Nuclear Medicine and Biology
Volume 36, Issue 5 , Pages 477-487 , July 2009

Radiosynthesis of [131I]IAZGP via nucleophilic substitution and its biological evaluation as a hypoxia marker — is specific activity a factor influencing hypoxia-mapping ability of a hypoxia marker?

  • Makiko Suehiro

      Affiliations

    • Department of Medical Physics, Memorial Sloan Kettering Cancer Center, New York, NY 10065, USA
    • Corresponding Author InformationCorresponding author. Tel.: +1 646 888 2153; fax: +1 212 639 2611.
    • ,
  • Paul Burgman

      Affiliations

    • Department of Medical Physics, Memorial Sloan Kettering Cancer Center, New York, NY 10065, USA
    • ,
  • Sean Carlin

      Affiliations

    • Department of Medical Physics, Memorial Sloan Kettering Cancer Center, New York, NY 10065, USA
    • ,
  • Sean Burke

      Affiliations

    • Department of Medical Physics, Memorial Sloan Kettering Cancer Center, New York, NY 10065, USA
    • ,
  • Guangbin Yang

      Affiliations

    • Organic Synthesis Core Facility, Memorial Sloan Kettering Cancer Center, New York, NY 10065, USA
    • ,
  • Ouathek Ouerfelli

      Affiliations

    • Organic Synthesis Core Facility, Memorial Sloan Kettering Cancer Center, New York, NY 10065, USA
    • ,
  • Christoph Oehler-Janne

      Affiliations

    • Department of Medical Physics, Memorial Sloan Kettering Cancer Center, New York, NY 10065, USA
    • ,
  • Joseph O'Donoghue

      Affiliations

    • Department of Medical Physics, Memorial Sloan Kettering Cancer Center, New York, NY 10065, USA
    • ,
  • Clifton Ling

      Affiliations

    • Department of Medical Physics, Memorial Sloan Kettering Cancer Center, New York, NY 10065, USA
    • ,
  • John Humm

      Affiliations

    • Department of Medical Physics, Memorial Sloan Kettering Cancer Center, New York, NY 10065, USA

Received 30 September 2008 ,Revised 24 February 2009 ,Accepted 6 March 2009.

