Preclinical validation of the hypoxia tracer 2-(2-nitroimidazol-1-yl)-N-(3, 3,3-[18F]trifluoropropyl)acetamide, [18F]EF3

European Journal of Nuclear Medicine and Molecular Imaging

Volumn 31, Issue 9, 2004, Pages 1263-1272

  Mahy, P ^a   De Bast, M ^a   Leveque, P H ^b   Gillart, J ^b   Labar, D ^b   Marchand, J ^b   Gregoire, V ^a  

^a CLINIQUES UNIVERSITAIRES SAINT LUC   (Belgium)

^b UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Drug evaluation, preclinical; Hypoxia; Nitroimidazoles; PET; Pharmacokinetics

Indexed keywords

2 (NITROIMIDAZOL 1 YL) N (3,3,3 TRIFLUOROPROPYL)ACETAMIDE F 18; DRUG METABOLITE; TRACER; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG BLOOD LEVEL; DRUG DISTRIBUTION; DRUG FECES LEVEL; DRUG HALF LIFE; DRUG METABOLISM; DRUG SCREENING; DRUG SYNTHESIS; DRUG TISSUE LEVEL; DRUG URINE LEVEL; EX VIVO STUDY; GASTROINTESTINAL TRACT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYPOXIC CELL; KIDNEY METABOLISM; LIVER METABOLISM; MALE; MOUSE; NONHUMAN; OXYGENATION; RADIOACTIVITY; URINARY TRACT; VALIDATION PROCESS;

ANIMALS; CARCINOMA; CELL HYPOXIA; CELL LINE, TUMOR; DRUG EVALUATION, PRECLINICAL; FIBROSARCOMA; MALE; METABOLIC CLEARANCE RATE; MICE; MICE, INBRED C3H; NITROIMIDAZOLES; ORGAN SPECIFICITY; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; TISSUE DISTRIBUTION;

EID: 4544242405     PISSN: 16197070     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00259-004-1573-2     Document Type: Article

References (47)

