-861

  Pal, Ashutosh ^a   Balatoni, Julius A ^a   Mukhopadhyay, Uday ^a   Ogawa, Kazuma ^b   Gonzalez Lepera, Carlos ^a   Shavrin, Aleksandr ^a   Volgin, Andrei ^a   Tong, William ^a   Alauddin, Mian M ^a   Gelovani, Juri G ^a  

^a UNIVERSITY OF TEXAS MD ANDERSON CANCER CENTER   (United States)

^b KANAZAWA UNIVERSITY   (Japan)

Author keywords

18F F PEG 6 IPQA; Epidermal growth factor receptor; Non small cell lung carcinoma; Positron emission tomography; Radiochemistry

Indexed keywords

4 [(3 IODOPHENYL)AMINO] 7 [2 [2 [2 [2 [2 [2 (FLUOROETHOXY)] ETHOXY]ETHOXY]ETHOXY]ETHOXY]ETHOXY]QUINAZOLINE 6 YL ACRYLAMIDE F 18; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG; VASCULOTROPIN RECEPTOR;

ARTICLE; BIOACCUMULATION; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IMAGE ANALYSIS; IN VITRO STUDY; LUNG NON SMALL CELL CANCER; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN PHOSPHORYLATION; RADIOCHEMISTRY;

CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLUORINE RADIOISOTOPES; HUMANS; LUNG NEOPLASMS; POSITRON-EMISSION TOMOGRAPHY; QUINAZOLINES; RECEPTOR, EPIDERMAL GROWTH FACTOR; SMALL CELL LUNG CARCINOMA;

EID: 84855700865     PISSN: 15361632     EISSN: 18602002     Source Type: Journal    
DOI: 10.1007/s11307-010-0408-8     Document Type: Article

References (23)