References 

  1. Ling CC, Humm J, Larson S, Amols H, Fuks Z, Leibel S, et al. Toward multidimensional radiotherapy (MD-CRT): biological imaging and biological conformity. Int J Radiat Oncol Biol Phys. 2000;47:551–560
  2. Schinagl DAX, Kaanders JHAM, Oyen WJG. From anatomical to biological target volumes: the role of PET in radiation treatment planning. Cancer Imaging. 2006;6:S107–S116
  3. Thorwarth D, Eschmann SM, Paulsen F, Alber M. A model of reoxygenation dynamics of head-and-neck tumors based on serial 18F-fluoromisonidazole positron emission tomography investigations. Int J Radiation Oncology Biol Phys. 2007;68:515–521
  4. Rajendran JG, Hendrickson KRG, Spence AM, Krohn KA, Mankoff DA. Hypoxia imaging-directed radiation treatment planning. Eur J Nucl Med Mol Imaging. 2006;33:S44–S53
  5. Lecchi M, Fossati P, Elisei F, Orecchia R, Lucignani G. Current concepts on imaging in radiotherapy. Eur J Nucl Med Mol Imaging. 2008;53:821–837
  6. Lee NY, Mechalakos JG, Nehmeh S, Lin Z, Squire OD, Cai S, et al. Fluorine-18-labeled fluoromisonidazole positron emission and computed tomography-guided intensity-modulated radiotherapy for head and neck cancer: a feasible study. Int J Radiat Oncol Biol Phys. 2008;70:2–13
  7. Sorger D, Patt M, Kumar P, Wiebe LI, Barthel H, Seese A, et al. [18F]fluoroazomycinarabinoside (18FAZA) and [18F]fluoromisonidazole (18FMISO): a comparative study of their selective uptake in hypoxia cells and PET imaging in experimental rat tumors. Nucl Med Biol. 2003;30:317–326
  8. Zanzonico P, O’Donoghue J, Chapman JD, Schneider R, Cai S, Larson S, et al. 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
  9. Piert M, Machulla HJ, Picchio M, Reischl G, Ziegler S, Kumar P, et al. Hypoxia-specific tumor imaging with 18F-fluoroazomycin arabinoside. J Nucl Med. 2005;46:106–113
  10. Reischl G, Dorow DS, Cullinane C, Katsifis A, Roselt P, Binns D, et al. Imaging of tumor hypoxia with [124I]IAZA in comparison with [18F]FMISO, [18F]FAZA-First small animal PET results. J Pharm Pharmaceut Sci. 2007;10:172–180
  11. Mannan RH, Somayaji VV, Lee J, Mercer JR, Chapman JD, Wieber LI. Radioiodinated 1-(5-iodo-5-deoxy-b-D-arabinofuranosyl)-2-nitroimidazole, iodoazomycin arabinoside: IAZA): a novel marker of tissue hypoxia. J Nucl Med. 1991;32:1764–1770
  12. Mannan RH, Mercer JR, Wieber LI, Kumar P, Somayaji VV, Chapman JD. Radioiodinated azomycin pyranoside (IAZP): a new non-invasive marker for the assessment of tumor hypoxia. J Nucl Biol Med. 1992;36:60–67
  13. Parliament MB, Chapman JD, Urtasun RC, McEwan AJ, Goldberg L, Mercer JR, et al. Non-invasive assessment of human tumour hypoxia with 123I-iodoazomycin arabinoside: preliminary report of a clinical study. Br J Cancer. 1992;65:90–95
  14. Urtasun RC, Parliament MB, McEwan AJ, Mercer JR, Mannan RH, Wieber LI, et al. Measurement of hypoxia in human tumors by non-invasive SPECT imaging of iodoazomycin arabinoside. Br J Cancer. 1996;27:S209–S212
  15. Schneider RF, Engelhardt EL, Stobbe CC, Fenning MC, Chapman JD. The synthesis and radiolabeling of novel markers of tissue hypoxia of the iodinated azomycin nucleoside class. J Labelled Compd Radiopharm. 1997;39:541–557
  16. Varghese AJ, Whitmore GF. Binding of cellular macromolecules as a possible mechanism for the cytotoxicity of misonidazole. Cancer Res. 1980;40:2165–2169
  17. Miller GG, Ngan-Lee J, Chapman JD. Intracellular localization of radioactively labeled misonidazole in EMT-6 tumor cells in vitro. Int J Radiation Oncology. Biol Phys. 1982;8:741–744
  18. Chapman JD, Baer K, Lee J. Characteristics of the metabolism-induced binding of misonidazole to hypoxic mammalian cells. Cancer Res. 1983;43:1523–1528
  19. Chapman JD, Coia LR, Stobbe CC, Engelhardt EL, Fenning MC, Schneider RF. Prediction of tumor hypoxia and radioresistance with nuclear medicine markers. Br J Cancer. 1996;74:S204–S208
  20. Koch CJ, Stobbe CC, Baer KA. Metabolism induced binding of 14C-misonidazole to hypoxic cells: kinetic dependence on oxygen concentration and misonidazole concentration. Int J Radiation Oncology Biol Phys. 1983;10:1327–1331
  21. Kumar P, Wiebe LI, Asikoglu M, Tandon M, McEwan AJB. Microwave-assisted (radio)halogenation of nitroimidazole-based hypoxia markers. Appl Radiat Isot. 2002;57:697–703
  22. Burgman P, O'Donoughue JA, Lews JS, Welch MJ, Humm JL, Ling CC. Cell line-dependent differences in uptake and retention of the hypoxia-selective nuclear imaging agent Cu-ATSM. Nucl Med Biol. 2005;32:623–630
  23. Engelhardt EL, Schneider RF, Seeholzer SH, Stobbe CC, Chapman JD. The synthesis and radiolabeling of cyclam and their preclinical evaluation as positive markers of tumor hypoxia. J Nucl Med. 2002;43:837–850
  24. Pugachev A, Ruan S, Carlin Slarson SM, Campa J, Ling CC, Humm JL. Dependence of FDG uptake on tumor microenvironment. Int J Radiat Oncol Biol Phys. 2005;62:545–553
  25. Suehiro M, Vallabhajosula S, Goldsmith SJ, Ballon D. Investigation of the role of the base in the synthesis of [18F]FLT. Appl Radiat Isot. 2007;65:1350–1357
  26. Iyer RV, Haynes PT, Schneider RF, Movsas B, Chapman JD. -d-[βMarking hypoxia in rat prostate carcinomas with [125I]azomycin galactopyranoside and [99mTc]HL-91: correlation with microelectrode measurements. J Nucl Med. 2001;42:337–344
  27. Moore RB, Chapman JD, Mercer JR, Mannan RH, Wiebe LI, McEwan AJ, et al. Measurement of PDT-induced hypoxia in Dunning prostate tumors by iodine-123-iodoazomycin arabinoside. J Nucl Med. 1993;34:405–413
  28. Nuclide safety data sheet . Radiation protection dosimetry-radionuclide and radiation protection data handbook. In:  Delacriox D editors. Kent, England: Nuclear Technology Publishing; 1998;
  29. Prekeges JL, Rasey JS, Grunbaum Z, Krohn KH. Reduction of fluoromisonidazole, a new imaging agent for hypoxia. Biochem Pharmacol. 1991;42:2387–2395
  30. Rasey JS, Grunbaum Z, Magee S, Nelson NJ, Olive PL, Durand RE, et al. Characterization of radiolabeled fluoromisonidazole as a probe for hypoxic cells. Radiat Res. 1987;111:292–304
  31. Wyss MT, Honer M, Schubiger PA, Ametamey SM. NanoPET imaging of [18F]fluoromisonidazole uptake in experimental mouse tumors. Eur J Nucl Med Mol Imaging. 2006;33:311–318
  32. Hirst DG, Hazelhurst DG, Brown JM. Changes in misonidazole binding with hypoxic fraction in mouse tumors. Int J Radiat Oncol Biol Phys. 1985;11:1349–1355
  33. Garrecht BM, Chapman JD. The labeling of EMT-6 tumours in BALB/C mice with 14C-misonidazole. Br J Radiol. 1983;56:745–753
  34. Parliament MB, Wiebe LI, Franko AJ. Nitroimidazole adducts as markers for tissue hypoxia: mechanistic studies in aerobic normal tissues and tumour cells. Br J Cancer. 1992;66:1103–1110
  35. Procissi D, Claus F, Burgman P, Koziorowski J, Chapman JD, Thakur SB, et al. In vivo 19F magnetic resonance spectroscopy and chemical shift if tri-fluoro-nitroimidaziole as a potential hypoxia reporter in solid tumors. Clin Cancer Res. 2007;13:3738–3747
  36. Suehiro M, Scheffel U, Dannals RF, Ricaurte GA, Ravert HT, Wagner HN. A PET radiotracer for studying serotonin uptake sites; [11C]McN-5652-Z. J Nucl Med. 1993;34:120–127

PII: S0969-8051(09)00078-X

doi: 10.1016/j.nucmedbio.2009.03.002

Nuclear Medicine and Biology
Volume 36, Issue 5 , Pages 477-487 , July 2009

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