Nuclear Medicine and Biology
Volume 37, Issue 2 , Pages 117-123 , February 2010

Preliminary studies of 99mTc-BnAO and its analogues: synthesis, radiolabeling and in vitro cell uptake

Received 10 July 2009 ,Revised 19 September 2009 ,Accepted 28 September 2009.

References 

  1. Brown JM, Giaccia AJ. Tumour hypoxia: the picture has changed in the 1990s. Int J Radiat Biol. 1994;65:95–102
  2. Gray LH, Conger AD, Ebert M, Hornsey S, Scott OCA. The concentration of oxygen dissolved in tissues at the time of irradiation as a factor in radiotherapy. Br J Radiol. 1953;26:638–648
  3. Janssen HL, Haustermans KM, Balm AJ, Begg AC. Hypoxia in head and neck cancer: how much, how important?. Head Neck. 2005;27:622–638
  4. Rasey JS, Koh WJ, Evans ML, Peterson LM, Lewellen TK, Graham MM, et al. Quantifying regional hypoxia in human tumors with positron emission tomography of [18F]fluoromisonidazole: a pretherapy study of 37 patients. Int J Radiat Oncol Biol Phys. 1996;36:417–428
  5. Bolla M, Gonzalez D, Warde P, Dubois JB, Mirimanoff RO, Storme G, et al. Improved survival in patients with locally advanced prostate cancer treated with radiotherapy and goserelin. N Engl J Med. 1997;337:295–300
  6. Abrantes AM, Serra ME, Murtinho D, Gonsalves AR, Botelho MF. An insight into tumoral hypoxia: the radiomarkers and clinical applications. Oncol Rev. 2009;3:3
  7. Fass L. Imaging and cancer: a review. Mol Oncol. 2008;2:115–152
  8. Hansell C. Nuclear medicine's double hazard. Nonprolif Rev. 2008;15:185–208
  9. Eckelman WC. Unparalleled contribution of technetium-99m to medicine over 5 decades. JACC Cardiovasc Imaging. 2009;2:364–368
  10. Horiuchi K, Tsukamoto T, Saito M, Nakayama M, Fujibayashi Y, Saji H. The development of 99mTc-analog of Cu-DTS as an agent for imaging hypoxia. Nucl Med Biol. 2000;27:391–399
  11. Cook GJ, Houston S, Barrington SF, Fogelman I. Technetium-99m-labeled HL91 to identify tumor hypoxia: correlation with fluorine-18-FDG. J Nucl Med. 1998;39:99–103
  12. Okada RD, Johnson G, Nguyen KN, Edwards B, Archer CM, Kelly JD. 99mTc-HL91. Effects of low flow and hypoxia on a new ischemia-avid myocardial imaging agent. Circulation. 1997;95:1892–1899
  13. Zhang X, Melo T, Ballinger JR, Rauth AM. Studies of 99mTc-BnAO (HL-91): a non-nitroaromatic compound for hypoxic cell detection. Int J Radiat Oncol, Biol, Phys. 1998;42:737–740
  14. Honess DJ, Hill SA, Collingridge DR, Edwards B, Brauers G, Powell NA, et al. Preclinical evaluation of the novel hypoxic marker 99mTc-HL91 (Prognox) in murine and xenograft systems in vivo. Int J Radiat Oncol Biol Phys. 1998;42:731–735
  15. Blower PJ, Dilworth JR, Maurer RI, Mullen GD, Reynolds CA, Zheng Y. Towards new transition metal-based hypoxic selective agents for therapy and imaging. J Inorg Biochem. 2001;85:15–22
  16. Brauers G, Archer CM, Burke JF. The chemical characterization of the tumour imaging agent 99mTc-HL91. Eur J Nucl Med. 1997;24:943
  17. Chapman JD, Engelhardt EL, Stobbe CC, Schneider RF, Hanks GE. Measuring hypoxia and predicting tumor radioresistance with nuclear medicine assays. Radiother Oncol. 1998;46:229–237
  18. Jia HM, Fang DC, Feng Y, Zhang JY, Fan WB, Zhu L. The interconversion mechanism between TcO3+ and TcO2+ core of 99mTc labeled amine-oxime (AO) complexes. Theor Chem Acc. 2008;121:271–278
  19. Zhang X, Melo T, Rauth AM, Ballinger JR. Cellular accumulation and retention of the technetium-99m-labelled hypoxia markers BRU59-21 and butylene amine oxime. Nucl Med Biol. 2001;28:949–957
  20. Hsia C, Lin C, Shen L, Chen H, Su Y. Preparation and biological characterization of novel HL91-derivative analog for hypoxic tumor imaging. Eur J Nucl Med Mol Imaging. 2007;34:S202
  21. Jackson GE, Nakani BS. Copper anti-inflammatory drugs in rheumatoid arthritis: Part 4. A potentiometric and spectroscopic study of copper(II) diaminodioxime complexes. J Chem Soc, Dalton Trans. 1996;1373–1377
  22. Ramalingam K, Zeng W, Nanjappan P, Nowotnik DP. Synthesis of functionalized 3,3,9,9-tetramethyl-4,8-diazaundecane-2,10-dione dioximes (propylene amine oximes, PnAOs). Synth Commun. 1995;25:743–752
  23. Li L, Xu Y, Su Z. The correlation of serum protein association and cellular uptake with lipophilicity and polarity of the backbone substituents of the technetium-99m-amine-oxime chelates. J Labelled Compd Radiopharm. 2007;50:91–95
  24. Dearling JL, Lewis JS, Mullen GE, Rae MT, Zweit J, Blower PJ. Design of hypoxia-targeting radiopharmaceuticals: selective uptake of copper-64 complexes in hypoxic cells in vitro. Eur J Nucl Med. 1998;25:788–792
  25. Su ZF, Ballinger JR, Rauth AM, Abrams DN, Billinghurst MWA. Novel amine-dioxime chelator for technetium-99m: synthesis and evaluation of 2-nitroimidazole-containing analogues as markers for hypoxic cells. Bioconjugate Chem. 2000;11:652–663
  26. Zhang X, Su ZF, Ballinger JR, Rauth AM, Pollak A, Thornback JR. Targeting hypoxia in tumors using 2-nitroimidazoles with peptidic chelators for technetium-99m: effect of lipophilicity. Bioconjugate Chem. 2000;11:401–407

PII: S0969-8051(09)00241-8

doi: 10.1016/j.nucmedbio.2009.09.003

Nuclear Medicine and Biology
Volume 37, Issue 2 , Pages 117-123 , February 2010