1. ACS (2009) Cancer Reference Information. http://wwwcancerorg/docroot/ CRI/content/CRI-2-4-1x-What-Are-the-Key-Statistics-About-Lung-Cancer-15asp? sitearea=
2. Mishani E, Abourbeh G (2007) Cancer molecular imaging: Radionuclide- based biomarkers of the epidermal growth factor receptor (EGFR). Curr Top Med Chem 7:1755-1772 (Pubitemid 350130995)
3. Mishani E, Hagooly A (2009) Strategies for molecular imaging of epidermal growth factor receptor tyrosine kinase in cancer. J Nucl Med 50:1199-1202
4. Bonasera TA, Ortu G, Rozen Y, Krais R, Freedman NM, Chisin R, Gazit A, Levitzki A, Mishani E (2001) Potential (18)F-labeled biomarkers for epidermal growth factor receptor tyrosine kinase. Nucl Med Biol 28:359-374 (Pubitemid 32520994)
5. Ortu G, Ben-David I, Rozen Y, Freedman NM, Chisin R, Levitzki A, Mishani E (2002) 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 101:360-370 (Pubitemid 34983192)
6. Mishani E, Abourbeh G, Rozen Y, Jacobson O, Laky D, Ben David I, Levitzki A, Shaul M (2004) Novel carbon-11 labeled 4-dimethylaminobut- 2-enoic acid [4-(phenylamino)-quinazoline-6-yl]-amides: Potential PET bioprobes for molecular imaging of EGFR-positive tumors. Nucl Med Biol 31:469-476 (Pubitemid 38490746)
7. Abourbeh G, Dissoki S, Jacobson O, Litchi A, Ben Daniel R, Laki D, Levitzki A, Mishani E (2007) 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 34:55-70 (Pubitemid 46038157)
8. Dissoki S, Aviv Y, Laky D, Abourbeh G, Levitzki A, Mishani E (2007) The effect of the [18F]-PEG group on tracer qualification of [4- (phenylamino)-quinazoline-6-YL]-amide moiety-an EGFR putative irreversible inhibitor. Appl Radiat Isot 65:1140-1151 (Pubitemid 47333371)
9. Pal A, Glekas A, Doubrovin M, Balatoni J, Namavari M, Beresten T, Maxwell D, Soghomonyan S, Shavrin A, Ageyeva L, Finn R, Larson SM, Bornmann W, Gelovani JG (2006) Molecular imaging of EGFR kinase activity in tumors with 124I-labeled small molecular tracer and positron emission tomography. Mol Imaging Biol 8:262-277 (Pubitemid 44446020)
10. Su H, Seimbille Y, Ferl GZ, Bodenstein C, Fueger B, Kim KJ, Hsu YT, Dubinett SM, Phelps ME, Czernin J, Weber WA (2008) Evaluation of [(18)F]gefitinib as a molecular imaging probe for the assessment of the epidermal growth factor receptor status in malignant tumors. Eur J Nucl Med Mol Imaging 35:1089-1099
11. Wang H, Yu JM, Yang GR, Song XR, Sun XR, Zhao SQ, Wang XW, Zhao W (2007) Further characterization of the epidermal growth factor receptor ligand 11C-PD153035. Chin Med J (Engl) 120:960-964 (Pubitemid 46902174)
12. Memon AA, Jakobsen S, Dagnaes-Hansen F, Sorensen BS, Keiding S, Nexo E (2009) Positron emission tomography (PET) imaging with [11C]-labeled erlotinib: A micro-PET study on mice with lung tumor xenografts. Cancer Res 69:873-878
13. Pantaleo MA, Mishani E, Nanni C, Landuzzi L, Boschi S, Nicoletti G, Dissoki S, Paterini P, Piccaluga PP, Lodi F, Lollini PL, Fanti S, Biasco G. (2010) Evaluation of modified PEG-anilinoquinazoline derivatives as potential agents for EGFR imaging in cancer by small animal PET. Mol Imaging Biol. doi:10.1007/s11307-010-0315-z
14. Liu N, Li M, Li X, Meng X, Yang G, Zhao S, Yang Y, Ma L, Fu Z, Yu J (2009) PET-based biodistribution and radiation dosimetry of epidermal growth factor receptor-selective tracer 11C-PD153035 in humans. J Nucl Med 50:303-308
15. Gelovani JG (2008) Molecular imaging of epidermal growth factor receptor expression-activity at the kinase level in tumors with positron emission tomography. Cancer Metastasis Rev 27:645-653
16. Paez JG, Janne PA, Lee JC, Tracy S, Greulich H, Gabriel S, Herman P, Kaye FJ, Lindeman N, Boggon TJ, Naoki K, Sasaki H, Fujii Y, Eck MJ, Sellers WR, Johnson BE, Meyerson M (2004) EGFR mutations in lung cancer: Correlation with clinical response to gefitinib therapy. Science (New York, NY) 304:1497-1500 (Pubitemid 38720929)
17. Mukohara T, Engelman JA, Hanna NH, Yeap BY, Kobayashi S, Lindeman N, Halmos B, Pearlberg J, Tsuchihashi Z, Cantley LC, Tenen DG, Johnson BE, Janne PA (2005) Differential effects of gefitinib and cetuximab on non-small-cell lung cancers bearing epidermal growth factor receptor mutations. J Natl Cancer Inst 97:1185-1194 (Pubitemid 41258224)
18. Tracy S, Mukohara T, Hansen M, Meyerson M, Johnson BE, Janne PA (2004) Gefitinib induces apoptosis in the EGFRL858R non-small-cell lung cancer cell line H3255. Cancer Res 64:7241-7244 (Pubitemid 39372059)
19. Najjar AM, Nishii R, Maxwell DS, Volgin A, Mukhopadhyay U, Bornmann WG, Tong W, Alauddin M, Gelovani JG (2009) Moleculargenetic PET imaging using an HSV1-tk mutant reporter gene with enhanced specificity to acycloguanosine nucleoside analogs. J Nucl Med 50:409-416
20. Wissner A, Fraser HL, Ingalls CL, Dushin RG, Floyd MB, Cheung K, Nittoli T, Ravi MR, Tan X, Loganzo F (2007) Dual irreversible kinase inhibitors: Quinazoline-based inhibitors incorporating two independent reactive centers with each targeting different cysteine residues in the kinase domains of EGFR and VEGFR-2. Bioorg Med Chem 15:3635-3648 (Pubitemid 46635150)
21. MacMahon S, Fong R 2nd, Baran PS, Safonov I, Wilson SR, Schuster DI (2001) Synthetic approaches to a variety of covalently linked porphyrin-fullerene hybrids. J Org Chem 66:5449-5455 (Pubitemid 32878898)
22. Dissoki S, Eshet R, Billauer H, Mishani E (2009) Modified PEGanilinoquinazoline derivatives as potential EGFR PET agents. J Label Comp Radiopharm 52:41-52
23. Iino T, Sasaki Y, Bamba M, Mitsuya M, Ohno A, Kamata K, Hosaka H, Maruki H, Futamura M, Yoshimoto R, Ohyama S, Sasaki K, Chiba M, Ohtake N, Nagata Y, Eiki J, Nishimura T (2009) Discovery and structure-activity relationships of a novel class of quinazoline glucokinase activators. Bioorganic & Medicinal Chemistry Letters 19 (19):5531-5538