A simplified synthesis of the hypoxia imaging agent 2-(2-Nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-[18F]pentafluoropropyl)-acetamide ([18F]EF5)

Nuclear Medicine and Biology

Volumn 39, Issue 7, 2012, Pages 1012-1018

  Chitneni, Satish K ^a   Bida, Gerald T ^a   Dewhirst, Mark W ^a   Zalutsky, Michael R ^a  

^a DUKE UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

18F EF5; Hypoxia; Oasis cartridge; On line SPE; PET

Indexed keywords

2 (2 NITRO 1H IMIDAZOL 1 YL) N (2,2,3,3,3 PENTAFLUOROPROPYL)ACETAMIDE; 2 (2 NITRO 1H IMIDAZOL 1 YL) N (2,2,3,3,3 PENTAFLUOROPROPYL)ACETAMIDE F 18; DEUTERIUM; NICKEL; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; AUTOMATION; COLORECTAL CANCER; CONTROLLED STUDY; CYCLOTRON; DRUG MUSCLE LEVEL; DRUG PURIFICATION; DRUG RETENTION; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TUMOR LEVEL; ELUTION; EVAPORATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; ISOTOPE LABELING; MALE; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RADIOACTIVITY; SEPARATION TECHNIQUE; SOLID PHASE EXTRACTION; TUMOR VOLUME; TUMOR XENOGRAFT;

ANIMALS; CELL HYPOXIA; CHEMISTRY TECHNIQUES, SYNTHETIC; COLORECTAL NEOPLASMS; CYCLOTRONS; ETANIDAZOLE; FEMALE; HCT116 CELLS; HUMANS; HYDROCARBONS, FLUORINATED; MICE; MICE, NUDE; POSITRON-EMISSION TOMOGRAPHY; RADIOCHEMISTRY; SOLID PHASE EXTRACTION;

EID: 84866035479     PISSN: 09698051     EISSN: 18729614     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2012.05.006     Document Type: Article

References (47)

