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

Nuclear Medicine and Biology

Volumn 37, Issue 2, 2010, Pages 117-123

  Sun, Xin ^a   Chu, Taiwei ^a   Wang, Xiangyun ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

BnAO; Cellular accumulation; Hypoxia marker; Labeling; Lipophilicity; Technetium 99m

Indexed keywords

UPENAZIME TC 99M; OXIME; TECHNETIUM; TECHNETIUM COMPLEX; TECHNETIUM TC 99M 4,9 DIAZA 3,3,10,10 TETRAMETHYLDODECAN 2,11 DIONE DIOXIME; TECHNETIUM TC 99M 4,9-DIAZA-3,3,10,10-TETRAMETHYLDODECAN-2,11-DIONE DIOXIME;

ANIMAL CELL; ARTICLE; CELL HYPOXIA; CELL LINE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; ISOTOPE LABELING; LIPOPHILICITY; MOUSE; NONHUMAN; STRUCTURE ANALYSIS; ANIMAL; CELL; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PATHOLOGY; SARCOMA; SYNTHESIS; THIN LAYER CHROMATOGRAPHY; TRANSITION TEMPERATURE; TRANSPORT AT THE CELLULAR LEVEL; TUMOR CELL LINE;

ANIMALS; BIOLOGICAL TRANSPORT; CELL HYPOXIA; CELL LINE, TUMOR; CELLS; CHROMATOGRAPHY, THIN LAYER; ISOTOPE LABELING; MAGNETIC RESONANCE SPECTROSCOPY; MICE; ORGANOTECHNETIUM COMPOUNDS; OXIMES; SARCOMA; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TECHNETIUM; TRANSITION TEMPERATURE;

EID: 76949086173     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2009.09.003     Document Type: Article

References (26)

1. Brown J.M., and Giaccia A.J. Tumour hypoxia: the picture has changed in the 1990s. Int J Radiat Biol 65 (1994) 95-102
2. Gray L.H., Conger A.D., Ebert M., Hornsey S., and Scott O.C.A. The concentration of oxygen dissolved in tissues at the time of irradiation as a factor in radiotherapy. Br J Radiol 26 (1953) 638-648
3. Janssen H.L., Haustermans K.M., Balm A.J., and Begg A.C. Hypoxia in head and neck cancer: how much, how important?. Head Neck 27 (2005) 622-638
4. 18F]fluoromisonidazole: a pretherapy study of 37 patients. Int J Radiat Oncol Biol Phys 36 (1996) 417-428
5. Bolla M., Gonzalez D., Warde P., Dubois J.B., Mirimanoff R.O., Storme G., et al. Improved survival in patients with locally advanced prostate cancer treated with radiotherapy and goserelin. N Engl J Med 337 (1997) 295-300
6. Abrantes A.M., Serra M.E., Murtinho D., Gonsalves A.R., and Botelho M.F. An insight into tumoral hypoxia: the radiomarkers and clinical applications. Oncol Rev 3 (2009) 3
7. Fass L. Imaging and cancer: a review. Mol Oncol 2 (2008) 115-152
8. Hansell C. Nuclear medicine's double hazard. Nonprolif Rev 15 (2008) 185-208
9. Eckelman W.C. Unparalleled contribution of technetium-99m to medicine over 5 decades. JACC Cardiovasc Imaging 2 (2009) 364-368
10. 99mTc-analog of Cu-DTS as an agent for imaging hypoxia. Nucl Med Biol 27 (2000) 391-399
11. Cook G.J., Houston S., Barrington S.F., and Fogelman I. Technetium-99m-labeled HL91 to identify tumor hypoxia: correlation with fluorine-18-FDG. J Nucl Med 39 (1998) 99-103
12. 99mTc-HL91. Effects of low flow and hypoxia on a new ischemia-avid myocardial imaging agent. Circulation 95 (1997) 1892-1899
13. 99mTc-BnAO (HL-91): a non-nitroaromatic compound for hypoxic cell detection. Int J Radiat Oncol, Biol, Phys 42 (1998) 737-740
14. Honess D.J., Hill S.A., Collingridge D.R., Edwards B., Brauers G., Powell N.A., 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 42 (1998) 731-735
15. Blower P.J., Dilworth J.R., Maurer R.I., Mullen G.D., Reynolds C.A., and Zheng Y. Towards new transition metal-based hypoxic selective agents for therapy and imaging. J Inorg Biochem 85 (2001) 15-22
16. Brauers G., Archer C.M., and Burke J.F. The chemical characterization of the tumour imaging agent 99mTc-HL91. Eur J Nucl Med 24 (1997) 943
17. Chapman J.D., Engelhardt E.L., Stobbe C.C., Schneider R.F., and Hanks G.E. Measuring hypoxia and predicting tumor radioresistance with nuclear medicine assays. Radiother Oncol 46 (1998) 229-237
18. 2+ core of 99mTc labeled amine-oxime (AO) complexes. Theor Chem Acc 121 (2008) 271-278
19. Zhang X., Melo T., Rauth A.M., and Ballinger J.R. Cellular accumulation and retention of the technetium-99m-labelled hypoxia markers BRU59-21 and butylene amine oxime. Nucl Med Biol 28 (2001) 949-957
20. Hsia C., Lin C., Shen L., Chen H., and Su Y. Preparation and biological characterization of novel HL91-derivative analog for hypoxic tumor imaging. Eur J Nucl Med Mol Imaging 34 (2007) S202
21. Jackson G.E., and Nakani B.S. 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., and Nowotnik D.P. Synthesis of functionalized 3,3,9,9-tetramethyl-4,8-diazaundecane-2,10-dione dioximes (propylene amine oximes, PnAOs). Synth Commun 25 (1995) 743-752
23. Li L., Xu Y., and 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 50 (2007) 91-95
24. Dearling J.L., Lewis J.S., Mullen G.E., Rae M.T., Zweit J., and Blower P.J. Design of hypoxia-targeting radiopharmaceuticals: selective uptake of copper-64 complexes in hypoxic cells in vitro. Eur J Nucl Med 25 (1998) 788-792
25. Su Z.F., Ballinger J.R., Rauth A.M., Abrams D.N., and Billinghurst M.W.A. Novel amine-dioxime chelator for technetium-99m: synthesis and evaluation of 2-nitroimidazole-containing analogues as markers for hypoxic cells. Bioconjugate Chem 11 (2000) 652-663
26. Zhang X., Su Z.F., Ballinger J.R., Rauth A.M., Pollak A., and Thornback J.R. Targeting hypoxia in tumors using 2-nitroimidazoles with peptidic chelators for technetium-99m: effect of lipophilicity. Bioconjugate Chem 11 (2000) 401-407