1. Horsman MR, Nordsmark M, Overgaard J. Techniques to assess the oxygenation of human tumors. State of the art. Strahlenther Onkol 1998;174(Suppl 4):2-5
2. Kennedy AS, Raleigh JA, Perez GM, et al. Proliferation and hypoxia in human squamous cell carcinoma of the cervix: first report of combined immunohistochemical assays. Int J Radiat Oncol Biol Phys 1997;37:897-905
3. Hodgkiss RJ. Use of 2-nitroimidazoles as bioreductive markers for tumour hypoxia. Anticancer Drug Des 1998;13:687-702
4. Busch TM, Hahn SM, Evans SM, Koch CJ. Depletion of tumor oxygenation during photodynamic therapy: detection by the hypoxia marker EF3 [2-(2-nitroimidazole-1[H]-yl)-N-(3,3,3-trifluoropropyl)acetamide]. Cancer Res 2000;60:2636-2642
5. Koch CJ. Measurement of absolute oxygen levels in cells and tissues using oxygen sensors and 2-nitroimidazole EF5. Methods Enzymol 2002;352:3-31
6. Raleigh JA, Koch CJ. The importance of thiols in the reductive binding of 2-nitroimidazoles to macromolecules. Biochem Pharmacol 1990;40:2457-2464
7. Kaanders JHAM, Wijffels KIEM, Marres HAM, Pop LAM, Marres HAM, Ljungkvist ASE, Pop LAM, van den Hoogen FJA, de Wilde PCM, Bussink J, Raleigh JA, van der Kogel AJ. Pimonidazole binding and tumor vascularity predict for treatment outcome in head and neck cancer. Cancer Res 2002;62:7066-7074
8. Evans SM, Judy KD, Dunphy I, Nelson P, Magarelli D, Jenkins WT, Hahn SM, Collins RM, Koch CJ. Hypoxia, as measured by EF5 binding, predicts recurrence in adult brain tumors. Int J Radiat Oncol Biol Phys 2003;55:470
9. Tubis M, Krishnamurthy G, Endow JS, Stein RA, Suwanik R, Blahd WH. Labeled metronidazole as potential agents for amebic abscess imaging. J Nucl Med 1975;14:163-171
10. Chapman JD, Franko AJ, Koch CJ. The fraction of hypoxic clonogenic cells in tumor populations. In: Nervi C, Arcangeli G, Mauro F, eds. Proceedings of the Second Rome International Symposium (1980): biological bases and clinical implications of tumor radioresistance. New York: Masson; 1983:61-73
11. Ballinger JR. Imaging hypoxia in tumors. Semin Nucl Med 2001;31:321-329
12. Rasey JS, Grunbaum Z, Magee S, et al. Characterization of radiolabeled fluoromisonidazole as a probe for hypoxic cells. Radiat Res 1987;111:292-304
13. Rasey JS, Koh WJ, Grierson JR, Grunbaum Z, Krohn KA. Radiolabeled fluoromisonidazole as an imaging agent for tumor hypoxia. Int J Radiat Oncol Biol Phys 1989;17:985-991
14. Rasey JS, Casciari JJ, Hofstrand PD, Muzi M, Graham MM, Chin LK. Determining hypoxic fraction in a rat glioma by uptake of radiolabeled fluoromisonidazole. Radiat Res 2000; 153:84-92
15. Koh WJ, Rasey JS, Evans ML, Grierson JR, Lewellen TK, Graham MM, Krohn KA, Griffin TW. Imaging of hypoxia in human tumors with [F-18] fluoromisonidazole. Int J Radiat Oncol Biol Phys 1992;22:199-212
16. Valk PE, Mathis CA, Prados MD, Gilbert JC, Budinger TF. Hypoxia in human gliomas: demonstration by PET with fluorine-18-fluoromisonidazole. J Nucl Med 1992;33:2133-2137
17. Koh WJ, Bergman KS, Rasey JS, et al. Evaluation of oxygenation status during fractionated radiotherapy in human nonsmall cell lung cancers using [F-18]fluoromisonidazole positron emission tomography. Int J Radiat Oncol Biol Phys 1995;33:391-398
18. 18F]fluoromisonidazole: a pretherapy study of 37 patients. Int J Radiat Oncol Biol Phys 1996;36:417-428
19. Yeh SH, Liu RS, Wu LC, Yang DJ, Yen SH, Chang CW, Yu TW, Chou KL, Chen KY. Fluorine-18 fluoromisonidazole tumour to muscle retention ratio for the detection of hypoxia in nasopharyngeal carcinoma. Eur J Nucl Med 1996; 23:1378-1383
20. Shelton ME, Dence CS, Hwang DR, Herrero P, Welch MJ, Bergmann SR. In vivo delineation of myocardial hypoxia during coronary occlusion using fluorine-18 fluoromisonidazole and positron emission tomography: a potential approach for identification of jeopardized myocardium. J Am Coll Cardiol 1990;16:477-485
21. 18F-fluoromisonidazole. Neurology 1998;51:1617-1621