1. 2 histography. Antioxid Redox Signal 2007, 9:1221-1235.
2. Brizel D.M., Sibley G.S., Prosnitz L.R., Scher R.L., Dewhirst M.W. Tumor hypoxia adversely affects the prognosis of carcinoma of the head and neck. Int J Radiat Oncol Biol Phys 1997, 38:285-289.
3. Semenza G.L. Hypoxia, clonal selection, and the role of HIF-1 in tumor progression. Crit Rev Biochem Mol Biol 2000, 35:71-103.
4. Harris A.L. Hypoxia - a key regulatory factor in tumour growth. Nat Rev Cancer 2002, 2:38-47.
5. Pennacchietti S., Michieli P., Galluzzo M., Mazzone M., Giordano S., Comoglio P.M. Hypoxia promotes invasive growth by transcriptional activation of the met protooncogene. Cancer Cell 2003, 3:347-361.
6. Papandreou I., Cairns R.A., Fontana L., Lim A.L., Denko N.C. HIF-1 mediates adaptation to hypoxia by actively downregulating mitochondrial oxygen consumption. Cell Metab 2006, 3:187-197.
7. Gort E.H., Groot A.J., van der Wall E., van Diest P.J., Vooijs M.A. Hypoxic regulation of metastasis via hypoxia-inducible factors. Curr Mol Med 2008, 8:60-67.
8. Rofstad E.K., Sundfor K., Lyng H., Trope C.G. Hypoxia-induced treatment failure in advanced squamous cell carcinoma of the uterine cervix is primarily due to hypoxia-induced radiation resistance rather than hypoxia-induced metastasis. Br J Cancer 2000, 83:354-359.
9. Tredan O., Galmarini C.M., Patel K., Tannock I.F. Drug resistance and the solid tumor microenvironment. J Natl Cancer Inst 2007, 99:1441-1454.
10. Shannon A.M., Bouchier-Hayes D.J., Condron C.M., Toomey D. Tumour hypoxia, chemotherapeutic resistance and hypoxia-related therapies. Cancer Treat Rev 2003, 29:297-307.
11. Graeber T.G., Osmanian C., Jacks T., Housman D.E., Koch C.J., Lowe S.W., et al. Hypoxia- mediated selection of cells with diminished apoptotic potential in solid tumours. Nature 1996, 379:88-91.
12. Gottesman M.M., Fojo T., Bates S.E. Multidrug resistance in cancer: role of ATP-dependent transporters. Nat Rev Cancer 2002, 2:48-58.
13. Vordermark D., Brown J.M. Endogenous markers of tumor hypoxia - predictors of clinical radiation resistance? Strahlentherapie Und. Onkologie 2003, 179:801-811.
14. Ljungkvist A.S.E., Bussink J., Kaanders J., Van der Kogel A.J. Dynamics of tumor hypoxia measured with bioreductive hypoxic cell markers. Radiat Res 2007, 167:127-145.
15. Krohn K.A., Link J.M., Mason R.P. Molecular imaging of hypoxia. J Nucl Med 2008, 49:129S-148S.
16. Bussink J., Kaanders J., van der Kogel A.J. Tumor hypoxia at the micro-regional level: clinical relevance and predictive value of exogenous and endogenous hypoxic cell markers. RadiotherOncol 2003, 67:3-15.
17. 18F-fluoromisonidazole. Semin Nucl Med 2007, 37:451-461.
18. 18F-FAZA). Eur J Nucl Med Mol Imaging 2009, 36:1565-1573.
19. 18F-EF5: a new PET tracer for imaging hypoxia in head and neck cancer. J Nucl Med 2008, 49:1944-1951.
20. 60Cu-ATSM: relationship to therapeutic response - a preliminary report. Int J Radiat Oncol Biol Phys 2003, 55:1233-1238.
21. Nunn A., Linder K., Strauss H.W. Nitroimidazoles and imaging hypoxia. Eur J Nucl Med Mol 1995, 22:265-280.
22. Kaanders J.H., Wijffels K.I., Marres H.A., Ljungkvist A.S., Pop L.A., van den Hoogen F.J., et al. Pimonidazole binding and tumor vascularity predict for treatment outcome in head and neck cancer. Cancer Res 2002, 62:7066-7074.
23. Evans S.M., Fraker D., Hahn S.M., Gleason K., Jenkins W.T., Jenkins K., et al. EF5 binding and clinical outcome in human soft tissue sarcomas. Int J Radiat Oncol Biol Phys 2006, 64:922-927.
24. Evans S.M., Judy K.D., Dunphy I., Jenkins W.T., Hwang W.T., Nelson P.T., et al. Hypoxia is important in the biology and aggression of human glial brain tumors. Clin Cancer Res 2004, 10:8177-8184.
25. 18F-EF5, a marker for PET detection of hypoxia: synthesis of precursor and a new fluorination procedure. Appl Radiat Isotopes 2001, 54:73-80.
26. 18F-EF5. Eur J Nucl Med Mol 2003, 30:259-266.
27. 18F-EF5 uptake. Int J Radiat Oncol Biol Phys 2009, 85:1137-1147.
28. 18F-EF5 uptake versus EF5 binding in human glioblastoma. Eur J Nucl Med Mol 2010, 37:2048-2059.
29. Koch C.J., Hahn S.M., Rockwell K., Covey J.M., McKenna W.G., Evans S.M. Pharmacokinetics of EF5 2-(2-nitro-1-H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl) acetamide in human patients: implications for hypoxia measurements in vivo by 2-nitrolmidazoles. Cancer Chemother Pharmacol 2001, 48:177-187.
30. 2. Nucl Med Biol 1996, 23:181-188.
31. 18F]EF5. Mol Imaging Biol 2011.
32. 18F PET agents. Appl Radiat Isotopes 2010, 68:293-296.
33. 18F]EF5). J Nucl Med 2011, 52(Supp 1):1428.
34. Knoess C., Siegel S., Smith A., Newport D., Richerzhagen N., Winkeler A., et al. Performance evaluation of the microPET R4 PET scanner for rodents. Eur J Nucl Med Mol Imaging 2003, 30:737-747.
35. Charged particle cross-section database for medical radioisotope production: Diagnostic radioisotopes and monitor reactions. IAEA-TECDOC-1211, Vienna 2001; see also updated information at www-nds.iaea.org/medical/.
36. Wieland B.W., Fowler J.S., Wolf A.P. Multi-purpose target unit for small cyclotrons. J Label Cmpds Radiopharm 1984, 21:1250-1251.
37. 2. Proc. of the Vth International Workshop on Targetry and Target Chemistry 1994, 219. Brookhaven National Laboratory, Upton, New York. J.R. Dahl, R. Ferrieri, R. Finn, D.J. Schlyer (Eds.).
38. El-Wakil M.M. Nuclear heat transport 1971, International Textbook Co., Scranton (Pa).
39. 18F-EF5. J Label Compd Radiopharm 2011, 54:S408.
40. 18F]FAZA PET in head and neck cancer patients: a pilot study. Eur J Nucl Med Mol Imaging 2007, 34:1566-1575.
41. Wang J., Foehrenbacher A., Su J., Patel R., Hay M.P., Hicks K., et al. The 2-nitroimidazole EF5 is a biomarker for oxidoreductases that activate the bioreductive prodrug CEN-209 under hypoxia. Clin Cancer Res 2011, 1684-1695.
42. Evans S.M., Joiner B., Jenkins W.T., Laughlin K.M., Lord E.M., Koch C.J. Identification of hypoxia in cells and tissues of epigastric 9L rat glioma using EF5 [2-(2-nitro-lH-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl) acetamide]. Br J Cancer 1995, 72:875-882.
43. Cao Y., Li C.Y., Moeller B.J., Yu D., Zhao Y., Dreher M.R., et al. Observation of incipient tumor angiogenesis that is independent of hypoxia and hypoxia inducible factor-1 activation. Cancer Res 2005, 65:5498-5505.
44. Cao Y., Sonveaux P., Liu S., Zhao Y., Mi J., Clary B.M., et al. Systemic overexpression of angiopoietin-2 promotes tumor microvessel regression and inhibits angiogenesis and tumor growth. Cancer Res 2007, 67:3835-3844.
45. 18F-fluoroazomycin arabinoside. J Nucl Med 2005, 46:106-113.
46. 18F]FAZA-first small animal PET results. J Pharm Pharm Sci 2007, 10:203-211.
47. 18FMISO): a comparative study of their selective uptake in hypoxic cells and PET imaging in experimental rat tumors. Nucl Med Biol 2003, 30:317-326.