22. Liu RS, Chu LS, Yen SH, Chang CP, Chou KL, Wu LC, Chang CW, Lui MT, Chen KY, Yeh SH. Detection of anaerobic odontogenic infections by fluorine-18 fluoromisonidazole. Eur J Nucl Med 1996;23:1384-1387
23. 18F]fluoroetanidazole: a potential new tracer for imaging hypoxia. Nucl Med Biol 1997;24:755-760
24. Yang DJ, Wallace S, Cherif A, Li C, Gretzer MB, Kim EE, Podoloff DA. Development of F-18-labeled fluoroerythronitroimidazole as a PET agent for imaging tumor hypoxia. Radiology 1995;194:795-800
25. 18F]fluoroerythronitroimidazole PET. J Nucl Med 2001;42:1643-1652
26. 18F]FETNIM) and PET using the tumour to plasma ratio. Eur J Nucl Med Mol Imaging 2003;30:101-108
27. Dewhirst MW. Concepts of oxygen transport at the microcirculatory level. Semin Radiat Oncol 1998;8:143-150
28. 18F-EF5. Eur J Nucl Med Mol Imaging 2003; 30:259-266
29. 18F]EF1. J Nucl Med 2000;41:327-336
30. 18F]-labelled EF3 [2-(2-nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl) -acetamide], a marker for PET detection of hypoxia. Bioorg Med Chem 2001;9:665-675
31. Milas L, Hunter N, Mason K, Withers HR. Immunological resistance to pulmonary metastases in C3Hf/Bu mice bearing syngeneic fibrosarcoma of different sizes. Cancer Res 1974; 34:61-71
32. Mahy P, De Bast M, Gallez B, Gueulette J, Koch CJ, Scalliet P, Grégoire V. In vivo colocalisation of 2-nitroimidazole EF5 fluorescence intensity and electron paramagnetic resonance oximetry in mouse tumors. Radiother Oncol 2003;67:53-61
33. 18F]FETNIM: a potential marker for PET. J Nucl Med 2001;42:1397-1404
34. Evans SM, Jenkins WT, Joiner B, Lord EM, Koch CJ. 2-Nitroimidazole (EF5) binding predicts radiation resistance in individual 9L s.c. tumors. Cancer Res 1996;56:405-411
35. Cobb LM, Nolan J, Butler SA. Distribution of pimonidazole and RSU 1069 in tumour and normal tissues. Br J Cancer 1990;62:915-918
36. Laughlin KM, Evans SM, Jenkins WT, et al. Biodistribution of the nitroimidazole EF5 (2-[2-nitro-1H-imidazol-1-yl]-N-(2,2,3,3,3-pentafluoropropyl) acetamide) in mice bearing subcutaneous EMT6 tumors. J Pharmacol Exp Ther 1996; 277:1049-1057
37. Phillips TL, Ross G. Time-dose relationships in the mouse esophagus. Radiology 1974;113:435-440
38. 3H-labelled misonidazole in the tumor-bearing mouse. Int J Radiat Oncol Biol Phys 1990;18:347-351
39. Cobb LM, Nolan J, Hacker T. Retention of misonidazole in normal and malignant tissues: interplay of hypoxia and reductases. Int J Radiat Oncol Biol Phys 1992;22:655-659
40. 18F-fluoride measured with positron emission tomography in correlation with CT. Skeletal Radiol 1998;27:72-76
41. 2 measurement in mice: effect of tumor site, site of implantation, and anesthesia. Rad Oncol Invest 1996;7:108-114
42. Mahy P, Gueulette J, Scalliet P, Grégoire V. Quantitative detection of EF5 adducts with immunofluorescence (IF) and flow cytometry (FC) to measure hypoxia in murine tumors. Cancer Res 1999;40:641
43. Chapman JD, Engelhardt EL, Stobbe CC, Schneider RF, Hanks GE. Measuring hypoxia and predicting tumor radio-resistance with nuclear medicine assays. Radiother Oncol 1998;46:229-237
44. Zanzonico P, O'Donoghue J, Chapman JD, Schneider R, Cai S, Larson S, Wen B, Chen Y, Finn R, Ruan S, Gerweck L, Humm J, Ling C. Iodine-124-labeled iodo-azomycin-galactoside imaging of tumor hypoxia in mice with serial microPET scanning. Eur J Nucl Med Mol Imaging 2004;31:117-128
45. 18F]fluoroetanidazole, a new radiopharmaceutical for detecting tumor hypoxia. J Nucl Med 1999;40:1072-1079
46. Graham MM, Peterson LM, Link JM, Evans ML, Rasey JS, Koh WJ, Caldwell JH, Krohn KA. Fluorine-18-fluoromisonidazole radiation dosimetry in imaging studies. J Nucl Med 1997;38:1631-1636
47. Koch CJ, Hahn SM, Rockwell Jr K, Covey JM, McKenna WG, Evans SM. Pharmacokinetics of EF5 [2-(2-nitro-1-H-imidazol-1-yl)-W-(2,2,3,3,3- pentafluoropropyl) acetamide] in human patients: implications for hypoxia measurements in vivo by 2-nitroimidazoles. Cancer Chemother Pharmacol 2001;48:177-187